Williams v. The City of Chicago

IN THE UNITED STATES DISTRICT COURT

NORTHERN DISTRICT OF ILLINOIS

EASTERN DIVISION

CASSANDRA WILLIAMS, )

)

Plaintiff, ) No. 22 C 1084

)

v. ) District Judge Marvin E. Aspen

)

CITY of CHICAGO and ) Magistrate Judge Gabriel A. Fuentes

JASON E. BROWN, )

)

Defendants. )

MEMORANDUM OPINION AND ORDER

In this civil rights action under 42 U.S.C. § 1983, Plaintiff Cassandra Williams (“Plaintiff”)

is a Chicago police officer who has sued the City of Chicago (“the City”) and her former police

superior Jason E. Brown (“Brown”) (collectively, “Defendants”), alleging that Brown retaliated

against Plaintiff for speaking out about Brown’s having assigned Plaintiff and other officers to

guard, for six nights, the Chicago city block where Brown lived, during a period of civil unrest the

city experienced in the spring of 2020 after the death of George Floyd at the hands of police in

Minneapolis, Minnesota. Plaintiff has alleged that Brown committed a constitutional tort by

retaliating against Plaintiff for exercising Plaintiff’s First Amendment rights, and that Brown

violated the Illinois Whistleblower Act, 740 ILCS 174/5 et seq. The City is named in an

indemnification count.

The City has withheld from Plaintiff’s discovery 107 documents comprising the entirety of

the City’s Office of Inspector General (“OIG”) file of the OIG investigation into the allegations

Plaintiff made to the OIG concerning the conduct at the core of her federal lawsuit on the grounds

of privilege.1 Plaintiff, in her Third Motion to Compel Discovery (“Motion to Compel”; D.E. 77),

seeks compelled production of these 107 OIG file documents, in this matter before the magistrate

judge on a district court referral including supervision of discovery (D.E. 34).2

ANALYSIS

The City asserts the law enforcement investigatory privilege as a shield against production

of all 107 documents, and as to 17 of the 107 withheld documents, the City asserts additional

privileges, including the attorney-client privilege, the work-product doctrine, and deliberative

process privilege.3 Because the instant lawsuit arises under federal question jurisdiction, federal

courts apply the federal common law of evidentiary privileges. Hamdan v. Indiana Univ. Health

1 The Court is not reaching questions over the discoverability of any additional documents which the City

may be withholding under privilege claims that have yet to be asserted in any privilege log or that have yet

to be the subject of a Local Rule 37.2 conference. Today’s ruling concerns only the 107 documents on the

privilege log the City prepared and produced to Plaintiff (D.E. 77-3). As to the 170 additional documents

and 4,679 emails Plaintiff additionally seeks under an argument that the City waived privilege by not

supplying Plaintiff with a log, see Plaintiff’s Reply in Support of Her Third Motion to Compel Discovery

(“Reply”; D.E. 95) at 12, the Court declines to apply the waiver doctrine without first determining whether

discovery of these documents is relevant and proportional to the needs of the case, see Fed. R. Civ. P.

26(b)(1), and the Court in its discretion sees that issue as not yet ripe for decision in the instant motion to

compel.

2 The City’s privilege log (Motion to Compel, Exh. C (D.E. 77-3)) failed to specify adequately the

information for which privilege protection is sought. See David M. Greenwald & Michele L. Slachetka, 1

Testimonial Privileges § 1.69 (Thomson Reuters 2021 ed.) (“Greenwald & Slachetka”) (“A party asserting

privilege may not meet its burden through conclusory statements that the materials in question are

privileged, but instead must supply sufficient information upon which to make a determination as to each

assertion of privilege.”). The Court chose not to find in this particular matter that the City waived its

privilege claims as a result of the inadequate log. See Muro v. Target Corp., 250 F.R.D. 350, 360 (N.D. Ill.

2007) (“blanket waiver is not a favored remedy for technical inadequacies in a privilege log”). Instead, the

Court relied on the Declaration of Nathaniel Wackman (“Wackman Decl.”; D.E. 87-1) to fill some of the

informational gaps and exercised its discretion to conduct an in camera review to evaluate the privilege

claims. See Wier v. United Airlines, Inc., No. 19 CV 7000, 2021 WL 1517975, at *3 (N.D. Ill. April 16,

2021).

3 The Court does not reach the City’s claim that discovery of certain documents would violate the terms of

a protective order in place in another matter before the Court, namely State of Ill. v. City of Chicago, No.

17 C 6260 (“the Consent Decree Action”), because the documents the City claims are protected by the

Consent Decree Action’s protective order are not being ordered to be disclosed based on other asserted

privileges.

N. Hosp., Inc., 880 F.3d 416, 421 (7th Cir. 2018); Fed. R. Civ. P. 501. The Seventh Circuit’s

“general take on privileges” is to “construe [them] narrowly because they are in derogation of the

search for truth.” Valero Energy Corp. v. United States, 569 F.3d 626, 630 (7th Cir. 2009). See

also Raybestos Prod. Co. v. Younger, 54 F.3d 1234, 1245 (7th Cir. 1995) (the Seventh Circuit “has

consistently construed federal and state privilege laws narrowly, giving effect to federal

evidentiary requirements that are designed to include, not exclude, probative evidence”).

“[C]aution should be especially taken in recognizing a privilege in a federal civil rights action,

where any assertion of privilege must overcome the fundamental importance of a law meant to

protect citizens from unconstitutional state action.” Kodish v. Oakbrook Terrace Fire Prot. Dist.,

235 F.R.D. 447, 451 (N.D. Ill. 2006). “Findings regarding privilege are fact-intensive, case-

specific questions that fall within the district court’s expertise, and … as is the case with any

privilege, the one seeking its protection must carry the burden of showing that it applies.” Valero

Energy, 569 F.3d at 630. Below in Part I, we discuss the law enforcement investigatory privilege,

which is the foundation for the Court’s decision as to most of the 107 documents subject to the

Motion to Compel. Part II briefly summarizes the attorney-client privilege and work-product

doctrine, which the Court applied to a few of the withheld documents as to which those privileges

were invoked. Part III then undertakes a document-by-document analysis of the applicability of

the foregoing privileges to each of the 107 withheld documents.

I. The Law Enforcement Investigatory Privilege Protects from Civil Discovery

Documents As To Which an Interest in Non-Disclosure of Law Enforcement Files

Outweighs a Civil Litigant’s Need for Their Use in Litigation.

The Court of Appeals for the D.C. Circuit coined the phrase “law enforcement evidentiary

privilege” in addressing a claim of privilege based on the harm to law enforcement efforts which

might arise from public disclosure of information in FBI investigatory files that was being gathered

in connection with an investigation of criminal activity which “would tend to reveal law

enforcement investigative techniques or sources.” Black v. Sheraton Corp., 564 F.2d 531, 541,

545 (D.C. Cir. 1977).4 This developed into the “law enforcement investigatory privilege,” which

the Seventh Circuit recognized in Dellwood Farms, Inc. v. Cargill, Inc., 128 F.3d 1122 (7th Cir.

1997). In that case, the plaintiffs sought discovery of criminal law enforcement investigatory

materials the Department of Justice was holding for use in ongoing criminal investigations, and

the Seventh Circuit opined that “there ought to be a pretty strong presumption against lifting the

privilege” because it could “force the government to tip its hand to criminal suspects and

defendants,” and courts should not “be thrust too deeply into the criminal investigative process.”

Id. at 1125. Nevertheless, the Seventh Circuit held that this privilege “can be overridden in

appropriate cases by the need for the privileged materials” by “balancing . . . the need of the litigant

4 A few years earlier, a district court in Pennsylvania addressed the government’s withholding of police

investigation files in a civil rights case under the government’s claim of executive privilege. In assessing

whether the privilege should be lifted, the court in Frankenhauser v. Rizzo, 59 F.R.D. 339 (E.D. Pa. 1973),

created a list of 10 factors to consider in balancing the public interest in the confidentiality of information

from a potentially ongoing criminal case against the needs of a civil litigant to obtain data:

(1) the extent to which disclosure will thwart governmental processes by discouraging

citizens from giving the government information; (2) the impact upon persons who have

given information of having their identities disclosed; (3) the degree to which

governmental self-evaluation and consequent program improvement will be chilled by

disclosure; (4) whether the information sought is factual data or evaluative summary; (5)

whether the party seeking the discovery is an actual or potential defendant in any criminal

proceeding either pending or reasonably likely to follow from the incident in question; (6)

whether the police investigation has been completed; (7) whether any intradepartmental

disciplinary proceedings have arisen or may arise from the investigation; (8) whether the

plaintiff's suit is non-frivolous and brought in good faith; (9) whether the information

sought is available through other discovery or from other sources; and (10) the importance

of the information sought to the plaintiff’s case.

Id. at 344. Although Black, 564 F.2d 531, did not mention Frankenhauser factors, the D.C. appellate court

later referred to them as “illustrative” and “helpful.” See In re Sealed Case, 856 F.2d 268, 272 (D.C. Cir.

1988); Friedman v. Bache Halsey Stuart Shields, Inc., 738 F.2d 1336, 1342 (D.C. Cir. 1984). The Fifth

Circuit is the only other appellate court to discuss the Frankenhauser factors, see In re U.S. Dep’t of

Homeland Sec., 459 F.3d 565, 570 (5th Cir. 2006), but various district courts around the country have cited

to the Frankenhauser factors with approval, as we note below.

who is seeking privileged investigative materials [] against the harm to the government.” Id. at

1124-25. Dellwood Farms did not delineate the balancing factors to be considered in determining

whether the law enforcement investigatory privilege should be lifted, instead leaving this

“particularistic and judgmental task . . . to the discretion of the district judge.” Id. We find that

the law enforcement investigatory privilege applies to the OIG file being withheld in this case, and

we apply the Dellwood Farms balancing to determine as to which documents the privilege must

be lifted.

A. The Law Enforcement Investigatory Privilege Applies to the OIG File Being

Withheld in this Case, But Not in Blanket Fashion.

A threshold dispute presented by the Motion to Compel is whether the law enforcement

investigatory privilege should also apply broadly to “civil” investigations conducted by a law

enforcement agency, such as the OIG’s file at issue in this case. Plaintiff contends that the OIG

investigation into her allegations here is no more than an “internal employment investigation,” to

which the law enforcement investigatory privilege does not apply. Motion to Compel at 4. In

response, the City argues that the investigatory privilege protects civil as well as criminal law

enforcement investigatory files from civil discovery.5

5 Notably, the City never explicitly asserts, in its brief or in the Wackman Declaration, that OIG’s

investigation into Plaintiff’s complaint to OIG about Defendant Brown’s alleged conduct at issue in this

lawsuit is a criminal investigation. Defendant’s Response in Opposition to Plaintiff’s Third Motion to

Compel Discovery (“Opp.”; D.E. 87) at 5-7, citing Rodriguez v. City of Chicago, 329 F.R.D. 182, 189 (N.D.

Ill. 2019). The Wackman Declaration nonetheless makes clear that the OIG’s charge under the Chicago

Municipal Code (“CMC”) includes criminal investigations as well as investigations of employee

misconduct; per the CMC, OIG may partner with a law enforcement agency in a joint criminal investigation

or may conduct such an investigation on its own and present the case to a criminal prosecutor for the lodging

of charges. Wackman Decl. ¶ 10. Nevertheless, for purposes of deciding the Motion to Compel, the Court

will presume that the investigation is in fact “civil” and not criminal, as the Court examines the City’s

arguments as the City has presented them.

1. The Law Enforcement Investigatory Privilege’s Protection from Civil

Discovery Is Not Limited Strictly to the Agency’s Criminal Files.

The Court rejects Plaintiff’s contention that the law enforcement investigatory privilege

cannot apply to the OIG file being withheld in this case because the privilege does not extend to

law enforcement civil investigations, such as internal investigations of employee misconduct. The

investigative file sought in litigation of a civil antitrust lawsuit in Dellwood Farms was the U.S.

Department of Justice’s criminal investigative file from its celebrated “lysine” price-fixing

conspiracy investigation involving Archer Daniels Midland Co.6

Writing for the Seventh Circuit in Dellwood Farms, Judge Posner opined “that there ought

to be a pretty strong presumption against lifting the [law enforcement investigatory] privilege,”

because “[o]therwise the courts will be thrust too deeply into the criminal investigative process,”

which involve matters “firmly in the executive branch, subject only to such limited judicial

intervention as may be necessary to secure constitutional and other recognized legal rights of

suspects and defendants.” 128 F.3d at 1125 (emphasis added). The Dellwood Farms panel added

that civil litigants who seek disclosure of law enforcement investigative files should not have “a

right to force the government to tip its hand to criminal suspects and defendants by disclosing the

fruits of the surreptitious (but presumably lawful) surveillance that the FBI conducted.” Id.

(emphasis added). Civil discovery requests that effectively ask district courts to “mediate”

between civil litigants’ desires to expedite their civil litigation “and the government’s conduct of

its criminal investigation” place such courts outside “a proper judicial role.” Id. (emphasis added).

The heart of our concern is with the principle that the control of criminal

investigations is the prerogative of the executive branch, subject to judicial

6 The lysine investigation was enshrined in popular culture by the film The Informant! (Warner Bros. 2009),

starring Matt Damon.

intervention only to protect rights – and no rights of the plaintiffs were invaded by

the government’s assertion of its law enforcement investigatory privilege.

Id. at 1126 (emphasis added).

Dellwood Farms involved a criminal file and concerns about judicial interference in a

criminal investigation, but many of the same concerns exist as well with respect to civil discovery

of a law enforcement agency’s civil investigation. The public and the government agency still

could be harmed if certain of the agency’s file materials from a civil or employment investigation

are disclosed, and courts allowing civil discovery of certain investigative file materials still may

be unduly interfering with executive branch functions by doing so. The key to determining the

privilege’s applicability lies in examining the degree to which withheld documents may trigger

those concerns, and the nature of the civil litigant’s need for the materials. As we explain further

below, it is this balancing of interests – and not that an investigation is purely civil in nature – that

is the decisive or revelatory “thing” concerning this privilege. See William Shakespeare, Hamlet,

Prince of Denmark, Act II, Scene II (ca. 1599-1601) (“The play’s the thing Wherein I’ll catch the

conscience of the King.”) (reprinted in Mortimer Adler, Great Books of the Western World, Vol.

27 at 46 (Encyclopaedia Britannica 1952).

2. The Law Enforcement Investigatory Privilege’s Coverage of Civil

Investigative Files Is Not a Blanket Protection Against Civil Discovery of

All Such Files Even If an Investigation Is Active and Ongoing.

The Court also rejects the City’s proposed approach barring all discovery of all OIG civil

investigatory files in blanket fashion. Blanket protection is not justified on grounds that a law

enforcement agency conducted the investigation and that the investigation is ongoing. Although

the privilege applies to civil investigatory materials, the City’s assertion that Dellwood Farms

established a “presumption” that here precludes all of the OIG files, Opp. at 4-7, goes too far.

Dellwood Farms did not suggest that a blanket protection should apply to all agency files

even from a criminal investigation. Instead, Dellwood Farms held that disclosure of materials in

the face of a law enforcement investigatory privilege claim depends on a “balancing” of “the need

of the litigant” against “the harm to the government if the privilege is lifted.” Id. at 1125. Nothing

about this aspect of Dellwood Farms instructs us that the required balancing should be anything

but individualized, and such an instruction would run counter to the Seventh Circuit’s rule that

privileges should be “construe[d] narrowly,” Valero Energy, 569 F.3d at 630, and that a “claim of

privilege cannot be a blanket claim; it must be made and sustained on a question-by-question or

document-by-document basis.” United States v. White, 950 F.2d 426, 430 (7th Cir. 1991) (internal

citations and quotations omitted) (applying rule against blanket claims of privilege to attorney-

client privilege). See also LKQ Corp. v. Kia Motors Am., Inc., No. 21 C 3166, 2023 WL 3200236,

at *4 (N.D. Ill. May 2, 2023) (applying rule against blanket privilege claims to assertions of work-

product protection).

The fact that, according to the City, the OIG investigation is ongoing or incomplete does

not change the rule against blanket application of the privilege. Although the City argues that its

confidentiality interests in the OIG investigation would be harmed irreparably by discovery in that

discovery will make the materials “public,” Opp. at 8, they will not be made “public” by discovery.

Unfiled discovery is not public, and even filed discovery is subject to sealing upon a sufficient

showing under the applicable Seventh Circuit law. See Baxter Int’l, Inc. v. Abbott Labs., 297 F.3d

544, 545-46 (7th Cir. 2002). Nor will the withheld documents’ “use[] in pending litigation,” Opp.

at 8, categorically render them undiscoverable by the law enforcement investigatory privilege;

Dellwood Farms blocks civil discovery only if the balancing of interests comes out against

discoverability. The ongoing character of an investigation is just one factor in the balancing.

The authorities relied on by the City for heightening the Dellwood Farms presumption

against civil discovery of materials from ongoing investigations do not hold differently. See Opp.

at 7, citing Clark v. Powe, Nos. 07 C 1616, 07 C 5251, 2008 WL 4686151 (N.D. Ill. May 30,

2008), Myhre v. Ditzler, No. 05 C 50074, 2006 WL 8462189 (N.D. Ill. Feb. 21, 2006), and Hill v.

City of Chicago, No. 06 C 6772, 2011 WL 320204 (N.D. Ill. Jan. 31, 2011). In Clark, the district

court cited Dellwood Farms and found that amid an ongoing criminal investigation of a suspect

whose identity was unknown to the civil litigant seeking to compel disclosure, the suspect’s

identity was properly withheld under the law enforcement investigatory privilege. 2008 WL

4686151, *1-3. In Myhre, the magistrate judge found that the balancing of interests weighed

against civil discovery of a broad array of police investigative files whose disclosure threatened

an ongoing criminal prosecution then pending in state court. 2006 WL 8462189, at *3-4. And in

Hill, the district court cited Dellwood Farms and undertook an in camera review of “cold case”

police files including the identities of two new murder suspects identified through DNA analysis

long after the plaintiff alleged he was wrongfully prosecuted in the case; the court recognized the

value of this information to plaintiff but held it to be protected by the law enforcement

investigatory privilege in view of the “serious public safety issues” that could result from

inadvertent public disclosure of the information. 2011 WL 320204, at *1-2.

In Clark, Myhre and Hill, civil discovery of files from ongoing criminal investigations

posed specific threats of harm to those investigations, as opposed to the City’s more generalized

and somewhat speculative concern here that “disclosure of an active investigation file would be

more likely to compromise the integrity of the investigation due to potential disclosure of witness

identities and other information that could alter the final outcome of the investigation.” Opp. at 7.

As for the City’s further contention that in ongoing investigations, “[t]he OIG’s employees must

be allowed to have frank communications without fear that their honest thoughts and mental

impressions will be made public to private litigants,” id. at 8-9, the Court agrees that this valid

concern lies at the root of “executive privilege” and of the evolution of the law enforcement

investigatory privilege. But the Seventh Circuit’s required balancing of interests addresses that

concern, providing a mechanism for protecting against that sort of damage to the public interest,

while allowing for consideration of a civil litigant’s need for information the law enforcement

agency wants to protect as privileged. See Dellwood Farms, 128 F.3d at 1125. Clark, Myhre and

Hill stand for including the ongoing nature of an investigation in the interest balancing discussed

further in Part B. below, and not for blanket protection of file materials simply because an

investigation is ongoing.

B. The Scope of the Law Enforcement Investigatory Privilege’s Protection of Law

Enforcement Agency Investigative Documents from Discovery Depends on a

Balancing of Interests.

Although the Seventh Circuit has not employed the 10-factor balancing test in

Frankenhauser, see supra n.4, a few courts in this district have nevertheless discussed all 10 factors

(without citing to Frankenhauser), while other courts focused on particular factors (that are

subsumed within Frankenhauser) based on the importance to the case before them to determine

whether the law enforcement investigatory privilege should be overcome.

In Lewis v. City of Chicago, No. 04 C 3904, 2004 WL 2608302, at *1 (N.D. Ill. Nov. 16,

2004), for example, the court held that the law enforcement investigatory privilege asserted by the

City “must yield in this case to the plaintiff’s need for disclosure of the materials contained” in the

Complaint Register (“CR”) file maintained by the City’s Office of Professional Standards, where

the CR file “may contain evidence probative of plaintiff’s civil rights claim under Section 1983.”

Similarly, in Santiago v. City of Chicago, No. 09 C 3137, 2010 WL 1257780, at *4 (N.D. Ill. Mar.

26, 2010), the court determined that the law enforcement investigatory privilege was overcome by

the civil rights plaintiff’s need for the information in the Chicago Police Department’s internal

investigation CR files; the court also noted that the City’s concerns could be addressed by an

appropriate protective order. In Rodriguez, the court held that the law enforcement investigatory

privilege did not apply to certain documents from the City’s Independent Police Review Authority

and Civilian Office of Police Accountability because the City did “not identify a specific harm

beyond a concern that the withheld materials might influence future witness and officer statements

to investigators if they are disseminated,” and they “reflect[ed] purely factual information and do

not appear to reveal any confidential investigatory techniques or to discuss any on-going criminal

investigation that might otherwise justify the claim of privilege.” 329 F.R.D. at 189.

By contrast, the court in Jones v. Brennan, No. 18 C 1213, 2019 WL 2287986, at *4 (N.D.

Ill. May 29, 2019), found that the information at issue was irrelevant to the plaintiff’s case and

allowed the government agency to withhold it. Similarly, in Kampinen v. Individuals of Chicago

Police Dep’t, No. 00 C 5867, 2002 WL 238443, at *4 (N.D. Ill. Feb. 19, 2002), the court allowed

materials to be withheld under the law enforcement investigatory privilege where the court’s in

camera review revealed that, the information was “inextricably intertwined with confidential

[Secret Service] Agency functions,” and “it ha[d] little bearing upon [the plaintiff’s] constitutional

claims.” In addition, in Doe v. Hudgins, 175 F.R.D. 511, 515 (N.D. Ill. 1997), the court allowed

the underlying files to be withheld primarily because there were criminal proceedings pending

against the defendant.7

7 The balancing test applied by courts in this district is consistent with the approach other federal courts

within the Seventh Circuit have taken. For example, in Anderson v. Marion County Sheriff’s Dep’t, 220

F.R.D. 555, 564-67 (S.D. Ind. 2004), the court allowed discovery of a law enforcement agency’s civil

internal investigation file after applying the Frankenhauser factors and emphasizing that “[f]irst and

foremost” the case did not involve a criminal investigation, but rather “an investigation relating to non-

criminal disciplinary matters between employees,” and that “the importance of the information to the

The Court will undertake the Dellwood Farms balancing as to the 107 withheld documents in Part

III below, with a few exceptions in which the Court had to apply the attorney-client privilege,

work-product doctrine, or deliberative process privilege. These protections are discussed briefly

below in Part II.

II. The Attorney-Client Privilege and Work-Product Doctrine Provide Other Avenues

for Protection Against Civil Discovery of Certain Materials.

The City also has invoked the attorney-client privilege, the work-product doctrine, and the

deliberative process privilege as to a few of the 107 withheld documents. “The attorney-client

privilege protects communications made in confidence by a client and a client’s employees to an

attorney, acting as an attorney, for the purpose of obtaining legal advice.” Sandra T.E. v. South

Berwyn Sch. Dist. 100, 600 F.3d 612, 618 (7th Cir. 2010), citing Upjohn Co. v. United States, 449

U.S. 383, 394-99 (1981), and Trammel v. United States, 445 U.S. 40, 51 (1980). The work-product

doctrine “is distinct from and broader than the attorney-client privilege.” Appleton Papers, Inc. v.

E.P.A., 702 F.3d 1018, 1024 (7th Cir. 2012), quoting United States v. Nobles, 422 U.S. 225, 238

n. 11 (1974). It protects from disclosure “documents prepared by attorneys in anticipation of

litigation for the purpose of analyzing and preparing a client’s case,” as well as “an attorney’s

thought processes and mental impressions,” in order to “limit[] the circumstances in which

attorneys may piggyback on the fact-finding investigation of their more diligent counterparts.”

Sandra T.E., 600 F.3d at 618, 621-22. “The Seventh Circuit has explained that the test for

‘anticipation of litigation’ is ‘whether, in light of the nature of the document and the factual

situation in the particular case, the document can be fairly said to have been prepared or obtained

plaintiff’s case—[which] has been described by courts as the most crucial” weighed in favor of disclosure

of the material. Id. at 564, 567. See also Palmer v. City of Decatur, No. 17-CV-3268, 2019 WL 13156163,

at *4 (N.D. Ill. July 22, 2019) (“In analyzing an investigatory privilege claim, the court, keeping in mind

that there is a strong presumption that the privilege applies, balances the need of the litigant seeking the

privileged materials against the harm to the government if the privilege is lifted.”).

because of the prospect of litigation.’” Hankins v. Alpha Kappa Alpha Sorority, Inc., 619 F. Supp.

3d 828, 837 (N.D. Ill. 2021), quoting Binks Mfg. Co. v. Nat’l Presto Indus., Inc., 709 F.2d 1109,

1118-19 (7th Cir. 1983) (citing 8 Charles Alan Wright, Arthur R. Miller & Richard L. Marcus,

Federal Practice and Procedure § 2024 (3d ed. 2021)) (emphasis in Binks). Work-product

protection does not apply to “materials prepared in the ordinary course of business – even if

prepared at a time when litigation was reasonably anticipated” or “merely because there is a remote

prospect of future litigation” or because litigation does eventually ensue. Hankins, 619 F. Supp.

3d at 837 (internal citations and quotations omitted). As for documents sought to be withheld under

the deliberative process privilege, the Court in Part III is permitting them to be withheld based on

other applicable privileges. As a result, the Court does not reach the deliberative process privilege

claims at all.8

III. The Court’s Balancing of Interests As to the 107 Withheld Documents Results in the

Motion To Compel Being Granted in Part and Denied in Part.

The Court’s approach to applying the balancing of interests to determine whether the 107

withheld documents are covered by the relevant, asserted privileges in this case was guided not

only by Dellwood Farms, but also by the federal courts’ more general prescription that evidentiary

privileges are to be construed narrowly. The City at one point suggests that the law enforcement

investigatory privilege bars discovery unless Plaintiff can show a “compelling” justification for

allowing the discovery. See Opp. at 8. The Court disagrees. The burden to establish the privilege’s

coverage is on the City, and not Plaintiff, Shaffer v. American Med. Ass’n, 662 F.3d 439, 446 (7th

Cir. 2011), and Plaintiff’s sole access to the content of the 107 withheld documents here is through

8 The Court therefore does not reach Plaintiff’s argument that the deliberative process privilege may not be

claimed by state and municipal entities in a lawsuit arising under federal question jurisdiction. See Motion

to Compel at 10, citing Murdock v. City of Chicago, 565 F. Supp. 3d 1037, 1043 (N.D. Ill. 2021).

a privilege log that the Court has found wanting. Dellwood Farms and the cases applying it allow

discovery if a civil litigant’s need for the materials outweighs the public and agency interest against

discovery, and not upon the civil litigant showing a “compelling” justification or need.

The Court agreed with the City that certain other factors weighed in the City’s favor under

Dellwood Farms, and the Court balanced those factors against Plaintiff’s need for the materials.

These factors include the ongoing and active nature of the OIG investigation. They also include a

form of baseline interest, on the part of the City and OIG, in the confidentiality of every document

in the OIG investigatory file. In addition to the OIG’s interest in non-disclosure of its

investigators’ thought processes in choosing which documents to include in the investigatory file,

or which documents the investigators chose to “follow up” on, OIG has a more generalized interest

in the overall confidentiality of the file, stemming from the confidentiality of OIG investigations

and file documents per the Chicago Municipal Code and Illinois statutes. See Wackman Decl. ⁋⁋

13-16 (reciting Chicago Municipal Code and Illinois statutory provisions concerning the

confidentiality of OIG investigations). This statutory baseline interest in confidentiality is not a

zero in the Dellwood Farms balancing, and where Plaintiff’s need for a particular OIG file

document is zero or is extremely low, the City has carried its burden on the law enforcement

investigatory privilege. In baseball, the tie goes to the runner, but the Court is not finding any ties

here. In each and every instance of Dellwood Farms balancing undertaken as to the 107

documents, the Court weighed the respective interests, with the privilege applying wherever the

City’s (and the public’s) interest in keeping the investigatory file documents confidential

outweighed Plaintiff’s need for them in the litigation. Plaintiff’s need was substantial enough to

outweigh those confidentiality interests, so that the City did not carry its burden, with respect to

witness interview transcripts and summary interview memoranda, but not with respect to many or

all routine investigative materials in which investigators or OIG attorneys documented their receipt

of certain materials, internally requested those materials from other City departments, summoned

City employees for interviews, or communicated with City employees’ counsel to schedule the

interviews or to discuss issues such as transcript errata. Plaintiff’s need for these more workaday

investigatory documents was very low or non-existent, so the City’s baseline interest in the

confidentiality of the OIG investigative files weighed in favor of the law enforcement investigatory

privilege’s protection of those documents, and thus the City carried its burden, even as to publicly

available materials, such as news accounts or court documents that found their way into OIG’s

files without analytical staff commentary, annotation or discussion.

The document-by-document balancing analysis required by Dellwood Farms is set forth

below.

Document No. 1. The Court agrees that this “Case Relationship Report” falls within the

Court’s limited application of the law enforcement investigatory privilege because it maps and

documents OIG’s investigative planning and steps relative to its investigation of Plaintiff’s OIG

complaint, which she lodged before she filed suit in this action. See Wackman Decl. ¶ 41. The

City claims the law enforcement investigatory privilege claim as to certain portions of the

document, namely the report’s discussion of conversations between Plaintiff’s counsel (Thomas

Needham) and OIG staff about access to OIG file materials. Plaintiff’s need for the recitation of

a conversation her counsel had with OIG is minimal, if not zero. Because Plaintiff’s need is

minimal and disclosure of information OIG chose to place in its investigatory plan is, in some

small measure, a disclosure of OIG investigative thought processes, the Court finds that the

Dellwood Farms balancing favors applying the law enforcement investigatory privilege to deny

the Motion to Compel as to Document No. 1. The City also invokes the work-product doctrine

and deliberate process privilege as to this document, but the Court does not reach those claims, as

the document may be withheld under the law enforcement investigatory privilege.

Document No. 2. The City claims law enforcement investigatory privilege over this OIG

anonymous complaint report, which recites the content of the anonymous complaint about events

largely overlapping with the core of Plaintiff’s allegations in the lawsuit. With this document

being a report of an anonymous complaint that contains little or nothing that Plaintiff has not

already alleged, or that she already knows she has alleged, the Court sees Plaintiff’s need for this

document as extremely low or nil. Moreover, although disclosure of this document has a low

potential to harm OIG, its investigations, or the public, disclosure still would mean the transmittal

of an anonymous complaint to third parties, in contravention of OIG’s baseline interest in the

confidentiality of its investigative files under the CMC. For these reasons, the Court denies the

Motion to Compel as to Document No. 2 under the Dellwood Farms balancing.

Document No. 3. The City’s claim of law enforcement investigatory privilege over the

OIG report of its March 31, 2021, interview of Plaintiff is not sustainable because the Dellwood

Farms balancing favors discovery. This report is not of an anonymous complaint. It names

Plaintiff and describes her complaint against Defendant Brown in a way that, again, tracks

Plaintiff’s civil complaint in the lawsuit and thus has zero potential to impede the OIG’s

investigative function in any way; moreover, Plaintiff has a strong interest in discovering records

within the City’s possession concerning her own prior statements, which have the potential to be

used to impeach her. The Motion to Compel is granted as to this document.

Document No. 4. The Motion to Compel is denied as to this short, one-paragraph OIG

investigative report reflecting the transmission of certain information by Plaintiff’s counsel, Mr.

Needham, to OIG in support of Plaintiff’s OIG complaint. The City’s interest in preserving the

confidentiality of this external communication in the OIG file is low, but the in camera review

indicated no articulable need by Plaintiff for this document.

Document No. 5. This OIG interview report summarizes a somewhat more detailed OIG

interview of Plaintiff on May 21, 2021, in the presence of Mr. Needham and at his office. The

Motion to Compel is granted as to this document for the same reasons stated above as to Document

No. 3.

Document Nos. 6, 7. The Motion to Compel is denied as to these two brief OIG reports

describing investigative steps OIG took early in its investigation. Discovery of these materials

would disclose OIG’s investigative steps and methodology in a way that outweighs Plaintiff’s

relatively low need for this information, according to the Court’s judgment on in camera review.

The Court is permitting these records to be withheld without reaching the City’s further claim, as

to Document No. 7, that it cannot be produced in this litigation under the terms of a protective

order in the Consent Decree Action.

Document Nos. 8-14. The Motion to Compel is denied as to these brief OIG reports that

are little more than notes to the OIG files documenting the fact that various witness interviews

were conducted or that various documentary information was obtained as a part of the OIG

investigation. Discovery of these materials would disclose OIG’s investigative steps and

methodology in a way that, although minimal, outweighs Plaintiff’s even lesser need for this

information, which in the Court’s judgment is not particularly useful or revealing, or which is

duplicative of other information Plaintiff will receive from the OIG file, such as interview reports

and transcripts.

Document No. 15. The OIG’s file note indicating another external communication with

Plaintiff’s counsel, and including transmittal to OIG of a publicly available document, minimally

includes investigative mental impressions. Plaintiff’s need for this document is zero because she

already has it, and her knowledge of OIG’s inclusion of the document in its file is of low or no

value to her. The Motion to Compel is denied as to this document.

Document Nos. 16-25. The Motion to Compel is denied as to these documents, which are

similar in character to Document Nos. 9-14 and may be withheld under the law enforcement

investigatory privilege for the same reasons stated above with reference to Document Nos. 9-14.

Document No. 26. This document is a copy of a publicly available news report. Allowing

a document like this to be withheld under the law enforcement investigative privilege is highly

counterintuitive. Privilege claims are not ordinarily sustainable as to documents that have been

exposed to the wider world and are accessible to the wider world. But Plaintiff has virtually zero

need for this document. Comparing Plaintiff’s need against the OIG’s baseline interest in the

statutory confidentiality of all of its investigative files, the OIG’s interest in confidentiality – even

in something as innocuous as a news report – prevails in the Dellwood Farms balancing. To hold

otherwise would be to allow a civil litigant to thumb through a law enforcement investigatory file

in discovery and obtain documents for which the litigant has no need at all. The OIG also

articulated an interest in preventing disclosure of this document because such disclosure would

reveal “what information in the public domain the OIG followed up on as it conducted its

investigation.” Wackman Decl. ¶ 66. As dubious as that interest may be, it is greater than zero.

The Motion to Compel is denied as to Document No. 26.

Document No. 27. This document is an OIG file note documenting OIG’s having obtained

a copy of a publicly available court document. The Motion to Compel is denied for the same

reasons the Court denied it as to Document No. 15.

Document No. 28. This report concerning information OIG sought and was unable to

obtain about the circumstances or communications surrounding Defendant Brown’s demotion

presents a close call, because the persons and avenues the OIG chose to pursue to seek this

information represent investigative choices and methods. Nonetheless, on in camera review, the

Court applies the Dellwood Farms balancing to grant the Motion to Compel as to this document,

because in the Court’s judgment, the absence of information on this subject (or the OIG’s inability

to obtain it from these sources) has a significant enough relevance to the claims and defenses in

this case so that Plaintiff’s need for it outweighs the OIG’s interest in withholding it.

Document No. 29. This document presents another close call, but one falling in favor of

non-disclosure. The OIG file report documents the fact that OIG obtained certain information

from Brown through his attorney, and it reflects investigative steps and methods; the Court did not

see Plaintiff’s need for this particular information as outweighing OIG’s interest in the

confidentiality of those steps and methods. The Motion to Compel is denied as to this document.

Document No. 30. The Motion to Compel is granted as to this OIG report documenting

the fact that OIG interviewed Defendant Brown on May 17, 2022. The fact that OIG would

interview Brown is no great investigatory revelation, and nor is the content of the document

making a record of the fact that the interview took place. Plaintiff’s need for the document is

minimal but enough to justify discovery.

Document Nos. 31-32. The Motion to Compel is denied as to these OIG file notes

documenting the fact that certain other interviews took place, as they reflect the OIG’s decisions

and choices as to whom to interview and when, in a manner that outweighs Plaintiff’s very low

need for information concerning the mere fact that these interviews took place.

Document No. 33. This email chain includes external communications between the OIG

representatives and counsel, James McKay, for several of the police officers being interviewed,

about the scheduling of interviews. Disclosure of this document may reveal the timing of certain

interviews, as well as the identity of persons being interviewed, but it also reveals details of the

form and manner of OIG’s communication with counsel for interview subjects. OIG’s need for

confidentiality of this information is relatively low, but it is significant enough to outweigh

Plaintiff’s even lesser need for this document, which contains no substantive information. The

Motion to Compel is denied as to this document.

Document Nos. 34-38. These communications involve purported transcript errors

communicated to OIG by attorney McKay in his capacity as legal representative for certain

interviewed witnesses (and Document No. 39 is an internal OIG communication on that subject),

and the sending of video interview invitations to certain witnesses. They are non-substantive

external communications, but they were generated in the context of OIG’s investigative process,

and disclosure of them discloses more of the OIG’s confidential investigative milieu. With

Plaintiff’s need for these documents at little or none, the Motion to Compel is denied as to these

documents.

Document No. 39. This OIG file memorandum is addressed to two OIG attorneys

(Inspector General Deborah Witzburg and Deputy Inspector General William Marback) and is

signed by an OIG investigator whom the OIG identifies as an attorney (Wackman Decl. ¶ 79). The

document does not seek legal advice explicitly, as it describes “factual information on an issue

with four transcripts,” as the City stated in the privilege log. Id. The Court does not agree with

OIG that the document is attorney-client privileged because “potential legal implications for OIG’s

investigation and any eventual disciplinary proceedings or appeal from a disciplinary decision” so

that the memo “was drafted to provide legal advice,” id. but the Court on in camera review sees

the document as a request to obtain legal advice from the addresses, who were OIG lawyers and

included the OIG herself. The Motion to Compel is denied as to Document No. 39, which is

protected by the attorney-client privilege. The Court does not reach the other privilege claims

asserted by the City as to this document.

Document Nos. 40-44. An email from Mr. Needham, as Plaintiff’s counsel, to OIG

attaching two sets of text messages Plaintiff believed to be relevant to the OIG investigation, and

the two sets of messages, are contained in the first three of these five documents. The latter two

documents are Mr. Needham’s email to OIG attaching photos and a video that Plaintiff shared

with OIG in support of her OIG complaint. Plaintiff’s need for these materials is low because she

provided them to OIG through her counsel. Plaintiff no doubt already has the texts or has seen

them. In the absence of any clear need of Plaintiff for these documents, the Court sees the OIG’s

minimal interest in the confidentiality of its files, and of its choices as to what to include in those

files, as outweighing Plaintiff’s need, so the Motion to Compel is denied as to these five documents

under the Dellwood Farms balancing.

Document No. 45. This document is Plaintiff’s personnel file. The fact that this file is

found within OIG’s investigative files may be of some methodological significance, but on

balance, the Court did not see any reason why the law enforcement investigatory privilege ought

to block Plaintiff’s discovery of the contents of her own personnel file. The Motion to Compel is

granted as to this document.

Document No. 46. The OIG’s formal notification of interview, provided to city employees

who will be interviewed, is much like a notice of deposition, but the Court could not see any need

for discovery, by Plaintiff, of these forms and thus denies the Motion to Compel as to this

document.

Document Nos. 47-49. These documents are among the most important, for Plaintiff, in

the OIG investigative file. They are the sworn transcripts of interviews of three witnesses whom

Plaintiff initially identified, in her March 31, 2021, interview with OIG (as reflected in Document

No. 3), as being among the six police officers (other than Plaintiff) on the watch team allegedly

assigned to a post at Defendant Brown’s home in June 2020. The City claims that these documents

must be withheld under the law enforcement investigatory privilege because disclosure to Plaintiff

under a protective order would reveal “the complete substance of their testimony” and would allow

these or other witnesses to shape or shade their testimony “by knowing what testimony is available

to OIG to corroborate or contradict their testimony.” Wackman Decl. ¶¶ 87-89. But that assertion

does not carry the day on the City’s effort to invoke the law enforcement investigatory privilege

as a shield against discovery of these transcripts. These transcripts are of OIG interviews of

Chicago Police Department members who have a contractual right to receive the transcripts within

72 hours after OIG receives them. Id. ¶ 32. The fact that the interviewed officers receive these

transcripts does not operate as a “waiver” of the law enforcement investigatory privilege, as the

OIG fears, id. ¶ 33, but it does bear on the balancing undertaken by the Court in considering the

privilege claim under Dellwood Farms. Witnesses who received these transcripts, and who in

some cases had their counsel submit errata to OIG to correct purported errors in the transcripts,

can be presumed to have retained possession of them and to know full well what prior testimony

OIG has of theirs. Denying Plaintiff discovery of these transcripts would deny Plaintiff the prior

sworn statements by persons whose accounts are integral to her claims in this case, as these

witnesses allegedly were placed on the same June 2020 detail at Brown’s home as was Plaintiff.

Plaintiff’s need for the transcripts is therefore very high. Additionally, the Court is unpersuaded

that the Dellwood Farms balancing should come out in favor of withholding these transcripts under

the law enforcement investigatory privilege based on the OIG’s contention that their discovery in

this matter under a protective order would reveal the information they provided, “including the

names of other persons with knowledge,” and would reveal “how OIG has sequenced interviews

and investigative steps OIG has taken.” Id. ¶¶ 87-89. Civil discovery of these transcripts may

reveal all of those things, but again, those revelations ought to shock no one – OIG set out to

interview the other officers who, according to what Plaintiff herself told OIG, were placed on the

June 2020 detail, and to the degree that their transcripts might reveal the names of other persons

with knowledge, that is the very nature of federal civil discovery. Finally, the City correctly notes

that the police collective bargaining agreement requires the statements of a police officer to be

disclosed only to that individual police officer, but disclosure to Plaintiff of the statements in civil

discovery, even under a protective order, creates the possibility that information from various

witness statements could find their way to other witnesses during the discovery process. Opp. at

6; Wackman Decl. ¶ 29. The City argues that such disclosure might “chill” the willingness of

witnesses to cooperate with or speak to OIG in the future, id., but the degree to which the City’s

employees might be “chilled” in cooperating based on civil discovery of their statements is too

speculative to outweigh Plaintiff’s need for the documents. Moreover, as OIG reminds us, a City

employee’s cooperation with OIG is hardly a voluntary endeavor: “All City employees have a

duty to cooperate with OIG, and OIG regularly compels interviews of City employees …. Failure

to cooperate with an OIG investigation by a City employee is also grounds for discharge or other

discipline.” Wackman Decl. ¶ 11. Admittedly, an employee’s cooperation can take different

forms, some less forthcoming or less helpful to the investigation than others. But as to these and

other witness statements or transcripts referenced further below, Plaintiff’s need for the

information outweighs the City’s assertions, per the law enforcement investigatory privilege, about

potential harms visited on OIG or on the public interest by civil discovery of these materials. The

Motion to Compel is granted as to these transcripts.

Document No. 50. This document is a report by the OIG’s Center for Information

Technology & Analytics analyzing Chicago Police Department data to answer three questions with

respect to police deployment at Brown’s home city block during the relevant period of May 31 to

June 10, 2020. The Court views this data analysis, and the means OIG used to gather the data, as

law enforcement methodology that ought to be protected under the law enforcement investigatory

privilege. Moreover, Plaintiff’s need for the data analysis is low because, if she has not already,

she may simply pose these three questions – which are obvious, although the Court is deliberately

omitting them from this discussion in view of the applicability of the privilege – as interrogatories

that defendants, or at least the City, is bound to answer, knowing of course that OIG as a city

agency previously gathered it through the CITA process. The details of the CITA process are not

needed by Plaintiff, who has other access to the results of the analysis through ordinary discovery

requests. Having denied the Motion to Compel based on the law enforcement investigatory

privilege, the Court does not reach the City’s deliberative process privilege claim as to this

document.

Document No. 51. This document consists of several documents. The attorney-client

privilege supports withholding the first one, an internal OIG email from OIG General Counsel

Wackman to OIG investigators about the nature and content of the Police Department’s June 2,

2020 “action plan.” The document comes very close to being non-privileged for relating no more

than underlying facts, but a portion of it does include a comment by attorney Wackman to the staff

concerning how the action plan might be analyzed or interpreted. That is enough for the Court to

deem the cover email from Mr. Wackman attorney-client privileged. The remainder of the

document consists of a Police Department action plan and other planning memoranda. The law

enforcement investigatory privilege applies to these documents and shields them from discovery

upon the in camera review and interest balancing. The Court’s in camera review showed that the

planning documents went into great detail about the Chicago Police Department’s plans to deal

with protests and demonstrations anticipated in the city after the death of George Floyd, including

what resources would be allocated. Plaintiff may well find this information useful as a part of her

effort to prove that deploying her to Defendant Brown’s home was contrary to the Police

Department’s priorities at the time, but that need does not outweigh the very substantial interest,

not so much by OIG but by the City and its Police Department, in being able to formulate effective

actions plans to deal with planned public unrest without having to be concerned that the plans will

be disclosed in federal discovery stemming from lawsuits not about the plans themselves, but about

how one supervisory officer chose to deploy his subordinates, or about allegations that he retaliated

against Plaintiff for having discussed the deployment with third parties. The Motion to Compel is

thus denied as to the documents contained in Document No. 51 for the foregoing reasons, without

the Court reaching the other grounds asserted by the City for protection from discovery.

Document Nos. 52, 53. These documents are document requests, on formal OIG letterhead,

from the OIG to two city departments. The Court could not easily identify any significant need

by the Plaintiff for these documents, which are internal to the City and which represent

investigative measures and methods to a sufficient degree to sustain the City’s claim of law

enforcement investigatory privilege. The Motion to Compel is denied as to these documents.

Document Nos. 54, 55. These documents are similar in form and character to Document

No. 46, and the Motion to Compel as to this document is denied for same reasons the Court denied

it as to Document No. 46.

Document No. 56. This document consists of a short email exchange between the OIG and

Plaintiff’s counsel Needham, attaching the civil complaint filed in this action. For the same

reasons the Court stated above as to Document No. 15, the Motion to Compel is denied as to this

document.

Document Nos. 57, 58. These documents are similar in form and character to Document

No. 46, and the Motion to Compel as to these documents is denied for the same reasons the Court

denied it as to Document No. 46.

Document No. 59. The Court could not determine if this document is a non-identical copy

of the Plaintiff’s personnel file in Document No. 45, but like that document, it related entirely to

Plaintiff, and the OIG has identified it as a personnel file. Wackman Decl. ¶ 99. The Motion to

Compel is granted as to this document for the same reasons the Court granted the Motion as to

Document No. 45.

Document No. 60. This document consists of a set of Police Department reports supplied

to the OIG in response to a document request OIG made to the Department. In the Court’s view

on in camera review, the first several pages of the document contain the form and manner of OIG

document requests in a manner that sufficiently triggers the law enforcement investigatory

privilege over means and methods. The Court denies the Motion to Compel as to those pages and

grants it only as to the last page (Bates number 506),9 which is a substantive Police Department

submission of information to OIG about the absence of certain law enforcement records

9 The four-digit references to Bates pages are a shortened version of the longer Bates ranges, which are

stated for the 107 withheld documents as OIG-22-cv-1084-0001-1232.

(specifically from the Department’s Narcotics Division) about police deployments related to the

George Floyd protests. Defendant Brown, as the then-commander of the Narcotics Division, is

one of the signers of this February 28, 2022, document. The Court sees Plaintiff as having a need

for the information contained in this document, so she might be better able to explore in discovery

the Narcotics Division’s inability to produce such documents. Plaintiff’s need for this portion of

the document outweighs the law enforcement interest in non-disclosure under the Dellwood Farms

balancing.

Document No. 61. Other than the first two pages, which consist of document-request-type

communications that the Court has held to be within the law enforcement investigatory privilege

and not within Plaintiff’s needs in this case, this document is a “mobilization check-in” list

apparently of Narcotics Division police personnel who “checked” in as mobilized for duty during

the George Floyd protests as of June 2, 2020. OIG’s boilerplate recitation that discovery of this

document would reveal information OIG obtained during its investigation and/or investigative

steps and processes (Wackman Decl. ¶ 101) does not outweigh, under Dellwood Farms, Plaintiff’s

need for this document, insofar as it may reveal which Narcotics Division members were deployed

to the Floyd protests, as opposed to the detail at Defendant Brown’s house, in June 2020.

Accordingly, the Motion to Compel is granted as to Bates pages 509-529 and denied as to the

remainder of this document.

Document No. 62. This document appears to contain Police Department disciplinary

records concerning Plaintiff and Defendant Brown. These types of records have been the subject

of extensive litigation in this matter, and the City previously has been ordered to produce them, or

records substantially of their character. Because Plaintiff already has access to these CR files from

other sources, Plaintiff’s need for Document No. 62 is low, and it is outweighed by the City’s

interest in protecting its investigatory methods as they might be revealed by the version of the CR

files contained in the OIG file of its investigation into Plaintiff’s OIG complaint about Brown. The

Motion to Compel is denied as to Document No. 62.

Document No. 63-65. These documents are similar in form and character to Document No.

46, and the Motion to Compel as to these documents is denied for the same reasons the Court

denied it as to Document No. 46.

Document No. 66-68. These are additional transcripts from two more police officers whom

Plaintiff said were part of the June 2020 detail at Brown’s home, and a third transcript (Document

No. 68) from a police officer who was not himself detailed to Defendant Brown’s house, or at least

was not alleged to have been so deployed, but who was transferred from the Narcotics Division to

a midnight shift at the 11th Police District, after having been part of various discussions among

officers about the Brown detail after-the-fact and after having raised concerns about it himself

within the Police Department including with Brown. The Motion is granted as to these transcripts,

for the same reasons the Court granted it as to Document Nos. 47-49. In addition, although the

witness in Document No. 68 was not himself detailed or alleged to have been detailed to Defendant

Brown’s house, this officer’s allegations of like retaliation are highly relevant to this case for

purposes of the Dellwood Farms balancing.

Document Nos. 69-71. These documents are similar in form and character to Document

No. 46, and the Motion to Compel as to this document is denied for the same reasons the Court

denied it as to Document No. 46.

Document No. 72. This transcript of OIG’s interview with Defendant Brown’s former

administrative assistant, an officer not alleged to have been deployed to Brown’s home in June

2020, has a lesser relevance to the matter than do the other transcripts in the OIG file, but the

Court’s in camera review of this transcript confirms that Plaintiff’s need for this weighs in favor

of discovery, so the Motion to Compel is granted as to this document, for the same reasons the

Court granted the Motion as to Document Nos. 47-49.

Document No. 73. This document is a publicly available news report, and the Motion to

Compel is denied for the same reasons as the Court denied it with respect to Document No. 26.

Document No. 74. This document is similar in form and character to Document Nos. 52

and 53, and the Motion to Compel as to this document is denied for the same reasons the Court

denied it as to Document Nos. 52 and 53.

Document No. 75. This document is a publicly available court document, and the Motion

to Compel is denied as to this document for the same reasons the Court denied it as to Document

No. 27, the OIG file note about acquisition of a publicly available document for inclusion in the

investigative file. Both documents represent the content of the OIG file, and the OIG’s baseline

interest in the confidentiality of its file outweighed Plaintiff’s need for the documents, as that need

was zero.

Document No. 76. Aside from the first page, a Police Department communication similar

in character to Document Nos. 52 and 53, as to which the Court has denied the Motion, this

document contains the substantive responses of members of the Police Superintendent’s office and

other Chicago police executive-level personnel reflecting that they possessed only scant

documents in their files concerning Defendant Brown’s change of assignment from commander of

the Narcotics Division to the position of lieutenant in the 9th Police District in May 2022. The

Motion is granted as to all but the first page of this document, for the same reasons the Court

granted the Motion to Compel as to the relevant portion of Document No. 60.

Document No. 77. This document is similar in form and character to Document No. 46,

and the Motion to Compel as to this document is denied for the same reasons the Court denied it

as to Document No. 46.

Document No. 78. For the same reasons the Court granted the Motion to Compel as to

Document Nos. 47-49, the Motion to Compel is granted as to this transcript of the OIG interview

of Defendant Brown, which is highly relevant to the claims and defenses in this case and as to

which Plaintiff has a significant need, as confirmed by the Court’s in camera review.

Document No. 79. This document is similar in form and character to Document No. 46,

and the Motion to Compel as to this document is denied for the same reasons the Court denied it

as to Document No. 46.

Document No. 80. This transcript of OIG’s interview with an officer who was a

subordinate of Plaintiff in the Narcotics Division in June 2020, and who has not been alleged to

have been deployed to Brown’s home in June 2020, has a far lesser relevance to the matter than

do the other transcripts in the OIG file, but the Court’s in camera review confirms that Plaintiff’s

need for this transcript outweighs the City’s interest in withholding it, so the Motion to Compel is

granted as to this document, for the same reasons the Court granted the Motion to Compel as to

Document Nos. 47-49 and 72.

Document No. 81. Plaintiff’s need for this transcript of OIG’s interview with a very high-

ranking Chicago police executive, who was among Defendant Brown’s direct superiors during

Brown’s time as Narcotics Division commander as of June 2020, and with whom Brown had a

longstanding professional relationship in the Police Department, is sufficient to outweigh the

City’s interest in withholding it. Among other things, Defendant Brown’s superior stated certain

striking recollections – or lack thereof – concerning Brown’s alleged deployment of Narcotics

Division officers in June 2020, and concerning Brown’s May 2022 demotion. The Motion to

Compel is granted as to this document for the same reasons the Court granted it as to Document

Nos. 47-49, 72, and 80. But as to Bates pages 1059-67, which consist of the special events/unrest

action plan as to which the Court has previously denied the Motion to Compel on the ground that

it is protected by the law enforcement investigatory privilege, the Court denies the Motion to

Compel for the same reasons stated as to Document No. 51 with regard to such action plans.

Document No. 82. This document is similar in form and character to Document Nos. 52

and 53, and the Motion to Compel as to this document is denied for the same reasons the Court

denied it as to Document Nos. 52 and 53.

Document No. 83. This document appears to be Defendant Brown’s personnel file from

the Police Department. The Court is not aware of whether this document has already been

discovered in the ordinary course of the litigation, and the Court is unsure of the extent of

Plaintiff’s need for the information, which is a sensitive employment record. Nonetheless, the

Court sees the discoverability of the contents of this OIG file document as best addressed through

party discovery, as it is available (or unavailable, as the case may be), through party discovery.

Courts applying the law enforcement investigatory privilege have considered “whether the

information sought is available through other discovery or from other sources,” Santiago, 2010

WL 1257780, at *2, and the Court applies that consideration here to deny the Motion to Compel

as to Document No. 83 under the Dellwood Farms balancing.

Document No. 84. This document consists of a string of text messages, apparently from

June 2020, between Plaintiff and Defendant Brown and pertaining to the alleged deployment of

Plaintiff to Brown’s home at that time. Plaintiff appears to possess the information already. The

Motion to Compel is denied as to this document under the Dellwood Farms balancing.

Document No. 85. This is a report of an interview of a Police Department member with

responsibility for managing the Department’s overall personnel deployment during the June 2020

period of civil unrest in Chicago. The City asserts that this report was “authored by an attorney”

within OIG “based on notes from another attorney,” so that OIG can “make judgments on whether

OIG has the necessary proof to recommend discipline against City employees” and “in anticipation

of potential litigation regarding imposed discipline or an appeal of imposed discipline.” However,

the fact that an attorney conducted or participated in a witness interview, or that an attorney

prepared the interview memorandum from another’s notes, does not establish that the document is

privileged or relates to the rendering of legal services. The Court’s in camera review of the

document showed that it contained or communicated no legal advice or attorney mental

impressions. The document is simply an interview memorandum relating non-privileged

underlying facts about how the City deployed police, at a very high level, in June 2020. That is

not enough to justify work-product or attorney-client protection. As for the law enforcement

investigatory privilege, the City’s claims for protection of this information mirror those it asserted

to shield documents like interview transcripts from discovery, and the Court finds those reasons

unpersuasive for the same reasons it granted the Motion as to documents including Nos. 47-49,

72, and 80. In the case of Document No. 85, Plaintiff’s need for this relatively brief but informative

factual information about the degree to which the Police Department’s response to the June 2020

unrest involved a substantial citywide strain on the Department and its personnel outweighs the

City’s interest in withholding the document. Under the Dellwood Farms balancing, the Motion to

Compel is granted as to this document.

Document No. 86. This document is a letter to OIG from former Police Superintendent

David Brown reflecting his response to a question about the reasons for Defendant Brown’s change

in assignment from Narcotics Division commander to 9th Police District lieutenant. The degree

to which discovery of this document reveals protectible OIG investigative mental impressions,

plans and direction is low, and Plaintiff’s need for the response of Chicago’s highest-ranking police

official to this question is high. This is sufficient to tip the Dellwood Farms balancing in favor of

discovery, particularly given the information elsewhere in the OIG file (Document No. 81)

discussing the nature of former Superintendent Brown’s role in the demotion of Defendant Brown.

The Motion to Compel is granted as to this document.

Document No. 87. This document is an OIG “case initiation report” that is of little or no

value to Plaintiff and reveals, to some extent, OIG’s investigative processes to an extent justifying

denial of the Motion to Compel under the Dellwood Farms balancing. The Court shields this

document from discovery without reaching the City’s deliberative process privilege claim.

Document No. 88. This document appears to be a duplicate of Document No. 3, and the

Motion to Compel is granted as to this document for the same reasons the Court granted it as to

Document No. 3.

Document Nos. 89-91. These documents consist of email communications between OIG

staff and personnel of COPA, a police agency that investigates allegations of officer misconduct,

and between OIG and the Chicago Police Department Bureau of Internal Affairs, which has a

similar charge. The Court had difficulty conceiving of any need by Plaintiff for these documents,

which reflect an internal City investigative process. The Motion to Compel is denied as to these

documents under the Dellwood Farms balancing. The Court shields these documents from

discovery without reaching the City’s deliberative process privilege claim.

Document No. 92. This document is an internal OIG memorandum prepared by an OIG

staff member who happened to be an attorney. Wackman Decl. ¶ 132. The memorandum distilled

information OIG received from the witness whose interview transcript is reflected in Document

No. 68 into a bullet-point style listing of aspects of that witness’s allegations in a state-court

lawsuit, intended to obtain the response and the legal advice of the OIG general counsel. Thus

Document No. 92 could be said to reflect the attorney’s analysis of the court documents discussed

in the memorandum. As such, the Court sustains OIG’s assertion of the attorney-client privilege

over this document, and the Motion to Compel is denied on this basis.

Document No. 93. This document is an iteration of the OIG plan for investigation into

Plaintiff’s allegations, and the Motion to Compel is denied as to this document, for the same

reasons the Court denied the Motion as to Document No. 1. The Court does not reach the City’s

attorney-client, work-product and deliberative process privilege claims as to this document.

Document No. 94. This document is identical to a portion of Document No. 51 as to which

the Motion to Compel was denied, and the Motion to Compel is denied here for the same reasons

the Court denied it with respect to Document No. 51.

Document No. 95. This document consists largely of email communications between OIG

attorneys, including about steps OIG took to communicate with BIA and COPA. The Court agrees

with the City that these documents are in the nature of communications intended to be confidential

and made for the purposes of rendering legal services. Thus, they are protected by the attorney-

client privilege, and the Motion to Compel is denied as to these documents, without reaching the

City's other privilege claims as to this document.

Document Nos. 96, 97. These external communications between OIG and Plaintiff’s

counsel, and between the Police Department general counsel and Plaintiff’s counsel, are non-

substantive such that Plaintiff’s need for them is too low to outweigh the OIG’s baseline interest

in the confidentiality of its investigative file. The Motion to Compel is denied as to these

documents under the Dellwood Farms balancing and the law enforcement investigatory privilege.

Document No. 98. This document is similar in form and character to Document No. 95,

and the Motion to Compel is denied for the same reasons the Court denied it as to Document No.

95.

Document No. 99. This document is identical to the CITA data analysis report as to which

the Court denied the Motion to Compel with respect to Document No. 50, so the Motion to Compel

is denied as to Document No. 99 for the same reasons.

Document No. 100. This document is an investigative timeline of events, and although it

contains information that Plaintiff may find useful, her need for that component information does

not outweigh, per Dellwood Farms, the agency’s interest in protecting its investigative processes,

methods, plans and procedures. The Motion to Compel is denied as to this document.

Document Nos. 101, 102. These documents relate entirely to internal OIG investigative

processes and methods, and they are of little or no use to Plaintiff in this matter, so the Dellwood

Farms balancing comes out squarely in support of denying the Motion to Compel, and it is denied

as to these documents, without the Court reaching the deliberative process privilege claim the City

asserts as to Document No. 101.

Document No. 103. This document is the set of attorney notes that were used to prepare

the OIG interview memorandum in Document No. 85, as to which the Motion was granted. There

is a difference between attorney notes and a summary interview memorandum, and even the grant

of the Motion to Compel as to Document No. 85 does not change the fact that Document No. 103

contains attorney or investigator notes that are protected under the law enforcement investigatory

privilege so long as the Dellwood Farms balancing comes out in favor of the privilege’s

applicability, which it does here because the production of Document No. 85 (the OIG file

memorandum of the interview) significantly lessens Plaintiff’s need for the notes. Accordingly,

the Dellwood Farms balancing favors denying the Motion to Compel as to Document No. 103, and

it is so denied. Alternatively, the attorney notes were prepared by an OIG attorney for confidential

communication to another OIG attorney or staff member for the purpose of creating the interview

memorandum, and that purpose relates to the rendering of legal services, so Document No. 103 is

protected from discovery by the attorney-client privilege. The Court’s in camera review of the

document does not indicate that it was prepared in anticipation of litigation; it was instead prepared

as a part of the ordinary course of the OIG internal investigation. So the work-product doctrine

does not apply to Document No. 103. For the foregoing reasons, the Motion to Compel is denied

as to Document No. 103, without reaching the other privileges asserted by the City as to this

document but not discussed above.

Document No. 104. This document is highly similar in form and character to Document

No. 102, and the Motion to Compel is denied as to this document for the same reasons the Court

denied it as to Document No. 102.

Document No. 105. This document is a revised investigative plan and is shielded from

discovery by the law enforcement investigatory privilege, for the same reasons the Court found

the privilege applicable to Document Nos. 1 and 93. The Motion to Compel is denied, without the

Court reaching the attorney-client, work-product, and deliberative process privilege claims the

City asserts as to this document.

Document No. 106. This document is identical to Document No. 91, and the Motion to

Compel is denied as to this document for the same reasons the Court denied the Motion to Compel

as to Document No. 91.

Document No. 107. This document is highly similar in form and character to Document

Nos. 52 and 53, and the Motion to Compel is denied as to this document for the same reasons the

Court denied it as to Document Nos. 52 and 53.

CONCLUSION

For the foregoing reasons and per the individualized discussion above of each of the 107

withheld documents, the Motion to Compel is partially granted and partially denied as stated

above. The law enforcement investigatory privilege does not offer blanket protection against civil

discovery of a law enforcement agency’s civil or criminal investigative file. Dellwood Farms and

other judicial decisions discussing or applying this judge-made privilege do not offer a set of clear

standards for the interest balancing that courts must undertake, and nor do these decisions place

clear boundaries around the kinds of law enforcement files that could fall within the privilege’s

protection. Courts instead are instructed that the document-by-document interest balancing needed

to evaluate and apply the law enforcement investigatory privilege is a “particularistic and

judgmental task” that is “confided to the discretion of the district judge.” Dellwood Farms, 128

F.3d at 1125. The magistrate judge has sought to do so here, exercising the substantial discretion

afforded to magistrate judges with respect to discovery management. See Jones v. City of Elkhart,

Ind., 737 F.3d 1107, 1115 (7th Cir. 2013).

SO ORDERED.

ENTER:

SLC A. Fixe

GABRIEL A. FUENTES

United States Magistrate Judge

DATED: May 11, 2023

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