Jackson v. United States

UNITED STATES DISTRICT COURT

FOR THE SOUTHERN DISTRICT OF ILLINOIS

DENNIS D. JACKSON,

Petitioner,

v. Civil No. 21-cv-361-JPG

Criminal No 17-cr-40052-JPG

UNITED STATES OF AMERICA,

Respondent.

MEMORANDUM AND ORDER

This matter comes before the Court on petitioner Dennis D. Jackson’s motion to vacate,

set aside or correct his sentence pursuant to 28 U.S.C. § 2255 (Doc. 1) and his amended motion

(Doc. 11). The Government has responded to the amended motion (Doc. 16), and Jackson has

replied to that response (Doc. 19).

I. Background

In June 2018, a grand jury returned the Third Superseding Indictment charging Jackson

with two counts of distribution of a mixture and substance containing methamphetamine in

violation of 21 U.S.C. § 841(a)(1) and (b)(1)(C) (Counts 1 and 2), one count of distribution of 5

grams or more of actual methamphetamine in violation of 21 U.S.C. § 841(a)(1) and

(b)(1)(B)(viii) (Count 3), one count of possession with intent to distribute 50 grams or more of

actual methamphetamine in violation of 21 U.S.C. § 841(a)(1) and (b)(1)(A)(viii) (Count 4), one

count of possessing a firearm in furtherance of a drug trafficking crime in violation of 18 U.S.C.

§ 924(c) (Count 5), and one count of possessing a firearm (actually, four firearms) as a felon in

violation of 18 U.S.C. § 922(g)(1) (Count 6).

The Government also filed an information under 21 U.S.C. § 851 alleging two prior

felony drug offenses—two Illinois convictions, one for unlawful possession with intent to deliver

cocaine and one for unlawful possession of MDMA—to seek an enhanced statutory sentencing

range. As a result of the information, under the version of 21 U.S.C. § 841(b)(1) then in place,

Jackson’s statutory sentencing range on Counts 1 and 2 became no more than 30 years, on Count

3 became 10 years to life, and on Count 4 became mandatory life.

As part of the investigation of Jackson that led to these charges, the Government used a

confidential source (“CS”) to make three controlled purchases from Jackson. The Government

used evidence obtained in those controlled purchases to obtain a search warrant of Jackson’s

home, and the search yielded methamphetamine, other drugs, cash, scales, and multiple loaded

firearms. Before trial, the CS escaped from the jail where he was being held on unrelated

charges. The CS was captured two days before Jackson’s trial. Even so, the Court—over

Jackson’s objection—allowed the Government to show the jury recordings depicting the

controlled purchases, reasoning that they were not hearsay because they were not being offered

for their truth and thus did not violate the Sixth Amendment’s Confrontation Clause. The Court

gave an appropriate limiting instruction. The Court also denied Jackson’s motion to suppress,

where he raised several Fourth Amendment arguments relating to the search of his home.

In July 2018, a jury found Jackson guilty of Counts 1 through 4 but could not reach a

decision on Counts 5 and 6, which the Government eventually dismissed. At sentencing in

November 2018, the Court sentenced Jackson to 360 months in prison on Counts 1 and 2, 480

months on Count 3, and mandatory life on Count 4.

Jackson appealed his conviction to the Court of Appeals for the Seventh Circuit, arguing

that the Court erred by (1) admitting the recording and law enforcement officers’ related

testimony about the recording into evidence at trial and (2) not reducing his sentence under the

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First Step Act of 2018, which took effect less than a month after his sentencing and reduced the

statutory minimum sentence on Count 4 to 25 years for those in Jackson’s circumstances. See

United States v. Jackson, 940 F.3d 347 (7th Cir. 2019). On October 8, 2019, the Court of

Appeals affirmed Jackson’s sentence in all respects. See id. at 349-54. Jackson did not seek a

writ of certiorari from the Supreme Court.

II. § 2255 Motion

In his § 2255 motion, mailed on March 29, 2021, and docketed April 5, 2021, the

petitioner raises the following claims:

Ground 1: Counsel was constitutionally ineffective in connection with the motion to

suppress, in making stipulations with which Jackson did not agree, in failing to

object to certain evidence, in connection with the appeal, and in connection with

various other trial and sentencing matters;

Ground 2: The Court denied Jackson due process when it admitted recordings of the CS even

after the CS was apprehended and was available to testify at trial, failed to have a

hearing on his motion to suppress, failed to appreciate chain of custody issues,

and subjected him to double jeopardy;

Ground 3: The Government obtained evidence through illegal eavesdropping and colluded

with state law enforcement to bring federal charges;

Ground 4: The Court wrongfully denied the motion to suppress, and the Government used

evidence from illegal eavesdropping to obtain a warrant to search Jackson’s

home.

Following review pursuant to Rule 4(b) of the Rules Governing Section 2255

Proceedings for the United States District Courts (“§ 2255 Rules”), the Court determined

Jackson was plainly not entitled to relief on his assertions:

• that the Court erred by admitting the recordings of the CS into evidence without giving

Jackson an opportunity to cross-examine the CS in violation of the Confrontation Clause;

• that counsel failed to challenge the chain of custody of the drug evidence; and

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• that Jackson was subjected to double jeopardy by state and federal prosecutions for the

same conduct.

Jackson then amended his § 2255, mailed January 5, 2022, and docketed January 12,

2022, to add additional arguments:

Amendment Claim 1: Counsel was constitutionally ineffective when he failed to argue that

Jackson’s prior convictions charged in the § 851 information did not support

enhanced sentencing ranges under 21 U.S.C. § 841(b)(1);

Amendment Claim 2: Counsel was constitutionally ineffective when he stated to the jury that

Jackson was “not innocent” when Jackson had instructed him to take the position

that he was innocent of all charges; and

Amendment Claim 3: Counsel was constitutionally ineffective when he failed to seek

suppression of the evidence found in the search and its fruits on the grounds that

the search violated his Fourth Amendment rights because it violated state law

regarding searches.

In his amended motion, Jackson further argues that his original § 2255 motion was timely. He

notes that the Clerk of Court docketed his original motion on April 5, 2021, months beyond the

one-year deadline as calculated under 28 U.S.C. § 2255(f). He argues that the deadline should

be equitably tolled.

The Court ordered the Government to respond to the unresolved grounds alleged for

§ 2255 relief. The Government contends that Jackson’s motion and its amendment are

untimely, that he has procedurally defaulted a number of his arguments, and his arguments have

no merit.

The parties’ arguments are now before the Court.

III. Analysis

The Court must grant a § 2255 motion when a defendant’s “sentence was imposed in

violation of the Constitution or laws of the United States.” 28 U.S.C. § 2255(a). However,

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“[r]elief under § 2255 is available ‘only in extraordinary situations, such as an error of

constitutional or jurisdictional magnitude or where a fundamental defect has occurred which

results in a complete miscarriage of justice.’” United States v. Coleman, 763 F.3d 706, 708 (7th

Cir. 2014) (quoting Blake v. United States, 723 F.3d 870, 878-79 (7th Cir. 2013)). It is proper to

deny a § 2255 motion without an evidentiary hearing if “the motion and the files and records of

the case conclusively demonstrate that the prisoner is entitled to no relief.” 28 U.S.C.

§ 2255(b); see Shipman v. United States, 925 F.3d 938, 943 (7th Cir. 2019); Sandoval v. United

States, 574 F.3d 847, 850 (7th Cir. 2009).

The Court first turns to the issue of timeliness, then to Jackson’s substantive arguments.

A. Timeliness

A petitioner seeking relief under § 2255 must file his motion within the one-year statute

of limitations set forth in § 2255(f). The one-year limitations period runs from the latest of four

events:

(1) the date on which the judgment of conviction becomes final;

(2) the date on which the impediment to making a motion created by governmental action

in violation of the Constitution or laws of the United States is removed, if the movant was

prevented from making a motion by such governmental action;

(3) the date on which the right asserted was initially recognized by the Supreme Court, if

that right has been newly recognized by the Supreme Court and made retroactively

applicable to cases on collateral review; or

(4) the date on which the facts supporting the claim or claims presented could have been

discovered through the exercise of due diligence.

28 U.S.C. § 2255(f). Thus, the Court asks when Jackson’s one-year period began and whether

his motion fell within that period.

It appears that the applicable trigger for the one-year period for Jackson is found in

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§ 2255(f)(1); he has not asserted any governmental impediment to making a motion, any right

newly recognized by the Supreme Court, or any newly discovered evidence. Indeed, Jackson

concedes that § 2255(f)(1) triggers the one-year period but argues that equitable tolling should

apply.

1. Date Conviction Becomes Final, § 2255(f)(1)

Where a petitioner files a direct appeal but does not seek review by the United States

Supreme Court, a judgment of conviction becomes final for § 2255 purposes when the time

expires for filing a petition for a writ of certiorari contesting the appellate court’s decision.

Clay v. United States, 537 U.S. 522, 524-25 (2003). The period for filing such a petition expires

90 days after the court of appeals enters judgment or denies a petition for rehearing. S. Ct. R.

13(1) & (3). The Court of Appeals affirmed Jackson’s sentence on October 8, 2019, so his

deadline for filing a petition for a writ of certiorari expired 90 days later—on January 6, 2020.

Thus, the one-year period under § 2255(f)(1) expired on January 6, 2021. Jackson’s original

§ 2255 motion, deemed under the mailbox rule to have been filed March 29, 2021, and his

amended § 2255 motion, deemed to have been filed January 6, 2022, were beyond this deadline.

See Houston v. Lack, 487 U.S. 266, 276 (1988) (mailbox rule).

2. Equitable Tolling

Jackson concedes that his original § 2255 motion was late but urges the Court to consider

it timely under the doctrine of equitable tolling. The one-year limitations period is not

jurisdictional and can be equitably tolled in an appropriate case. Holland v. Florida, 560 U.S.

631, 645 (2010) (considering § 2244(d)’s similar one-year limitation for § 2254 petitions);

Ademiju v. United States, 999 F.3d 474, 477 (7th Cir. 2021). Tolling is appropriate where a

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petitioner has been reasonably diligent in pursuit of his rights but some extraordinary

circumstance prevented him from timely filing his motion. Holland, 560 U.S. at 649; Ademiju,

999 F.3d at 477. The extraordinary circumstances must be “both extraordinary and beyond [the

petitioner’s] control.” Menominee Indian Tribe of Wis. v. United States, 477 U.S. 250, 257

(2016); accord Ademiju, 999 F.3d at 477; Lombardo v. United States, 860 F.3d 547, 552 (7th

Cir. 2017). “[T]he threshold necessary to trigger equitable tolling is very high, lest the

exceptions swallow the rule.” United States v. Marcello, 212 F.3d 1005, 1010 (7th Cir. 2000).

Generally, neither counsel’s ineptitude nor garden-variety excusable neglect by itself

warrants equitable tolling of the § 2255 one-year limitations period. Ademiju, 999 F.3d at 477;

Lombardo, 860 F.3d at 552. Nor does a petitioner’s limited access to a prison law library.

Ademiju, 999 F.3d at 478. On the other hand, abandonment by counsel without notice can

justify equitable tolling. Id. at 477; see Maples v. Thomas, 565 U.S. 266, 281-83 (2012). The

key question is whether counsel, as the client’s agent, made a mistake that the client will have to

live with, or whether counsel ceased functioning as the client’s agent without notice to the client

that the client was on his own. Maples, 565 U.S. at 283.

As a preliminary matter, the Government argues that, in light of Nutraceutical Corp. v.

Lambert, 139 S. Ct. 710 (2019), equitable tolling cannot apply to the one-year deadline to file a

§ 2255 motion. Nutraceutical held that the 14-day deadline in Federal Rule of Civil Procedure

23(f) to appeal class action certification or decertification decisions is not subject to equitable

tolling because Rule 26(b) expresses the intent to rigorously enforce appeal deadlines. Id. at

715. The Government claims the one-year deadline to file a § 2255 motion is also a “mandatory

claim-processing rule” not subject to equitable exceptions. However, Nutraceutical did not

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expressly overrule Holland, which clearly holds equitable tolling may apply to the § 2255 one-

year deadline, and the Government has not pointed to any expression of Congress’s intent not to

allow equitable tolling in that circumstance. Until the Supreme Court or the Court of Appeals

for the Seventh Circuit holds that Holland is no longer good law for the proposition, this Court

will continue to apply equitable tolling to § 2255 motions in appropriate circumstances.

Jackson argues that the deadline should be equitably tolled because of his unique

circumstances. First, Jackson claims his attorney abandoned him when he failed to advise

Jackson that his appeal had been decided on or around October 8, 2019, and when he failed to

respond to Jackson’s many inquiries into the status of his case or take certain actions Jackson had

requested. Because of counsel’s lack of communication, Jackson did not know his one-year

period had begun to run. In his original March 2021 § 2255 motion he claimed that he “just

recently found out [his sentence] was affirmed,” Pet.’s § 2255 Mot. ¶ 18 (Doc. 1).

Second, he claims he had essentially no access to the law library from November 2019 to

March 2021 because of lockdowns, COVID-19 prevention measures at United States

Penitentiary-Lee, where he was housed, and his own illness from COVID-19 from December

2020 to February 2021. This assertion is supported at least for part of that time by a

memorandum from Jackson’s unit manager stating that Jackson had limited access to the library

and his legal work since March 2020, when pandemic restrictions began, but had access as of

December 7, 2020 (Doc. 1 at 13). When this access began, Jackson claims it was essentially

ineffective because an entire unit of 50 inmates had access to one legal computer to access Lexis

for only two hours a day only three times a week, making it effectively unavailable for those who

were not the first to arrive and claim the computer. Consequently, he had no way to

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independently research whether the Court of Appeals had decided his case. He does not say

how he eventually discovered his appeal had been decided.

The Court assumes Jackson’s allegations are true that his counsel failed to notify him

when his appeal had been decided and that Jackson’s description of his access to legal resources

until March 2021 is accurate. Regardless of whether counsel’s conduct qualifies as

“abandonment” or mere negligence—the failure to keep a client apprised of the status of a

case—the Court does not believe it is sufficient, by itself, to justify equitable tolling.

Nevertheless, in combination with other circumstances, the Court believes equitable

tolling is appropriate to render Jackson’s original § 2255 motion timely. While counsel’s lack

of response to Jackson’s communications should have tipped Jackson off that he might be on his

own and should try to locate independently the information he was seeking, other factors over

which Jackson had no control made it exponentially more difficult to do this. Conditions at the

prison, whether pre-COVID-19 lockdowns or COVID-19 disease prevention measures,

essentially deprived Jackson of his ability to diligently follow up on the status of his appeal at the

law library during the relevant time period. The Court does not criticize the prison for the

restrictions it imposed—the COVID-19 pandemic overwhelmed prison resources with the

monumental challenges of preventing the disease from spreading, making sure inmate’s essential

needs were met, and otherwise ensuring the safety and functioning of the facility. But the Court

believes it can be appropriate in certain cases to accommodate the difficulties inmates faced

because of those restrictions by extending or equitably tolling deadlines.

Additionally, the Court is cognizant that Jackson received a life sentence, a serious matter

which the Court does not take lightly. Accordingly, it is inclined to broadly construe the

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doctrine of equitable tolling to entertain arguments that were arguably timely to ensure a life

sentence was properly imposed. For these reasons, Jackson’s case warrants equitable tolling of

the one-year deadline until March 29, 2021, the day Jackson signed and mailed his original

§ 2255 motion. It will deem that motion timely.

3. Relation Back of Amended § 2255 Motion

Jackson’s amended § 2255 motion, mailed January 5, 2022, is a different story. Jackson

filed his amended § 2255 motion nearly a year after his one-year deadline expired and months

after the conditions that impeded his filing a § 2255 motion improved enough for him to be able

to file a § 2255 motion. Therefore, in order for the claims in his amended § 2255 motion to be

timely, they must relate back to his original § 2255 motion, which the Court deems timely

because of equitable tolling.

An amendment to a § 2255 motion may relate back to the original § 2255 motion where

“the amendment asserts a claim or defense that arose out of the conduct, transaction, or

occurrence set out—or attempted to be set out—in the original pleading.” Fed. R. Civ. P.

15(c)(1)(B); see § 2255 Rule 12 (applying Federal Rules of Civil/Criminal Procedures so long as

they are not inconsistent with statutes or § 2255 Rules); see also Fed. R. Civ. P. 81(a)(4). An

amendment will not relate back, however, “when it asserts a new ground for relief supported by

facts that differ in both time and type from those the original pleading set forth.” Mayle v. Felix,

545 U.S. 644, 650 (2005). At one point the Court of Appeals for the Seventh Circuit held that

any new argument in an amended petition attacking the same trial or conviction as the original

motion did arise out of the same “conduct, transaction, or occurrence” and would therefore relate

back. See Ellzey v. United States, 324 F.3d 521, 527 (7th Cir. 2003), abrogated by Mayle, 545

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U.S. at 659. However, in Mayle, the Supreme Court rejected that rule and adopted a far

narrower view of “conduct, transaction, or occurrence.” Mayle, 545 U.S. at 659, 664.

Mayle considered whether an amended § 2254 motion asserting ineffective assistance of

counsel in relation to an alleged wrongful coercion of pretrial statements in violation of the Fifth

Amendment related back to an original pro se § 2254 motion asserting the wrongful admission

of videotaped testimony in violation of the Sixth Amendment. Id. at 648. The Supreme Court

concluded that whether claims arose out of the same “conduct, transaction, or occurrence”

depended on whether they shared a “common core of operative facts.” Id. at 664. Thus, the

petitioner’s self-incrimination claims were discrete from his Confrontation Clause claims and did

not arise out of the same “conduct, transaction, or occurrence” for relation back purposes. See

id. at 661.

The Court now turns to Jackson’s claims in his amended § 2255 motion to see if they

share a common core of operate facts with those in his original motion.

a. Amendment Claim 1

The first claim in Jackson’s amended § 2255 motion is that his counsel was

constitutionally ineffective because he failed to argue at sentencing that Jackson’s prior

convictions charged in the § 851 information were inadequate to support enhanced sentencing

ranges under 21 U.S.C. § 841(b)(1) using the categorical approach. This argument is based on

cases decided before Jackson’s original § 2255 motion—Mathis v. United States, 579 U.S. 500

(2016), United States v. Elder, 900 F.3d 491 (7th Cir. 2018), and United States v. Ruth, 966 F.3d

642 (7th Cir. 2020), cert. denied, 141 S. Ct. 1239 (2021). He contends in his amended § 2255

motion that he “was not thoroughly clear with this issue in his prior motion.” Am. § 2255 Mot.

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2 (Doc. 11). It is true that in his original motion, he asserted that his counsel was ineffective

when he “didn’t object to prior convictions being established.” § 2255 Mot. 5 (Doc. 1).

Not only was Jackson “not clear” in articulating his categorical approach argument, he

did not even hint at it in his original motion. The process for “establishing” a prior conviction is

set forth in § 851 (“Proceedings to establish prior convictions”), which provides a defendant an

opportunity to object to its establishment:

(b) Affirmation or denial of previous conviction

If the United States attorney files an information under this section, the court shall

after conviction but before pronouncement of sentence inquire of the person with

respect to whom the information was filed whether he affirms or denies that he

has been previously convicted as alleged in the information, and shall inform him

that any challenge to a prior conviction which is not made before sentence is

imposed may not thereafter be raised to attack the sentence.

(c) Denial; written response; hearing

(1) If the person denies any allegation of the information of prior

conviction, or claims that any conviction alleged is invalid, he shall file a

written response to the information. A copy of the response shall be

served upon the United States attorney. The court shall hold a hearing to

determine any issues raised by the response which would except the

person from increased punishment. The failure of the United States

attorney to include in the information the complete criminal record of the

person or any facts in addition to the convictions to be relied upon shall

not constitute grounds for invalidating the notice given in the information

required by subsection (a)(1). The hearing shall be before the court

without a jury and either party may introduce evidence. Except as

otherwise provided in paragraph (2) of this subsection, the United States

attorney shall have the burden of proof beyond a reasonable doubt on any

issue of fact. At the request of either party, the court shall enter findings

of fact and conclusions of law.

(2) A person claiming that a conviction alleged in the information was

obtained in violation of the Constitution of the United States shall set forth

his claim, and the factual basis therefor, with particularity in his response

to the information. The person shall have the burden of proof by a

preponderance of the evidence on any issue of fact raised by the response.

Any challenge to a prior conviction, not raised by response to the

information before an increased sentence is imposed in reliance thereon,

shall be waived unless good cause be shown for failure to make a timely

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challenge.

21 U.S.C. § 851.

A common-sense reading of an accusation that counsel “didn’t object to prior convictions

being established” is that counsel failed to make the objections described in § 851(b) and (c). It

does not encompass—or arise out of a common core of operative facts as—an argument about

the legal effect of established prior convictions. Jackson makes this argument too late, so the

Court rejects it as a ground for § 2255 relief.

b. Amendment Claim 2

The second claim in Jackson’s amended § 2255 motion is that his counsel was

constitutionally ineffective for stating to the jury in the closing argument that Jackson was “not

innocent.” The transcript of counsel’s closing reveals that, after acknowledging Jackson was a

convicted felon, counsel said:

I am not saying that my client is innocent of everything. No, I’m not.

Like I said, I’m not trying to pull the wool over your eyes. I’m not trying to do

any of that murky water business he’s [the prosecutor’s] talking about.

I’m saying that he’s not guilty. The Government hasn’t proved beyond a

reasonable doubt. That’s what I’m saying.

* * *

Like I say, I’m not saying he’s innocent. I’m saying the Government has

not proved beyond a reasonable doubt that he’s guilty.

Trial Tr. 579-80 (Case No. 17-cr-40052-JPG, Doc. 127).

Nothing in Jackson’s original motion is based on the same core of operative facts as this

argument is—the statements in counsel’s closing argument as set forth above.1 Therefore,

1 Jackson’s original § 2255 motion complained of his counsel’s making stipulations without his

knowledge, consent, or permission. However, Jackson is clear in his motion that those

stipulations were that counsel would not use the criminal history of the CS, not that Jackson was

“not innocent.”

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Amendment Claim 2 does not relate back to Jackson’s original § 2255 motion, and the Court

rejects it as untimely.

c. Amendment Claim 3

The third claim in Jackson’s amended § 2255 motion is that his counsel was

constitutionally ineffective in his efforts to seek suppression of the evidence found in a search of

his home conducted on March 16, 2017. This claim arises out of some of the same operative

facts as part of Ground 1 of Jackson’s original § 2255 motion, which claims counsel was

constitutionally ineffective for failing to file a motion “properly,” failing to demand a hearing on

the motion, and failing to object to the order denying the motion. While the factual allegations

in the original petition are vague, liberally construing Jackson’s filings, the Court finds

Amendment Claim 3 relates back to Ground 1 of the original § 2255 motion.

B. Grounds Timely Alleged

1. Ineffective Assistance of Counsel

Ground 1 of Jackson’s original § 2255 motion and Amendment Claim 3 allege claims of

ineffective assistance of counsel. The Sixth Amendment to the Constitution provides that “[i]n

all criminal prosecutions, the accused shall enjoy the right . . . to have the Assistance of Counsel

for his defence.” U.S. Const. amend. VI. This right to assistance of counsel encompasses the

right to effective assistance of counsel. McMann v. Richardson, 397 U.S. 759, 771, n. 14

(1970); Watson v. Anglin, 560 F.3d 687, 690 (7th Cir. 2009).

A party claiming ineffective assistance of counsel bears the burden of showing (1) that

his counsel’s performance fell below objective standards for reasonably effective representation

and (2) that this deficiency prejudiced the defense. Strickland v. Washington, 466 U.S. 668,

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688-94 (1984); Groves v. United States, 755 F.3d 588, 591 (7th Cir. 2014). To satisfy the first

prong of the Strickland test, the petitioner must direct the Court to specific acts or omissions of

his counsel. Wyatt v. United States, 574 F.3d 455, 458 (7th Cir. 2009). The Court must then

consider whether, in light of all of the circumstances, counsel’s performance was outside the

wide range of professionally competent assistance. Id. To satisfy the second prong of the

Strickland test, the petitioner “must demonstrate ‘a reasonable probability that, but for counsel’s

unprofessional errors, the result of the proceeding would have been different. A reasonable

probability is a probability sufficient to undermine confidence in the outcome.’” Harrington v.

Richter, 562 U.S. 86, 104 (2011) (quoting Strickland, 466 U.S. at 694); accord Groves, 755 F.3d

at 591.

Jackson alleges a hodgepodge of instances of ineffectiveness, many too vague for the

Court to fully understand his argument. The Court will briefly address each in turn, but only

after observing the general rule that when a petitioner alleges his counsel was constitutionally

ineffective for failing to do a proper investigation, file motions, make arguments, or raise issues,

he must specify the things counsel would have found in a competent investigation or could have

said in a motion or argument, and he must explain how the omitted evidence or argument would

have had a reasonable chance of changing the result of the proceedings. See Long v. United

States, 847 F.3d 916, 920 (7th Cir. 2017) (petitioner must point to what an investigation would

have produced); Hardamon v. United States, 319 F.3d 943, 951 (7th Cir. 2003) (petitioner must

make a comprehensive showing as to what an adequate investigation would have produced);

Fuller v. United States, 398 F.3d 644, 652 (7th Cir. 2005) (petitioner must point to evidence or

meritorious argument counsel could have presented that would have created a reasonable

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probability that the result of the proceedings would have been different). Jackson fails to do this

in a number of his specific allegations of ineffective assistance of counsel in Ground 1 and

Amendment Claim 3:

• Jackson claims his counsel failed to file a motion to suppress properly and failed to assert

the search violated his Fourth Amendment rights. Counsel did, in fact, invoke Jackson’s

Fourth Amendment rights in the motion based in part on law enforcement’s failure to

have probable cause and failure to follow state law regarding overhears. However,

Jackson does not assert what argument or evidence counsel could have presented

differently in the motion that would have had a reasonable chance of convincing the

Court to grant the motion and suppress evidence.

• Jackson faults his counsel for failing to demand a hearing on the motion to suppress and

for failing to object to the order denying the motion. Counsel did, indeed, request a

hearing, but the Court denied that request, and Jackson has not specified what counsel

could have said that might have changed the Court’s mind. The Court decided the

motion on the papers, accepting all Jackson’s well-pled factual allegations as true.

However, there was no need for a hearing because the well-pled facts did not establish a

prima facie showing of illegality in the search, although a post-search technicality

rendered the evidence inadmissible in state court. Nor has Jackson pointed to anything

counsel could have presented at a hearing that would have had a reasonable probability of

convincing the Court to grant the motion under federal suppression standards.

Additionally, Jackson has not suggested what counsel might have said in response to the

order denying his motion to suppress that would have had a reasonable probability of

causing the Court to reverse its decision.

• Jackson faults his counsel for failing to file post-trial motions, and in correspondence he

allegedly sent to Jackson he lists a number of topics he wanted counsel to address in such

motions—motion to suppress, Fourth Amendment violations, Sixth Amendment

violations, lack of probable cause for the search, challenges to the search warrant, and

illegal eavesdropping (Doc. 11 at 33), as well as other topics raised at sentencing (Case

No. 17-cr-40052-JPG, Doc. 158). Even with respect to those topics, though, Jackson

does not suggest what arguments competent counsel should have made in a post-trial

motion and how they would have benefitted his case. In the amendment to his petition,

he suggests counsel should have filed a motion under Federal Rule of Criminal Procedure

35(a) to correct a “clear error,” but the issues of which Jackson complains to not amount

to the kind of errors correctible under this rule. Thus, he has not demonstrated he was

prejudiced by counsel’s failing to file post-trial motions.

• Jackson faults counsel for failing to move to dismiss the indictment based on defects and

grand jury violations, but he does not suggest the nature of the defects and violations or

how they rendered the indictment subject to dismissal. Without pointing to the specific

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arguments competent counsel could have used to seek dismissal of the indictment that

would have created a reasonable chance the Court would actually have accepted those

arguments, Jackson cannot show counsel was ineffective in this regard.

• Jackson faults counsel for failing to object to his guideline offense level enhancements—

possession of a firearm pursuant to U.S.S.G. § 2D1.1(b)(1); directing the use of violence

pursuant to U.S.S.G. § 2D1.1(b)(2); maintaining a residence for drug distribution

pursuant to U.S.S.G. § 2D1.1(b)(12); and obstruction of justice pursuant to U.S.S.G.

§ 3C1.1. Counsel did object to these enhancements in the objections to the PSR, and

Jackson has not specified what he could have said differently that would have had a

reasonable chance of changing the outcome of the sentencing proceeding.

• Jackson faults counsel for failing to object to the establishment of the prior state

convictions used to determine his criminal history category and increase his statutory

sentencing range. Jackson has not pointed to any evidence showing the convictions

listed in the PSR or the § 851 information were inaccurate, were not his, or were

otherwise subject to objection under 21 U.S.C. § 851(b) and (c). Thus, he has not

established what evidence or argument competent counsel could have presented to cause

the Court to find those convictions did not, in fact, exist or were not, in fact, his

convictions.

In other allegations of ineffective assistance of counsel, Jackson argues that counsel

should not have stipulated that he would not use the criminal history of the CS who conducted

the controlled buys upon which the search warrant was based to impeach the CS at trial.

Counsel apparently did this when he believed the Government would call the CS as a witness.

The Government ended up not calling the CS to testify, so counsel’s agreement about limiting

impeaching evidence was immaterial to the trial. Jackson suffered no prejudice from counsel’s

stipulation.

Jackson faults counsel for failing to object to a violation of Title III, the federal

eavesdropping statute, with respect to recordings of the three controlled buys in March 2017.

Law enforcement used those overhears and recorded information to seek the search warrant for

the March 16, 2017, search of Jackson’s home. The recordings were properly authorized by the

Saline County State’s Attorney, as explained in the Court’s denial of Jackson’s motion to

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suppress, although the failure to follow technical requirements rendered them inadmissible in

state court (Case No. 17-cr-40052-JPG, Doc. 84). Those recording, however, did not violate

Title III, which permits a person acting under color of law (such as a confidential informant

working for law enforcement) to intercept and record an oral communication of a conversation in

which the person is a party. 18 U.S.C. § 2511(2)(c). Nor, as the Court explained in its

suppression order, did the admission of those recordings violate any other federal law or the

Constitution. The recordings of the communications between the CS and Jackson that formed

the basis for the search warrant request did not violate Title III. Any objection to the use of the

recordings as in violation of Title III would have been meritless and would have been—as is

clear in the Court’s denial of Jackson’s motion to suppress—rejected by Court. Counsel was

not deficient for failing to make a frivolous argument, and Jackson suffered no prejudice as a

result.

Jackson complains that counsel failed to give him an opportunity to review the brief filed

in his direct appeal and failed to keep Jackson apprised of the outcome of the appeal. It is true

counsel has an obligation to “keep the defendant informed of important developments in the

course of the prosecution.” Strickland, 466 U.S. at 688. However, counsel that fails to

communicate is not constitutionally ineffective unless that failure causes some prejudice. Id. at

687. Here, even if counsel’s failure to show Jackson the appellate brief before he filed it could

be construed as short of adequate performance, Jackson has not explained how the brief could

have been made compelling enough to cause the Court of Appeals to reverse his sentence.

Appellate counsel is not deficient for failing to “raise every non-frivolous issue under the sun.”

Mason v. Hanks, 97 F.3d 887, 893 (7th Cir.1996). Counsel is only deficient if he “fails to

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appeal an issue that is both obvious and clearly stronger than one that was raised.” Winters v.

Miller, 274 F.3d 1161, 1167 (7th Cir. 2001); accord Makiel v. Butler, 782 F.3d 882, 898 (7th Cir.

2015); Suggs v. United States, 513 F.3d 675, 678 (7th Cir. 2008). Furthermore, a petitioner can

show prejudice from this deficiency only by demonstrating “that there is a reasonable probability

that, but for the deficient performance of his attorney, the result of the appeal would have been

different.” Suggs, 513 F.3d at 678. Jackson has pointed to no argument that is obvious and

clearly stronger than the ones that his counsel raised and that would have had a reasonable

probability of changing the result of the appeal.

Counsel’s failure to notify Jackson in a timely manner (which the Court accepts as true

for the purposes of this motion) of the disposition of his appeal meant that Jackson did not file a

timely motion for a rehearing before the Court of Appeals or petition for a writ of certiorari from

the Supreme Court. But Jackson has not pointed to any argument that could have been made in

those proceedings that would have had a reasonable chance of changing the result of his case.

The Court of Appeals had already rejected the arguments counsel made, and nothing suggests a

rehearing would have reached a different result. As for reaching the Supreme Court, even

having the case accepted was a long shot, and nothing suggests there was any issue the Supreme

Court would have relied on to reverse his sentence.2 As for Jackson’s delay in filing a timely

§ 2255 motion, Jackson has suffered no prejudice because the Court has accepted as timely his

2 To the extent Jackson may fault counsel for not filing a petition for a writ of certiorari based on

his earlier request, counsel had no duty to comply with that request. “[T]here is no

constitutional right to counsel at public expense when asking the Supreme Court for a writ of

certiorari.” United States v. Blake, 986 F.3d 756, 758 (7th Cir. 2021). The potentially

prejudicial delay would come from Jackson’s inability to file his own timely pro se petition but,

as noted in the body of this order, Jackson has not offered any argument the Supreme Court had

a reasonable chance of accepting.

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March 29, 2021, original motion. He has simply pointed to no prejudice from counsel’s failure

to timely notify him of the disposition of his appeal.

One final note about counsel’s performance is warranted. The Court judges counsel’s

performance as a whole rather than in isolated instances of alleged errors. Groves v. United

States, 755 F.3d 588, 593 (7th Cir. 2014). After carefully reviewing the record as a whole and

in light of the evidence in the case, the Court finds that there is no reasonable probability that,

but for the alleged errors of counsel in this case, even if considered in combination, the result of

the proceedings would have been different. Jackson presented a situation no lawyer likes to

face: strong evidence against a client for multiple crimes, one of which would expose him to a

mandatory life sentence. Counsel competently pursued reasonable avenues to reduce the risk to

Jackson, from filing motions, exploring plea negotiations, performing valiantly at trial (leading

to a hung jury on two counts), making reasonable objections at sentencing, and pursuing

competently-chosen arguments on appeal. That his efforts did not succeed does not mean they

were deficient. On the contrary, counsel acted well within the range of reasonably competent

performance.

2. Procedural Default

A § 2255 motion does not substitute for a direct appeal. Generally, a petitioner cannot

raise a claim for the first time in a § 2255 motion where he could have but failed to raise it on

direct appeal. White v. United States, 8 F.4th 547, 554 (7th Cir. 2021) (citing McCoy v. United

States, 815 F.3d 292, 295 (7th Cir. 2016)). A petitioner can overcome this procedural default

for constitutional claims if he can show cause for the default and prejudice from it or that he is

actually innocent of the crime. White, 8 F.4th at 554 (citing Bousley v. United States, 523 U.S.

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614, 622 (1998)). Not so for nonconstitutional claims, which cannot be raised in a § 2255

motion regardless of cause or prejudice. See Barnickel v. United States, 113 F.3d 704, 706 (7th

Cir. 1997) (“Nonconstitutional claims . . . which could have been raised on direct appeal but

were not, are deemed waived even without taking cause and prejudice into account.”).

And just as a § 2255 motion is not a substitute for a direct appeal, it is not a second

chance where a direct appeal was unsuccessful. A petitioner cannot raise an issue in a § 2255

motion that he already raised on direct appeal unless he can show changed circumstances.

Varela v. United States, 481 F.3d 932, 935 (7th Cir. 2007); Belford v. United States, 975 F.2d

310, 313 (7th Cir. 1992).

a. Hearing on Motion to Suppress

The only assertion left in Ground 2 after the Court’s preliminary screening order is that

Jackson’s due process rights were violated because the Court refused to hold a hearing on the

motion to suppress. As a preliminary matter, Jackson has procedurally defaulted on this claim.

The failure to provide a hearing on a motion to suppress is an issue that could have been raised

on direct appeal.

On direct appeal, Jackson did not raise a due process claim regarding the Court’s failure

to hold a hearing on his motion to suppress, and he has not shown cause or prejudice now. And

while ineffective assistance of counsel can constitute cause for failing to raise an issue on direct

appeal, appellate counsel was not deficient in this case. The issues he raised on appeal were

reasonable, and the Court’s failure to hold a hearing was not an obvious issue that was clearly

stronger than the ones raised. As explained above, the Court afforded Jackson an opportunity to

be heard, albeit on paper, and decided the motion viewing all well-pled fact in his favor.

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Declining to hold a hearing did not prejudice Jackson. Because he has procedurally defaulted

on Ground 2 of his original § 2255 motion, he is not entitled to § 2255 relief.

b. Collusion between Federal and State Officials

In Ground 3, Jackson alleges the nonconstitutional claim that there was something

improper about the interactions, which he characterizes as collusion, between state and federal

law enforcement officials in investigating his activity and bringing his criminal case. He

believes there is something wrong with state officers’ conducting an investigation without

federal assistance, and then federal officials’ prosecuting the case that resulted from the

investigation conducted solely by state officials, including the use of evidence that would be

inadmissible under state law but not federal law.

The circumstances on which Jackson’s claim is based were fully reflected in the criminal

case record, including but not limited to the briefing on his motion to suppress and the

Government’s motion in limine. Jackson could have raised this issue on direct appeal, but he

did not. Consequently, he cannot raise the claim now in his § 2255 motion.

To the extent Jackson may suggest this is a constitutional issue, he has not shown cause

or prejudice. Specifically, he has pointed to no law indicating the conduct of the state and

federal participants in this case was wrongful. Counsel was not deficient for failing to raise the

issue on direct appeal in favor of the stronger arguments he did raise, and Jackson suffered no

prejudice from that decision.

c. Denial of Motion to Suppress

In Ground 4, Jackson asks the Court to revisit its denial of his motion to suppress.

Again, this could have been raised on direct appeal but was not. Jackson has not shown that this

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issue was obvious and clearly stronger than the arguments that were raised. Indeed, he had a

full and fair opportunity to litigate his Fourth Amendment claim at the trial court level. Owens

v. United States, 387 F.3d 607, 609 (7th Cir. 2004) (citing Stone v. Powell, 428 U.S. 465 (1976).

And as set forth in the Court’s discussion of his first ineffective assistance of counsel argument

above, Jackson has not shown, even now, that there was any Fourth Amendment violation that

would have justified suppressing evidence found in the search or as the “fruit of the poisonous

tree.” In the absence of cause and prejudice, Jackson cannot raise this issue in his § 2255

motion.

IV. Certificate of Appealability

Pursuant to Rule 11(a) of the Rules Governing § 2255 Proceedings and Rule 22(b)(1) of

the Federal Rules of Appellate Procedure, the Court considers whether to issue a certificate of

appealability of this final order adverse to the petitioner. A certificate of appealability may

issue “only if the applicant has made a substantial showing of the denial of a constitutional

right.” 28 U.S.C. § 2253(c)(2); see Tennard v. Dretke, 542 U.S. 274, 282 (2004); Ouska v.

Cahill-Masching, 246 F.3d 1036, 1045 (7th Cir. 2001). To make such a showing where the

Court denies relief on procedural grounds, the petitioner must show “that jurists of reason would

find it debatable whether the petition states a valid claim of the denial of a constitutional right

and that jurists of reason would find it debatable whether the district court was correct in its

procedural ruling.” Slack v. McDaniel, 529 U.S. 473, 484 (2000) (emphasis added); accord

Gonzalez v. Thaler, 565 U.S. 134, 140-41 (2012). Thus, disputes about procedural or statutory

issues in a case cannot justify a certificate of appealability unless “a substantial constitutional

issue lurks in the background, and the statutory question is independently substantial.”

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Ramunno v. United States, 264 F.3d 723, 725 (7th Cir. 2001) (question of a petition’s timeliness)

(citing Slack, 529 U.S. at 483-85).

The Court finds that Jackson has made an adequate showing to warrant a certificate of

appealability on the following questions:

• The procedural question of whether Jackson’s Amendment Claim 1, deemed filed

January 5, 2022, relates back to Jackson’s original § 2255 motion, deemed filed March

29, 2021, and,

• The substantial constitutional question lurking in the background of whether Jackson has

stated a valid claim for denial of his Sixth Amendment right to effective assistance of

counsel because, at sentencing in November 2018, his trial counsel did not challenge

whether Jackson’s prior state drug convictions charged in the § 851 information

supported enhanced sentencing ranges under 21 U.S.C. § 841(b)(1) after United States v.

Elder, 900 F.3d 491 (7th Cir. 2018), and Lorenzo v. Sessions, 902 F.3d 930 (9th Cir.

2018), but before United States v. De La Torre, 940 F.3d 938, 948 (7th Cir. 2019), and

United States v. Ruth, 966 F.3d 642 (7th Cir. 2020), cert. denied, 141 S. Ct. 1239 (2021).

The Court will deny a certificate of appealability as to all other issues raised in this case.

V. Conclusion

For the foregoing reasons, the Court:

• DENIES Jackson’s motion to vacate, set aside or correct his sentence pursuant to 28

U.S.C. § 2255 and its amendment (Docs. 1 & 11);

• ISSUES a certificate of appealability on the questions set forth in the prior section of this

order but DENIES a certificate of appealability in all other respects; and

• DIRECTS the Clerk of Court to enter judgment accordingly.

IT IS SO ORDERED.

DATED: December 19, 2022

s/ J. Phil Gilbert

J. PHIL GILBERT

DISTRICT JUDGE

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