Cherdak v. Cottone

UNITED STATES DISTRICT COURT

MIDDLE DISTRICT OF FLORIDA

FORT MYERS DIVISION

ERIK BENJAMIN CHERDAK,

Plaintiff,

v. Case No.: 2:22-cv-634-SPC-NPM

VINCENT PAUL COTTONE and

LINDA MARIE COTTONE,

Defendants.

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OPINION AND ORDER1

Before the Court is Defendants’ Motion to Declare Plaintiff a Vexatious

Litigant and for Related Injunctive Relief (Doc. 45), along with Plaintiff Erik

Cherdak’s Response. (Doc. 50). For the following reasons, the Court denies

Defendants’ Motion.

BACKGROUND

Last year, Cherdak filed a Complaint that alleged defamation per se,

defamation by implication, intentional infliction of emotional distress, and

conspiracy to harm under Florida law. (Doc. 1 at 17-38). These causes of action

1 Disclaimer: By using hyperlinks, the Court does not endorse, recommend, approve, or

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does not affect this Order.

arose from Defendants’ affidavits about Cherdak in connection with an ongoing

family court action in South Carolina.

Defendants filed a Renewed Motion to Dismiss (Doc. 13), which Cherdak

opposed (Doc. 16). The Court granted Defendants’ Renewed Motion to Dismiss,

dismissing all claims. (Doc. 35).

Now, Defendants move to declare Cherdak a vexatious litigant.

Defendants also ask to be excused from Local Rule 3.01(g) conferral with

Cherdak and to enjoin Cherdak from filing additional papers in this Court as

a pro se litigant without prior leave from this Court. Cherdak opposes this

motion’s merits and challenges the Court’s subject-matter jurisdiction over this

post-judgment motion. (Doc. 50).

LEGAL STANDARD

Federal courts have inherent authority “to protect their jurisdiction from

conduct which impairs their ability to carry out Article III functions.” Procup

v. Strickland, 792 F.2d 1069, 1073 (11th Cir. 1986) (citing In re Martin-

Trigona, 737 F.2d 1254, 1261-62 (2d Cir. 1984)). This authority was codified

by Congress in the All Writs Act, which does not create jurisdiction but does

give “all courts established by Act of Congress” the ability to issue “all writs

necessary or appropriate in aid of their respective jurisdictions and agreeable

to the usages and principles of law.” 28 U.S.C. § 1651 (1949). Through this

Act, federal courts may enjoin vexatious litigants from filing in judicial (and

nonjudicial) forums. See Riccard v. Prudential Ins. Co. of Am., 307 F.3d 1277

n.15 (11th Cir. 2002).

An injunction under the All Writs Act does not require the same

prerequisites as a traditional preliminary injunction. Klay v. United

Healthgroup, Inc., 376 F.3d 1092, 1100 (11th Cir. 2004) (“The requirements for

a traditional injunction do not apply to injunctions under the All Writs Act

because the historical scope of a court’s traditional power to protect its

jurisdiction, codified by the Act, is grounded in entirely separate concerns”).

For an injunction under the All Writs Act, “[a] history of litigation entailing

‘vexation, harassment and needless [. . .] burden on the courts and their

supporting personnel’ is enough.” Ray v. Lowder, No. 5:02-CV-316, 2003 WL

22384806, at *5 (M.D. Fla. Aug. 29, 2003) (quoting Martin-Trigona, 737 F.2d

at 1262). Five factors provide guidance in determining whether a litigant’s

conduct is vexatious enough to warrant an injunction:

(1) the litigant’s history of litigation and in particular

whether it entailed vexatious, harassing or duplicative

lawsuits; (2) the litigant’s motive in pursuing the

litigation, e.g. does the litigant have an objective good

faith expectation of prevailing; (3) whether the litigant

is represented by counsel; (4) whether the litigant has

caused needless expense to other parties or has posed

an unnecessary burden on the courts and their

personnel; [and] (5) whether other sanctions would be

adequate to protect the courts and other parties.

Ray, 2003 WL 22384806, at *8 (citing Safir v. United States Lines, Inc., 792

F.2d 19, 24 (2d Cir. 1986)).

DISCUSSION

Defendants move to declare Cherdak a vexatious litigant, arguing that

his conduct—both inside and outside of this Court—has been harassing and

frivolous. In opposition, Cherdak argues that the motion is improper for the

Court to consider post-judgment and that it lacks merit.

The Court begins with the threshold issue—jurisdiction.

A. Subject-Matter Jurisdiction

Cherdak argues that, upon dismissing the case with prejudice, the

Court’s subject-matter jurisdiction terminated pursuant to “28 U.S.C.” (Doc.

50 at 9). In short, Cherdak argues that only Fed. R. Civ. P. 59 and 60 motions

can be brought in an action post-judgment. (Doc. 50 at 9). And since

Defendants do not move under Rule 59 or 60 to have Cherdak declared a

vexatious litigant, he believes the Court cannot entertain the Motion. He is

incorrect.

A motion to have a litigant declared vexatious is akin to a motion for

sanctions, which may be heard post-judgment. See Thompson 2010 WL

5497673, at *11; Byrne v. Nezhat, 261 F.3d 1075, 1105-1106 (11th Cir. 2001)

(discussing the “three sources of authority” to impose sanctions—Fed. R. Civ.

P. 11, 28 U.S.C. § 1927, and “the court’s inherent power”). Motions for

sanctions are reviewable post-judgment in part because they address collateral

issues that have no bearing on the Court’s final verdict on the merits. See

Cooter & Gell v. Hartmarx Corp., 496 U.S. 384, 396 (1990), superseded in part

by Fed. R. Civ. P. 11 (1993).

Similarly, Defendants’ vexatious litigant motion addresses a collateral

issue—the burden Cherdak has and will impose on Defendants and the Court.

But while collateral, this issue is important to docket management and the

smooth flow of the Court’s cases.

The Court has inherent authority to protect its docket from potential

abuses which could stymie the Court’s ability to carry out its Article III

functions. See Procup, 792 F.2d at 1073-74. If the Court had no jurisdiction

over post-judgment vexatious litigant motions, the Court would be helpless in

the face of vexatious post-judgment filings. This does not comport with logic

or the law. See Thompson, 2010 WL 5497673, at *24 (explaining that a motion

for injunctive relief against a vexatious litigant after the plaintiff voluntarily

withdrew the case is a collateral issue that the court can address); see also

Qureshi v. United States, 600 F.3d 523 (5th Cir. 2010). Whether this Motion

to Declare Plaintiff a Vexatious Litigant was filed before or after the dismissal

of this case, the Court maintains authority to decide it.

B. Vexatious Litigant

Since the Court has jurisdiction to decide Defendants’ motion, the Court

now addresses whether Cherdak’s conduct is so vexatious it warrants an

injunction.

1. Cherdak’s History of Litigation

Defendants assert that Cherdak has shown vexatious conduct through

his history of litigation, both in this Court and in other courts. (Doc. 45 at 7).

Cherdak’s concerning conduct began in 2015 with the case of Fitistics,

LLC v. Cherdak, No. 1:16-cv-112-LO-JFA, 2018 WL 4059375 (E.D. Va. Aug. 23,

2018), presided over by Judge Liam O’Grady. (Doc. 45-1 at 5-6). Fitistics,

LLC—a former client of Cherdak when he was a practicing attorney—sued him

for breach of contract, breach of fiduciary duty, conversion, and fraud. Fitistics,

LLC, 2018 WL 4059375, at *2. During the bench trial, Judge O’Grady made

several observations about Cherdak’s conduct in the case:

[T]he Court finds it necessary to comment on

[Cherdak’s] testimony. The Court found Cherdak’s

testimony to be wholly incredible, regularly

contradicted by common sense and plain evidence

before the Court . . . The Court is also convinced that

Cherdak lied to United States Magistrate Judge

Judith Dein in the District of Massachusetts on

October 1, 2015 at an in-person hearing . . . There is

also no doubt that Cherdak perjured himself in this

case . . . His character for untruthfulness, prior false

statements to a federal judge, perjury in filings with

the United States Bankruptcy Court, and perjury

during his deposition and during the trial in this

matter render his testimony worthless to the Court.

Fitistics, LLC, 2018 WL 4059375, at *5-6.2

2 Judge O’Grady also credited the testimony of Steven Ward, an attorney who had “received

bad checks from Cherdak.” Fitistics, LLC, 2018 WL 4059375, at *5. Mr. Ward testified that

“I don’t think [Cherdak] has any truthfulness. I mean, frankly, if he told me it was raining

outside, I’d have to go check to see if it was before I got my raincoat.” Id.

By separate order, Judge O’Grady found Cherdak’s conduct

sanctionable, noting that his “brazen conduct in filing many frivolous pleadings

and putting false information before the Court demonstrates both the severity

of the Rule 11 violation and the importance of a significant sanction to serve as

deterrence from Mr. Cherdak continuing to abuse the legal system.” Fitistics,

LLC v. Cherdak, No. 1:16-cv-112-LO-JFA, 2019 WL 7899995, at *2 (E.D. Va.

June 10, 2019) (emphasis added).

Cherdak responded to his loss in the Fitistics case by suing Judge

O’Grady and Judge O’Grady’s judicial assistant via a 72-page complaint. (Doc.

45-1 at 21); Cherdak v. O’Grady, No. 21-CV-0141, 2022 WL 599487 (E.D. Va.

Feb. 28, 2022). Cherdak’s claims were dismissed with prejudice. Id. at *10.

Cherdak’s legal troubles did not stop there. In October 2022, Cherdak

was disbarred from the practice of law in Pennsylvania. (Doc. 45-1 at 1). In a

lengthy report and recommendation, the Disciplinary Board of the Supreme

Court of Pennsylvania concluded that Cherdak’s behavior during his

disciplinary proceedings “evidenced a lack of respect for the disciplinary

system.” (Doc. 45-1 at 31). The Board also noted that Cherdak’s suit against

Judge O’Grady showed his reluctance to accept the outcome of the Fitistics case

and that Cherdak had wasted an opportunity for self-advocacy on

“attempt[ing] to relitigate previous rulings and attack[ing] perceived wrongs

brought upon him, specifically by Judge O’Grady.” (Doc. 45-1 at 30, 32).

Then Cherdak became involved in family court litigation in South

Carolina. In the family court matter, he filed an “Emergency Motion for an

Order Enjoining Attorney Jonathan E.B. Lewis from Engaging in Untruthful,

Threatening, and Harassing Conduct.” (Doc. 45-5). Cherdak used this

“emergency” motion as a 50-page opportunity to complain about opposing

counsel. (Doc. 45-5). In this family court matter, he also filed a lengthy (12-

page) brief to strike an affidavit over the misspelling of an address (“150 Wappo

Creek Drive” as opposed to “150 Wappoo Creek Drive”) and the absence of an

apartment number. (Doc. 45-3).

Cherdak’s conduct in prior litigation reflects the tenor of his conduct

before this Court, where he has engaged in attacks on opposing counsel and

filed unnecessary and lengthy papers. Cherdak began this case with a 46-page

meandering Complaint which contained—among other things—a 1.5-page

footnote on “parental alienation.” (Doc. 1 at n.4). He then filed an emergency

motion on a matter that was not, in fact, an emergency. (Doc. 3). As the case

progressed, he filed several objectively unnecessary documents, such as an

Objection to Defendant’s Notice of Allegedly Related Cases and Motion to

Strike that Notice in Accordance with the Court’s Inherent Authority (Doc. 22)

and an Objection to Defendants’ Supplemental Rule 3.01(g) Certification at

ECF 48 on the Basis of False Representations Made by Lead Defense Counsel

Hazzard in that Supplemental Certification (Doc. 49).

Cherdak’s history of litigation is certainly “vexatious” in the typical

dictionary definition of the word. He has been demonstrably disrespectful in

court and disciplinary proceedings, and he has filed unnecessary papers. Yet

his history of litigation is not yet to a level that warrants an injunction. So

this factor does not support entering injunctive relief against Cherdak.

2. Cherdak’s Motive in Pursuing Litigation

Cherdak’s motive in pursuing this case can be gleaned from two things:

(1) the lack of an objective, good faith basis of prevailing on the claims raised,

and (2) his conduct in past litigation.

In the Complaint, Cherdak raised two claims of defamation, an

intentional infliction of emotional distress claim, and a civil conspiracy claim.

(Doc. 1). At minimum, his claims of intentional infliction of emotional distress

and civil conspiracy are objectively frivolous to someone with a basic

understanding of the law. Cherdak—as a former attorney—has more than a

basic understanding of the law. Yet Cherdak reframed a defamation claim as

intentional infliction of emotional distress and brought a civil conspiracy claim

with no underlying tort. Cherdak practiced as a licensed attorney for about

thirty years. Someone with an expansive legal background, like him, would

have no objective, good faith expectation of prevailing on either of these

claims.3

But it seems that Cherdak was more concerned with bullying

Defendants than with success on the merits. His bullying behavior may have

been intended to intimidate Defendants into not providing testimony (via

affidavit or otherwise) in the family court proceedings in South Carolina. See,

e.g., Doc. 45-1 at 32 (the Disciplinary Board of the Supreme Court of

Pennsylvania noting that Cherdak’s “usual way of doing business . . . appears

to be to attempt to manipulate, confuse, embarrass, and bully those with whom

he is dealing”). Or it may simply have been intended as an outlet for Cherdak

to vent his frustrations with his in-laws. See, e.g., Doc. 35 at 7 (the Court

discussing Cherdak’s Complaint and reminding him that “the Complaint need

not describe all the misdeeds of Cherdak’s family members nor how Cherdak

feels those family members have wronged him”). Or it may have been an effort

to get money to assuage his millions in outstanding debt. (Doc. 45-1 at 21). All

of these reasons find support in the record. Regardless, his motive in pursuing

litigation was not in good faith.

3 Cherdak advised defense counsel to “think three times before you file” and ask herself three

questions: “[D]id I get the law right? [D]id I get the facts right? [A]nd am I proceeding with

good faith that what I intend to file in a court of law is a good application of true controlling

law to the real facts?” (Doc. 50-2 at 3). Cherdak did not consider these questions in his filings

in this case and is cautioned to consider them before filing any additional papers with this

Court.

Cherdak’s leading concern—bullying—is shown by the time and effort he

has spent attacking defense counsel and Defendants. Cherdak has repeatedly

accused defense counsel of intentionally misleading the Court. (Doc. 45 at 2;

Doc. 16 at n.1, 11, 12, 13, n.4, 16; Doc. 50 at 1-2). He has variously alleged that

defense counsel’s “advocacy knows no bounds of truth,” that defense counsel

“has lied to a court, [and] has engaged in heinous conduct,” and that defense

counsel has committed malpractice. (Doc. 50 at 8; Doc. 55 at 11).

And when Defendants moved to declare Cherdak a vexatious litigant

(Doc. 45), Cherdak’s first action—even before filing a response to the motion—

was to send an email directing defense counsel to “TAKE IMMEDIATE

ACTION TO WITHDRAW MOTION.” (Doc. 50-1). In the email, he told

defense counsel “you have misguided your clients, your firm, and yourself into

sanctions territory.” (Doc. 50-1 at 3). Cherdak copied who he viewed as senior

personnel at defense counsel’s law firm: “I’ve sent this email to your firm’s

principals . . . so they are made aware of your actions to date and so they are

fully apprised of the actions of you and your firm . . . they should know that

their firm is now subject to claim(s) under Florida law.” (Doc. 50-1 at 4).

Cherdak threatened to “seek sanctions” and “make a claim for abuse of process

under Florida law” if defense counsel did not withdraw the motion within three

hours of the time of his email. (Doc. 50-1 at 3).

Cherdak’s bullying has also been aimed directly at his Defendant in-

laws. They are the named parties, they are the ones expending money on

counsel—and they are also the ones who authored affidavits against Cherdak

in ongoing family court proceedings in South Carolina. Cherdak has

deliberately considered the impact this lawsuit will have on them, noting in an

email to defense counsel that “it will be interesting to see how your clients

handle having to call witnesses (including all of their grandchildren) to the

stand and be subjected to vigorous cross examination.” (Doc. 50-2 at 2).

Overall, his conduct reflects motives that are consistent with the

observations of the Disciplinary Board of the Supreme Court of Pennsylvania—

that Cherdak’s “usual way of doing business . . . appears to be to attempt to

manipulate, confuse, embarrass, and bully those with whom he is dealing.”

(Doc. 45-1 at 32). Whether this case was brought to bully his Defendant in-

laws, to preclude unfavorable affidavits from being used against him in family

court, or to try to recoup some of the $2.3 million debt he has outstanding (Doc.

45-1 at 21), one thing seems clear—Cherdak’s motives in bringing his claims

were improper. And improper motives weigh in favor of injunctive relief.

3. Whether Cherdak is Represented by Counsel

Cherdak is representing himself pro se. Generally, the courts give great

discretion to pro se litigators due to their presumed inexperience and lack of

knowledge of the legal system. See Erickson v. Pardus, 551 U.S. 89, 94 (2007).

But Cherdak is a former attorney, is familiar with the law, and has shown his

knowledge and ability to research, understand, and apply the law. Judge

O’Grady concluded that “Cherdak is not entitled to the consideration normally

afforded to pro se parties who lack familiarity with the law, the court system,

and its policies and procedures.” Fitistics, LLC v. Cherdak, 2018 WL 4059375,

at *1. This Court agrees. So this factor supports entering injunctive relief.

4. Whether Cherdak has Unnecessarily Burdened Defendants and the Court

The fourth factor—whether a plaintiff’s conduct has unnecessarily

burdened the Court and the parties involved—is one of the most important in

determining whether a court should enter injunctive relief. Ray, 2003 WL

22384806, at *3.

Cherdak opened this case with a shotgun pleading, a paper which wastes

Defendants’ time by failing to adequately inform Defendants of the claims

against them and also wastes the Court’s time and resources. See Weiland v.

Palm Beach Cty. Sheriff’s Off., 792 F.3d 1313, 1323 (11th Cir. 2015). And this

shotgun pleading included claims that Cherdak knew lacked legal merit, which

forced Defendants to defend against obviously meritless claims and the Court

to expend resources to issue an Order on these claims.

Cherdak then filed an emergency motion for a non-emergent issue, which

also inappropriately burdened the Court’s resources—particularly when the

Court was still recovering from Hurricane Ian. (Doc. 3). And of course, his

conduct throughout litigation has been problematic—notably through his

unnecessary, voluminous, and rambling filings.

But his conduct in this case, when considered in its totality, has not yet

imposed a burden on Defendants or this Court sufficient to warrant an

injunction. This is Cherdak’s first lawsuit filed in the Middle District of

Florida, and the current volume and content of Cherdak’s filings—although

cumbersome and trying—fail to rise to the same level as other enjoined

plaintiffs in this District. See Ray, 2003 WL 22384806; Bernath, 2017 WL

3887785. This factor does not support the imposition of an injunction.

5. Whether Other Sanctions Would be Appropriate

Monetary sanctions can sometimes be sufficient to curb vexatious

conduct, but such sanctions are unlikely to deter Cherdak.

First, Cherdak is familiar with sanctions, having been sanctioned before

in Fitistics, LLC v. Cherdak, 2019 WL 7899995, in the amount of $361,576.18.

These sanctions have not curbed Cherdak’s behavior.

Second, Cherdak has a history of nonpayment and fraudulent payments.

(Doc. 45-1 at 19-20). As of August 29, 2022, Cherdak still owes more than $2.3

million in outstanding judgments. (Doc. 45-1 at 21). Cherdak’s financial

delinquency and outstanding debt suggests that it is doubtful any financial

sanction will sufficiently deter him from future vexatious filings. Thus, this

factor weighs in favor of entering injunctive relief.

This means that by raw score (three factors in favor of injunctive relief

and two factors against), this Court should declare Cherdak a vexatious

litigant. But the analysis is not so mechanical. Cherdak’s conduct is

undeniably problematic. But his conduct—while vexatious in the dictionary

sense—does not yet meet the “vexatious litigant” legal standard, and the Court

declines to impose an injunction.

A. Local Rule 3.01(g)

Defendants also request relief from compliance with Local Rule 3.01(g),

which requires a moving party to “confer with the opposing party in a good

faith effort to resolve the motion” before filing. Cherdak opposes Defendants’

request on the grounds that defense counsel “materially misrepresent[ed] the

facts surrounding Plaintiff’s good-faith in working to meaningfully participate

in a genuine and meaningful meet and confer conference.” (Doc. 50 at 19).

While the Court fully appreciates Defendants’ frustration, a blanket

exemption from compliance is not appropriate. The Court urges Cherdak to

keep his email correspondence and conferrals with defense counsel brief, polite,

and concise. “Concise” is defined as “free from all elaboration and superfluous

detail.” Concise, Merriam-Webster, https://www.merriam-webster.com/

dictionary/concise (last visited July 12, 2023) (emphasis added).

Accordingly, it is now

ORDERED:

Defendants’ Motion to Declare Plaintiff a Vexatious Litigant and for

Related Injunctive Relief (Doc. 45) is DENIED.

DONE and ORDERED in Fort Myers, Florida on July 18, 2028.

UNITED STATES DISTRICT JUDGE

Copies: All Parties of Record

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