Petition for Writ of Certiorari — Emmet O'Brien, Petitioner v. Paul Flick, et al.

APPENDIX

In the Supreme Court of the United States

Emmet O’Brien, Petitioner

v.

Paul Flick and Samuel Chamberlain, Respondents

On Petition for a Writ of Certiorari

to the United States Court of Appeals

for the Eleventh Circuit

TABLE OF CONTENTS TO THE APPENDIX

Appendix A - Omnibus Order on Pending Motions and Dismissing Case ............................................ App. 1

(S.D. Ha., Case No. 0:24-cv-61529-MD, ECF No. 22, Jan. 10,2025)

Appendix B - Opinion of the United States Court of Appeals for the Eleventh Circuit ....................... App. 18

(11th Cir., Case No. 25-10143-D, Sept. 25,2025)

Appendix C - Order Denying Petition for Panel Rehearing and Rehearing En Banc ...........................App. 24

(11th Cir., Case No. 25-10143-D, Nov. 25,2025)

Appendix D - Order Denying Defendant’s Motion for Leave to Amend Pleadings ............................. App 27

(AE Capital Group LLC v. No-H2O USA, Inc.,

S.D. Ha., Case No. 0:23-cv-60601-RS, ECF No. 77, Aug. 14,2024)

Appendix E-Order of Dismissal of Emmet O’Brien (Without Prejudice) ...................................... App 32

(AE Capital Group LLC v. No-H2O USA, Inc.,

S.D. Ha., Case No. 0:23-cv-60601-RS, ECF No. 97, Aug. 23,2024)

Appendix F - Order Denying Plaintiff’s Motion for Summary Judgment ........................................ App. 34

(AE Capital Group LLC v. No-H2O USA, Inc.,

S.D. Ha., Case No. 0:23-cv-60601-RS, ECF No. 58, July 12,2024)

Appendix G - Order of Dismissal (Without Prejudice) ...................................................................... App. 45

Piccadilly Holdings II, LLC v. No-H2O USA, Inc.

(S.D. Ha., Case No. 0:23-cv-60978-DSL, ECF No. 135, Jan. 5,2026)

Appendix H - Order Denying Second Motion for Summary Judgment ............................................ App. 51

Piccadilly Holdings II, LLC v. No-H2O USA, Inc.

(S.D. Ha., Case No. 0:23-cv-60978-DSL, ECF No. 114, Feb. 28,2025)

APPENDIX B

Opinion of the United States Court of Appeals for the Eleventh Circuit

(11th Cir., Case No. 25-10143-D, Sept. 25,2025)

Filed: September 25,2025

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NOT FOR PUBLICATION

the

Mnifrb JBfafes (Unnrt of Appeals

Star tye 'JEbtanty Circuit

No. 25-10143

Non-Argument Calendar

EMMET O'BRIEN,

Plaintiff-Appellant,

versus

PAUL FLICK,

SAMUEL CHAMBERLAIN,

Defendants- Appellees.

Appeal from the United States District Court

for the Southern District of Florida

D.C. Docket No. 0:24-cv-61529-MD

Before Newsom, Grant, and Black, Circuit Judges.

PER CURIAM:

Emmet O’Brien, proceeding pro se, appeals the district

court’s dismissal of his amended complaint with prejudice,

App. 19

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Opinion of the Court

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25-10143

contending the district court erred by finding his claims were com­

pulsory counterclaims that should have been raised in a prior law­

suit between the parties. He also contends the district court abused

its discretion by striking his motion for leave to file a sur-reply be­

cause he repeatedly failed to comply with the local rules. After re­

view,1 we affirm.

I. DISCUSSION

A. Compulsory Counterclaims

Rule 13(a) provides a party "must” state as a counterclaim

any claim that "arises out of the transaction or occurrence that is

the subject matter of the opposing party’s claim.” Fed. R. Civ. P.

13(a)(1)(A). “Compulsory counterclaims which are not brought

are thereafter barred.” Nippon Credit Bank, Ltd. v. Matthews, 291 E3d

738, 755 (11th Cir. 2002), abrogated on other grounds by Diamond Crys­

tal Brands, Inc. v. Food Movers Int'l, Inc., 593 F.3d 1249 (11th Cir. 2010).

"The requirement that counterclaims arising out of the

same transaction or occurrence as the opposing party's claim ‘shall’

be stated in the pleadings was designed to prevent multiplicity of

actions and to achieve resolution in a single lawsuit of all disputes

arising out of common matters.” S. Const. Co. v. Pickard, 371 U.S.

57, 60 (1962). Two claims arise out of the same transaction or

1 We review de novo the dismissal of a plaintiff s complaint because it should

have been presented as a compulsory counterclaim. See Montgomery Ward Dev.

Corp. v.Juster, 932 F.2d 1378,1379 (11th Cir. 1991). We review a district court’s

application of local rules for abuse of discretion. See Reese v. Herbert, 527 F.3d

1253, 1267-68 (11th Cir. 2008).

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3

occurrence when they bear a ‘logical relationship” to one another,

or, in other words, when "the same operative facts serve as the basis

of both claims.” Republic Health Corp. v. Lifemark Hosps, of Fla., Inc.,

755 F.2d 1453,1455 (11th Cir. 1985) (quotation marks omitted).

The district court did not err in determining that O’Brien’s

claims were compulsory counterclaims. They share a logical rela­

tionship with the claims made in the lawsuits brought against

O’Brien by the corporate entities of Paul Flick and Samuel Cham­

berlain.2 Those claims dealt with the unraveling business relation­

ship between No-H2O, O’Brien, Flick, and Chamberlain in Decem­

ber 2022. The deadline to raise counterclaims for these suits was

October 2023 and November 2023, respectively. Although O’Brien

describes some conduct of Flick and Chamberlain that allegedly

occurred after these deadlines, his claims focus on their conduct

internal to the No-H2O business and thus matured well before

these deadlines. O’Brien fails to rebut the district court’s finding

that the underlying facts were known or would have been known

to O’Brien through diligence before the counterclaim deadline.

Further, AE Capital’s voluntary dismissal of its claims against

O’Brien did not relieve him of his obligation to assert those claims

during this timeframe. See Nippon Credit Bank, Ltd., 291 F.3d at 755.

O’Brien’s remaining arguments are unavailing. First, the dis­

trict court in AE Capital did not permit him to separately file the

claims in the instant action. Instead, it stated that it "does not

2 AE Capital Group LLC v. No-H20 USA, Inc. , No. 023-cv-60601-RS (S.D. Fla.);

Piccadilly Holdings II, LLCv. No-H20 USA, Inc., No. 23-cv-60978-DSL (S.D. Fla.).

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decide whether O’Brien has valid, actionable claims.” Second, the

law does not support O’Brien’s distinction between business-re­

lated claims and personal harm claims. Third, O’Brien’s claim that

equitable estoppel applies to the conduct of Flick and Chamberlain

lacks support.

The district court did not err in dismissing O’Brien’s com­

plaint with prejudice because his claims share a logical relationship

with two prior suits filed against him and should have been raised

as counterclaims.3

B. Sur-Reply

Under Southern District of Florida Local Rule 7.1(a)(3), be­

fore filing a motion for leave to file a sur-reply, the moving party

“shall confer (orally or in writing), or make reasonable effort to

confer (orally or in writing), with all parties or non-parties who

may be affected by the relief sought in the motion in a good faith

effort to resolve by agreement the issues to be raised in the mo­

tion.” S.D. Fla. L.R. 7.1(a)(3). The opposing party “shall cooperate

and act in good faith in attempting to resolve the dispute.” Id. If

the parties are unable to resolve the dispute, the moving party must

include a certificate of conference with their motion, detailing the

efforts made to resolve the matter and the opposing party’s posi­

tion. Id.

3 Because O’Brien’s causes of action were compulsory counterclaims, we need

not address the arguments regarding the district court’s sanction of O’Brien

by dismissing his amended complaint.

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5

O’Brien fails to rebut the district court’s finding that he re­

peatedly violated the conferral requirements, failed to take respon­

sibility, and failed to declare his intent to comply moving forward.

He also fails to elaborate on his good-faith efforts to comply with

the conferral requirement, instead focusing on opposing counsel’s

alleged tactics. The district court did not abuse its discretion by

striking O’Brien’s motion.

II. CONCLUSION

The district court did not err in dismissing O’Brien’s com­

plaint with prejudice because his claims share a logical relationship

with two prior suits filed against him and should have been brought

as counterclaims. The district court also did not abuse its discretion

by striking his motion for leave to file a sur-reply because O’Brien

repeatedly failed to comply with conferral requirements, demon­

strated no remorse for failing to do so, and provided no indication

that he intended to comply moving forward.

AFFIRMED.

App. 23

APPENDIX A

Omnibus Order on Pending Motions and Dismissing Case

(S.D. Ha., Case No. 0:24-cv-61529-MD, ECF No. 22, Jan. 10,2025)

Filed: January 10,2025

App. 1

Case 0:24-cv-61529-MD Document 22 Entered on FLSD Docket 01/10/2025 Page 1 of 16

UNITED STATES DISTRICT COURT

SOUTHERN DISTRICT OF FLORIDA

CASE NO. 24-61529-CIV-DAMIAN

EMMET O’BRIEN,

Plaintiff,

v.

PAUL FLICK and SAMUEL

CHAMBERLAIN,

Defendants.

OMNIBUS ORDER ON PENDING MOTIONS

AND DISMISSING CASE

THIS CAUSE is before the Court on Defendant Paul Flick’s Motion to Dismiss First

Amended Complaint and Motion to Strike, filed September 26, 2024 [ECF No. 9 (“Flick’s

MTD”)]; Defendant Samuel Chamberlain’s Rule 12(b)(6) Motion to Dismiss, filed November

4, 2024 [ECF Nos. 11 and 12 (“Chamberlain’s MTD”)]; Plaintiff, Emmet O’Brien’s, Motion

for Leave to File Sur-Reply to Defendant Paul Flick’s Reply in Support of Motion to Dismiss

First Amended Complaint, filed October 17, 2024 [ECF No. 16 (the “Motion for Leave”)];

and Defendant Paul Flick’s Motion to Strike and for Sanctions [ECF No. 18 (the “Motion to

Strike”)] (collectively, the “Motions”).

THE COURT has considered the Motions and the parties’ memoranda [ECF Nos. 13,

15, 17, 19, 20, and 21], the applicable law, and the pertinent portions of the record and is

otherwise fully advised in the premises.

For the reasons detailed below, this Court concludes the Complaint is due to be

dismissed with prejudice.

1

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I.

BACKGROUND

A. Relevant Facts

Plaintiff, Emmet O’Brien, was the CEO and majority shareholder of the entity NOH20 USA, Inc. Defendants, Paul Flick and Samuel Chamberlain, invested in N0-H20 USA,

Inc. After their business relationship fell apart, Defendants, in their capacities as managing

members of two different limited liability companies (“LLCs”),asserted claims against

O’Brien in two separate cases in this District,.

In March 2023, Defendant Flick, as Managing Member of AE Capital Group, LLC

brought claims against O’Brien and NO-H2O USA, Inc. in Case Number 23-cv-60601-RS

(the “AE Capital case”). In the AE Capital case, Flick, through AE Capital Group, LLC,

asserted claims for (1) Violation of Exchange Act Section 10(b) and Rule 10b-5 and (2)

Violation of Florida Code § 517.301, against all Defendants, and (3) Breach of Contract and

(4) Fraud in the Inducement against only N0-H20 USA, Inc., alleging “fraudulent

representations designed to lure investors into purchasing stock in N0-H20 USA.” Id., 5| 2.

According to the Complaint in the AE Capital case, O’Brien and N0-H20 USA “raised

almost $2,000,000.00 for the Stock Sale held in July 2021 based on an inflated $13,000,000.00

pre-money valuation of NO-H2O USA. The money raised is now gone—mostly distributed

to Emmet O’Brien or the Ireland Companies—and the anchor Stock Sale investors have

resigned from the Company’s Board.” Id.

In May 2023, Defendant Chamberlain, as Managing Member of Piccadilly Holdings

II, LLC .asserted claims against O’Brien and No-H2O USA, Inc. in Case Number 23-cv-

60978-DSL. (the “Piccadilly Holdings case”). In the Piccadilly Holdings case, Chamberlain,

through Piccadilly Holdings II, LLC, alleged (1) Violation of Exchange Act Section 10(b) and

2

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Rule 10b-5, (2) Violation of Exchange Act |20, (3) Florida Securities and Investor Protection

Act claims, and (4) Common Law Fraud for “misrepresentations and omissions in connection

with [O’Brien’s] activities in improperly inducing Plaintiffs to purchase securities in NOH2O.” Id. U I. The Complaint in the Piccadilly Holdings case alleges that “O’Brien served as

the CEO of N0-H20 and by virtue of his high-level and controlling position at N0-H20,

directly participated in the management of the Company and was privy to information

regarding the ownership of intellectual property, financial statements, and financial condition

. . . [and] is also the majority shareholder of N0-H20” and that “[i]n O’Brien’s overtures to

the Plaintiffs, O’Brien made numerous material representations of fact, and/or omitted

material facts to prevent material misrepresentations, to induce the Plaintiffs into purchasing

the shares of Class A Stock [of N0-H20].” Id. U 6.

B. Procedural History ofthe Instant Case

O’Brien initiated this lawsuit by filing a Complaint on August 20, 2024, over one year

after the above-cited lawsuits were filed against him. [ECF No. 1], On August 23, 2024 this

Court sua sponte dismissed the Complaint on the grounds it was a shotgun pleading and

insufficiently alleged diversity jurisdiction. [ECF No. 5], On September 16, 2024, O’Brien

filed an Amended Complaint [ECF No. 8], which is now the operative pleading.

In the Amended Complaint, O’Brien asserts seven causes of action: (1) Defamation

against Flick (Count I); (2) Defamation against Chamberlain (Count II); (3) Intentional

Infliction of Emotional Distress against Flick (Count III); (4) Intentional Infliction of

Emotional Distress against Chamberlain (Count IV); (5) Tortious Interference with Business

Relationships against Flick (Count V); (6) Tortious Interference with Business Relationships

3

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against Chamberlain (Count VI); and (7) Fraudulent Misrepresentation against Flick (Count

VII).

O’Brien’s claims in the Amended Complaint center, generally, on O’Brien’s

allegations that the Defendants, as a board member and investor, respectively, in No-H2O

Holdings Limited and No-H2O USA, Inc.,1 presented themselves as supporters of O’Brien’s

vision for No-H2O but then, through a series of actions, caused him “lost income, loss of

business value, reputational harm, emotional distress, legal fees, and other damages[.J” Am.

Compl. at 1-2.

On September 26,2024, Flick filed a Motion to Dismiss [ECF No. 9], and on October

4,2024, Chamberlain filed a Motion to Dismiss [ECF Nos. 11 and 12] (together, the “Motions

to Dismiss”). In the Motions to Dismiss, Defendants argue that the Amended Complaint is a

shotgun pleading, that the business-judgment rule applies to bar most (if not all) of O’Brien’s

claims, and that O’Brien has otherwise failed to state a claim in his various causes of action

against them. See generally ECF Nos. 9, 11, and 12.

H.

LEGAL STANDARD

A. Motion to Dismiss

Rule 12(b)(6) provides that a defendant may move to dismiss a complaint that does

not satisfy the applicable pleading requirements for “failure to state a claim upon which relief

can be granted.” Fed. R. Civ. P. 12(b)(6). In considering a Rule 12(b)(6) motion to dismiss,

the court’s review is generally “limited to the four comers of the complaint.” Wilchombe v.

TeeVee Toons, Inc., 555 F.3d 949, 959 (11th Cir. 2009) (quoting St. George v. Pinellas County,

285 F.3d 1334, 1337 (11th Cir. 2002)). The Court must review the complaint in the light most

1 Collectively, “No-H2O.”

4

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favorable to the plaintiff, and it must generally accept the plaintiffs well-pleaded facts as true.

Hishon v. King and Spalding, 467 U.S. 69, 73 (1984). However, pleadings that “are no more

than conclusions[] are not entitled to the assumption of truth. While legal conclusions can

provide the framework of a complaint, they must be supported by factual allegations.”

Ashcroft, 556 U.S. at 679. Dismissal pursuant to a Rule 12(b)(6) motion is warranted “only if

it is clear that no relief could be granted under any set of facts that could be proved consistent

with the allegations of the complaint.” Shands Teaching Hosp, and Clinics, Inc. v. Beech St. Corp.,

208 F.3d 1308,1310 (11th Cir. 2000) (internal quotation marks omitted) (quoting Hishon, 467

U.S. at 73).

Federal Rule of Civil Procedure 8(a)(2) also requires that a pleading contain a “short

and plain statement of the claim” showing the pleader is entitled to relief. Fed. R. Civ. P.

8(a)(2). The complaint must “give the defendant fair notice of what the claim is and the

grounds upon which it rests.” Twombly, 550 U.S. at 555 (cleaned up).

B. Motion to Strike

Federal Rule of Civil Procedure 12(f) provides that a court “may strike from a pleading

an insufficient defense or any redundant, immaterial, impertinent, or scandalous matter.”

Fed. R. Civ. P. 12(f). Although a court has broad discretion when reviewing a motion to

strike, such motions are considered “a drastic remedy” and are often “disfavored by the

courts.” Simmons v. Royal Caribbean Cruises, Ltd., 423 F. Supp. 3d 1350, 1352 (S.D. Fla. 2019)

(Ungaro, J.). Motions to strike are generally denied “unless the matter sought to be omitted

has no possible relationship to the controversy, may confuse the issues, or otherwise prejudice

5

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a party.” Id. (quoting Bank ofAm., N.A. v. GREC Homes IX, LLC, No. 13-21718, 2014 WL

351962, at *4 (S.D. Fla. Jan. 23, 2014) (Altonaga, J.)).

C. Pro Se Litigants

Courts generally construe filings by pro se litigants liberally, but pro se litigants must

comply with the Federal Rules of Civil Procedure and the Local Rules. See Moton v. Cowart,

631 F.3d 1337, 1340 n.2 (11th Cir. 2011) (statingpro se litigants must comply with procedural

rules); see also S.D. Fla. L.R. 1.1 (“When used in these Local Rules, the word ‘counsel’ shall

be construed to apply to a party if that party is proceeding pro se.”).

m.

DISCUSSION

As noted above, Defendants raise several challenges regarding the sufficiency of

O’Brien’s claims. The undersigned has conducted a careful review of the 59-page Amended

Complaint, as well as the parties’ briefs in connection with the pending Motions. Based on

this review, it is the finding of this Court that this case is due to be dismissed because O’Brien

was required to assert the claims now asserted in this lawsuit as compulsory counterclaims

in the previous lawsuits asserted against him in this District. As explained below, this case is

also due to be dismissed as a sanction for O’Brien’s troubling use of citations to non-existent

legal authority and his repeated failure to follow the Local Rules of this Court.

A. O’Brien’s Claims Should Have Been Asserted As Compulsory Counterclaims In Other

Lawsuits.

Pursuant to Federal Rule of Civil Procedure 13(a), if a defending party's counterclaim

arises from the same transaction or occurrence that is the subject matter of the plaintiffs claim,

then the counterclaim is compulsory and must be asserted as a counterclaim to the original

suit. See Fed. R. Civ. P. 13(a). Under Rule 13(a), a party “must state” any compulsory

counterclaim it has “at the time” it serves its answer, if it knew the grounds for the

6

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counterclaim at that time. Id. “To effect the purpose of Rule 13, the consequence for failing

to assert a compulsory counterclaim is a bar against the assertion of that claim in any other

action.” Univalor Tr., SA v. Columbia Petroleum, LLC, 315 F.R.D. 374, 380 (S.D. Ala. 2016). In

other words, “[c]ompulsory counterclaims which are not brought are ‘thereafter barred.’”

Nippon Credit Bank, Ltd. v. Matthews, 291 F.3d 738, 755 (11th Cir. 2002), abrogated on other

grounds by Diamond Crystal Brands, Inc. v. Food Movers Int’l, Inc., 593 F.3d 1249 (11th Cir. 2010).

To determine whether a counterclaim is compulsory, the Eleventh Circuit applies the

“logical relationship” test. Republic Health Corp. v. Lifemark Hosps, ofFla., Inc., 755 F.2d 1453,

1455 (11th Cir. 1985). This inquiry involves considering whether “the same operative facts

serve as the basis of both claims or the aggregate core of facts upon which the claim rests

activate additional legal rights, otherwise dormant, in the defendant.” Id. “The purpose of the

compulsory counterclaim rule is to eliminate multiplicity of litigation.” Montgomery Ward Dev.

Corp. v. Juster, 932 F.2d 1378, 1381 (11th Cir. 1991) (discussing state court equivalent). This

is a loose standard, which permits a “broad realistic interpretation in the interest of avoiding

a multiplicity of suits.” See U.S. v. Amtreco, Inc., 790 F.Supp. 1576, 1580 (M.D. Ga. 1992)

(quoting Plant v. Blazer Fin. Serv., 598 F.2d 1357,1361 (5th Cir. 1979)). The objectives of Rule

13(a) are to provide complete relief to the parties in a single suit, to promote judicial economy,

and to avoid the inefficiencies of piecemeal litigation. John Alden Life Ins. Co. v. Cavendes, 591

F.Supp. 362, 366 (S.D. Fla. 1984) (Aronovitz, J.).

Both Defendants here aver that O’Brien asserted the claims in the instant action as

retaliation for their prior lawsuits against O’Brien. See Flick’s MTD at 2 (“In retaliation [to

the filing of other lawsuits filed against O’Brien], Mr. O’Brien filed this lawsuit.”);

Chamberlain’s MTD at 1-2 (describing the instant suit as a “retaliation for the actions

7

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previously filed against O’Brien and No-H2O USA, Inc.... seek[ing] to blame [Defendants]

for the failings of No-H2O . . . [and] airing of grievances. . . attempting] to point the blame

for the failure of No-H2O away from O’Brien.”).

The undersigned has reviewed the claims in the two previous lawsuits filed by the

Defendants against O’Brien and compared them with the claims O’Brien asserts in this

lawsuit.2 Based upon this review, this Court concludes that O’Brien’s claims in this case fall

within the scope of Rule 13(a) as compulsory counterclaims that he was required to assert in

the two previous suits filed against him. O’Brien’s claims in this case share a logical

relationship with each of the prior suits: they arise out of the same transaction or occurrence,

namely the unraveling of the business relationships surrounding No-H2O since the

involvement of Flick and Chamberlain in that business began in 2020. Stated simply,

“separate trials . .. would involve a substantial duplication of effort and time . . . .” Goings v.

Advanced Sys., Inc. of Suncoast, 2008 WL 4195889, *2 (M.D. Fla. Sept. 12, 2008). O’Brien

asserted his Answer to Flick’s suit on July 10,2023 (see Case No. 23-cv-60601-RS at ECF No.

15), and his Answer to Chamberlain’s suit on August 29, 2023 (see 23-cv-60978-DSL at ECF

No. 25). O’Brien did not timely assert any counterclaims against either Flick or Chamberlain

in either suit, despite each lawsuit being about the business relationship between each

Defendant and O’Brien vis-a-vis No-H2O—the subject matter of the instant lawsuit.3

2 The Court may consider these dockets—and the filings contained therein—because courts

may take judicial notice of public records, such as a pleading filed in another court, since such

documents are “capable of accurate and ready determination by resort to sources whose

accuracy cannot reasonably be questioned. ” Bryantv. AvadoBrands, Inc., 187F.3d 1271, 1278

(11th Cir. 1999) (quoting Fed. R. Evid. 201(b)(2)).

3 This Court is aware that O’Brien belatedly moved for leave to amend his Answers to assert

counterclaims in both cases, and that each attempt was denied by the district court for

multiple, redundant reasons. See Case No. 23-cv-60601-RS at ECF No. 77, and Case No. 23-

8

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Rule 13(a) applies to counterclaims that have “matured at the time” the defendant

serves his pleadings. 6 Wright and Miller, Federal Practice and Procedure § 1411, at 55. This

Court has examined the Amended Complaint with this requirement in mind. While O’Brien

includes factual allegations in the Amended Complaint involving events that occurred after

July and August 2023, (e.g. Am. Compl.

59 (alleging a September 15, 2023 email)), each

Count involves a series of allegations detailing behavior alleged to have commenced well

before summer 2023—and, more importantly—known to O’Brien well before that time. Thus,

even if the Amended Complaint contains additional allegations from after summer 2023, the

basis for each of O’Brien’s counterclaims was known to him at the time he asserted the

Answers in the earlier suits filed against him. Put differently, O’Brien’s allegations do not

involve counterclaims which were merely “likely to arise” or were “contingent” at the time

O’Brien served each Answer in the previous lawsuits. See Slavics v. Wood, 36 F.R.D. 47 (E.D.

Pa. 1964). Therefore, these counterclaims were “matured” for the purposes of Rule 13(a) at

the time O’Brien filed each Answer. See id.

Because O’Brien’s claims now asserted in the Amended Complaint constitute

compulsory counterclaims that were required to be asserted in the previous lawsuits filed

against him, and he failed to assert them at the time of filing his Answers in those original

suits, O’Brien is barred from asserting the claims in this new action. The Amended Complaint

is therefore due to be dismissed with prejudice, as no amendment can resolve this procedural

bar.

cv-60978-DSL at ECF No. 83. Nevertheless, under Rule 13(a), a party “must state” any

compulsory counterclaim it has “at the time” it serves its answer, if it knew the grounds for

the counterclaim at that time. See Fed. R. Civ. P. 13(a) (emphasis added). Asserting these

claims anew in a separate lawsuit is not an end-run around the compulsory nature of Rule

13(a).

9

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While the Amended Complaint is subject to dismissal for the above-explained reasons,

the undersigned also addresses a separate basis for dismissal due to O’Brien’s troubling

conduct in this litigation.

B. O’Brien’s Use OfFake, Non-Existent Case Citations.

In the Reply in Support of Motion to Dismiss First Amended Complaint and Motion

to Strike [ECF No. 15], Defendant Flick points out that Plaintiff cites two cases in Plaintiffs

Response in Opposition [ECF No. 13] that do not exist. See Reply at 2 n. 1 (“Undersigned was

unable to identify any cases by the name or citation of Snyder v. City of Sanford, 645 So. 2d

1126 (Fla. 5th DCA 1994) or Valley Nat’lBank ofArizona v. A.E. Moses, 617 So. 2d 455 (Fla.

4th DCA 1993 [)] and does not believe any such cases exist.”). The undersigned has conducted

a thorough search for these two cases, and, based on the search, agrees that neither case exists.

In response, O’Brien filed a proposed Sur-Reply, in which he claims that “some case

law references” “may have been cited in error,” but that this was an “honest mistake” and

part of mere “minor clerical errors[,] ” comparable to his having exceeded the applicable page

limits in his briefs without first seeking leave of court.4 O’Brien claims that these errors were

“the result of an inadvertent mix-up while handling multiple case references.” ECF No. 16 at

5-6. This Court is not persuaded by O’Brien’s attempt to explain away fabricated legal

authority.

4 This Court notes that O’Brien indeed exceeded the applicable page limits. While this is a

clear violation of the Local Rules, in light of the liberal pleading standards afforded to pro se

litigants, the Court is willing to tolerate that violation. This Court notes, however, its

disagreement with O’Brien that violation of the page limits rule constitutes only a “minor

clerical error.” See, e.g., Clifford Paper Inc. v. Colonial Press Int'l, Inc., No. 17-22396-CIV, 2017

WL 7311852, at *1 (S.D. Fla. July 19, 2017) (Altonaga, J.) (explaining, while considering a

question of whether litigant exceeded briefing page limits, that “[t]he Court will not permit

an end-run around the Local Rules...”).

10

App. 11

*

Case 0:24-cv-61529-MD Document 22 Entered on FLSD Docket 01/10/2025 Page 11 of 16

There are simply no cases which exist at the citations O’Brien provided, and review of

O’Brien’s briefs reflects that he cites no other case from Florida’s Fifth District Court of

Appeal in 1994, nor from Florida’s Fourth District Court of Appeal in 1993. Thus, his claim

of a “mix-up” with other citations lacks credibility. Nor does any other legitimate case he cites

resemble the fake cases in any way that might conceivably have made such a mix-up possible.

This Court is left with the firm conviction that O’Brien generated his Reply with the assistance

of a generative artificial intelligence program.5 While there is no prohibition against the use

of technology to aid in the preparation of court filings, there is a duty of candor to the Court,

and that duty applies to prose plaintiffs. See Bums v. Windsor Insurance, Co., 31 F.3d 1092, 1095

(HthCir. 1994).

Here, O’Brien has filed a memorandum that is based in part on non-existent case law—

certainly an improper purpose. It is also troubling that O’Brien declines to admit that he used

non-existent case citations, whether they were generated through his use of generative Al or

otherwise, and instead offers what appears to be another misrepresentation to the Court—

that the fake citations were “the result of an inadvertent mix-up while handling multiple case

references.”

The use of non-existent case citations and fake legal authority generated by artificial

intelligence programs has been the topic of many published legal opinions and scholarly

articles as of late. Courts that have addressed the practice consistently agree that the use of

fake legal authority is problematic and warrants sanctions. “Many harms flow from the

submission of fake opinions. The opposing party wastes time and money in exposing the

5 This Court also notes that the Reply is written in a formulaic, sing-song manner—seemingly

lifelike on the surface, yet devoid of much substantive legal argument on the merits—the tell­

tale hallmarks of generative Al work product.

11

App. 12

5

Case 0:24-cv-61529-MD Document 22 Entered on FLSD Docket 01/10/2025 Page 12 of 16

deception. The Court’s time is taken from other important endeavors.... There is potential

harm to the reputation of judges and courts whose names are falsely invoked . . . .” Mata v.

Avianca, Inc., 678 F. Supp. 3d 443, 448-49 (S.D.N.Y. 2023) (also explaining that fictions

citations promote “cynicism about the legal profession and the American judicial system

[because] ... a future litigant may be tempted to defy a judicial ruling by disingenuously

claiming doubt about its authenticity.”). O’Brien’s pro se status does not absolve him of the

responsibility to abide by a duty of candor to the Court. See Kendrick v. Sec’y, Florida Dep’t of

Corr., 21-12686, 2022 WL 2388425, at *3 (11th Cir. July 1, 2022) (“[w]hile it is true prose

pleadings are held to a less strict standard than counseled pleadings and are liberally construed

. . . [pro se litigants] also owe the same duty of candor to the court as imposed on any other

litigant.”).

The imposition of sanctions against parties who submit fake citations is also not

uncommon. See, e.g., Thomas v. Pangbum, CV423-046, 2023 WL 9425765, at *4-5 (S.D. Ga.

Oct. 6,2023) (“Plaintiff did not explain what sources he relied on during his research or where

he found the sham cases.”), report and recommendation adopted, 4:23-CV-46, 2024 WL 329947

(S.D. Ga. Jan. 29, 2024). And pro se litigants are not immune from such sanctions. See Kruse

v. Karlen, 692 S.W.3d 43, 48 (Mo. Ct. App. 2024), reh'g and/or transfer denied (Apr. 9, 2024)

(sanctioning pro se litigant who submitted false citations by imposing a $10,000 fine); see also

Morgan v. Cmty. Against Violence, No. 23 Civ. 353-WPJ/JMR, 2023 WL 6976510, at *7

(D.N.M. Oct. 23, 2023) (explaining that although courts make “some allowances for [a] pro

se Plaintiffs failure to cite to proper legal authority, courts do not make allowances for a

Plaintiff who cites to fake, nonexistent, misleading authorities.” (cleaned up)).

12

App. 13

Case 0:24-cv-61529-MD Document 22 Entered on FLSD Docket 01/10/2025 Page 13 of 16

“The Supreme Court has held that sanctions such as dismissal... are within a court’s

inherent power when a party’s conduct evidences bad faith and an attempt to perpetrate a

fraud on the court.” Qantum Communications Corp. v. Star Broad., Inc., 473 F. Supp. 2d 1249,

1268 (S.D. Fla. 2007) (Martinez, J.) (citing Chambers v. NASCO, Inc., 501 U.S. 32, 40^6

(1991)). In other words, “[i]t is well settled that federal courts have the inherent power to

sanction parties, but the court must make a finding of bad faith on the part of the litigant

before imposing such sanctions.” Harris v. Warden, 498 Fed. Appx. 962, 964, 965 (11th Cir.

2012) (finding “no abuse of discretion in the district court's dismissal” of a pro se plaintiff’s

lawsuit “as a sanction for [that plaintiff’s] abuse of the judicial process.”). Here, the

undersigned has read and considered O’Brien’s proposed Sur-Reply [ECF No. 15], in which

he directly addresses the allegation that he cited non-existent authority. This Court is

ultimately left with the conviction that allowing O’Brien’s bad faith citation of non-existent

authorities would “serve only to foster extensive and needless satellite litigation,” Chambers v.

NASCO, Inc., 501 U.S. 32, 51 (1991), and that O’Brien provides no reason to conclude his

filing was made except in bad faith.6

Based on the above-discussed authorities, considering O’Brien’s history in this District

and the fact that O’Brien continues to neglect his duty of candor to this Court, this Court finds

that the imposition of sanctions against O’Brien is appropriate and warranted. While there is

certainly authority for the imposition of a civil fine against O’Brien, the undersigned

concludes that, in this case, a more appropriate sanction under the circumstances is the

dismissal of this action. See Hood v. Tompkins, 197 Fed. Appx. 818, 819 (11th Cir. 2006) (“A

6 This is not the first time O’Brien has been admonished for making representations to the

Court that lack a good faith basis. See, e.g., Case No. 23-cv-60978, ECF No. 83 at 3-4

(Leibowitz, J.).

13

App. 14

\

Case 0:24-cv-61529-MD Document 22 Entered on FLSD Docket 01/10/2025 Page 14 of 16

district court may impose sanctions if a party knowingly files a pleading [that] contained false

contentions.”) (finding that district court did not abuse its discretion in dismissing case).

Thus, while dismissal is appropriate based upon O’Brien’s failure to assert his

compulsory counterclaims in the lawsuits filed against him, dismissal without prejudice is

also warranted here based on O’Brien’s misrepresentations to the Court.

C. O’Brien’s Failure To Comply With This Court’s Conferral Requirements.

Defendant Flick also avers that O’Brien’s “filings have demonstrated a pattern wherein

Plaintiff has used his prose status as both a sword and a shield.” ECF No. 18 at 3. This Court

agrees.

Specifically, O’Brien filed the Motion for Leave without engaging in the conferral

process required by Local Rule 7.1. Compare ECF No. 16, with S.D. Fla. L.R. 7.1(a)(3). Flick

contends that this is “the latest in a string of motions filed by O’Brien without the required

pre-filing conferral.” ECF No. 18 at 2 (citing the two other cases in this district in which

O’Brien is a litigant). Flick attaches an order in which Judge Smith denied O’Brien’s Motion

for Leave to Amend due in part to O’Brien’s failure to confer. Id. at Ex. A. In response,

O’Brien “acknowledges the importance of adhering to the Local Rules” but argues he has

“faced significant challenges in complying with these procedural requirements due to the

aggressive and unprofessional behavior of opposing counsel.” ECF No 20 at 4. To this end,

he attaches several emails exchanged with Flick’s counsel. See id. at Ex. A.

Again, although he acknowledges the importance of adhering to the Local Rules,

O’Brien fails to acknowledge that he has not complied with them, and he does not suggest

that he will make any effort to comply going forward. To the contrary, O’Brien repeats the

same pattern of disregard for the Local Rules that he has shown in the other cases against him

14

App. 15

t

-Case 0:24-cv-61529-MD Document 22 Entered on FLSD Docket 01/10/2025 Page 15 of 16

in this District.7 At the end of the day, O’Brien demonstrates no remorse for having failed to

abide by the Local Rules’ conferral requirement, and no indication that he plans to abide by

it going forward.

Accordingly, although much of the relief sought in the Motion to Strike is rendered

moot upon the dismissal of the case, this Court finds Defendant Flick has demonstrated that

the Motion to Strike should be granted in part and O’Brien’s Proposed Sur-Reply [ECF No.

16] should be stricken. O’Brien is admonished that any further failures to comply with this

Court’s orders, or the rules of this Court, will result in the imposition of additional sanctions,

including monetary sanctions. Moreover, the Court notes that O’Brien’s repeated refusal to

engage in conferral as required by the Local Rules further supports its finding that this lawsuit

should be dismissed. See Baltimore v. Jim Burke Motors, Auto., 300 Fed. Appx. 703, 707 (11th

Cir. 2008) (finding that, because pro se plaintiff “had engaged in previous litigation and had

been reminded in that case as well as the instant case that she was obligated to comply” with

court orders and general rules, that this plaintiffs “non-compliance was not the result of

mistake or negligence, but was willful misconduct” and thus that dismissal as a sanction was

warranted).

D. Defendants’Other Arguments.

Because this Court concludes O’Brien’s claims are due to be dismissed for the ,

aforementioned reasons, this Court need not consider Defendants’ other arguments in support

of dismissal of the Amended Complaint.

7 The emails O’Brien attaches to his response do not help him here and do not justify O’Brien’s

repeated failure to comply with the Local Rules.

15

App. 16

v

. Case 0:24-cv-61529-MD Document 22 Entered on FLSD Docket 01/10/2025 Page 16 of 16

IV.

CONCLUSION

For the reasons set forth above, this Court finds that the Amended Complaint is due

to be dismissed with prejudice because O’Brien’s claims constitute compulsory counterclaims

he failed but was required to timely assert as a defendant in two other cases. This Court also

finds that O’Brien’s submission of fake authorities, combined with his failure to candidly

acknowledge that mistake along with his pattern of disregarding court orders and the Local

Rules, warrants the imposition of the sanctionof dismissal. Whereas dismissal as a sanction

is generally without prejudice, nevertheless, because there is a basis to dismiss the Amended

Complaint with prejudice, this Court finds that dismissal with prejudice is warranted and

appropriate. Accordingly, it is hereby

ORDERED AND ADJUDGED that this case is DISMISSED WITH PREJUDICE.

The Clerk of Court shall CLOSE this case, and any pending motions are DENIED AS

MOOT. It is further

ORDERED AND ADJUDGED that the Motion to Strike and for Sanctions [ECF

No. 18] is GRANTED IN PART, and ECF No. 16 is STRICKEN.

DONE AND ORDERED in Chambers in the Southern District of Florida this 10th

day of January, 2025.

UNITED STATES DISTRICT JUDGE

cc:

Emmet O’Brien

P.O.Box A01, 04001

Kosice, Slovakia

Prose

16

App. 17

APPENDIX C

Order Denying Petition for Panel Rehearing and Rehearing En Banc

(11th Cir., Case No. 25-10143-D, Nov. 25,2025)

Filed: November 25,2025

App. 24

USCA11 Case: 25-10143

Document: 34-2

Date Filed: 11/25/2025

Page: 1 of 2

tye

Mnifeit JBtafrs (tuirrf nf Appeals

CItrrntf

Jar tye

No. 25-10143

EMMET O'BRIEN,

Plaintiff-Appellant,

versus

PAUL FLICK,

SAMUEL CHAMBERLAIN,

Defendants- Appellees.

Appeal from the United States District Court

for the Southern District of Florida

D.C. Docket No. 0:24-cv-61529-MD

ON PETITION FOR REHEARING AND PETITION FOR

REHEARING EN BANC

Before Newsom, Grant, and Black, Circuit Judges.

PER CURIAM:

The Petition for Rehearing En Banc is DENIED, no judge in

regular active service on the Court having requested that the Court

App. 25

USCA11 Case: 25-10143

2

Document: 34-2

Date Filed: 11/25/2025

Order of the Court

Page: 2 of 2

25-10143

be polled on rehearing en banc. FRAP 40. The Petition for Panel

Rehearing also is DENIED. FRAP 40.

App. 26

Additional material

from this filing is

available in the

Clerk's Office.