Barstool Lawsuits: Omega Accounting, Defamation, and NLRB

Lawsuits involving Barstool Sports span breach of contract, defamation, labor law, copyright, and gambling regulation, with the company appearing as both plaintiff and defendant. Its most active case as of mid-2026 is an advertising-payment suit Barstool filed in New York federal court; its most publicized recent wins have come in defamation cases where courts treated the disputed statements as opinion rather than fact.

The Active Case: Barstool v. Omega Accounting Solutions

In August 2025, Barstool Sports sued Omega Accounting Solutions and O’Brien Sales & Marketing, an advertising agency that acted as Omega’s intermediary, in the U.S. District Court for the Southern District of New York.¹ The case is before U.S. District Judge Alvin K. Hellerstein.²

Barstool alleges the defendants failed to pay for advertising and sponsorship services delivered between September and December 2022 under a $6 million media buy. The deal made Omega title sponsor of the Barstool Sports Arizona Bowl and included ad placements during Rough N’ Rowdy events, Super Bowl and March Madness programming, spots on Pardon My Take, and a Token CEO podcast appearance by Omega CEO Jay Woods.¹

Barstool invoiced roughly $4.7 million. O’Brien paid about $426,000, leaving an alleged balance of roughly $1.08 million. Omega, according to the complaint, owes between $3.2 million and $4.4 million depending on whether the calculation uses the contract price or the value of services actually delivered.¹ A default judgment was entered against the defendants on May 15, 2026, and a case management plan followed shortly after.²

Defamation Cases

Rapaport v. Barstool Sports

Actor Michael Rapaport sued Barstool Sports, Dave Portnoy, and others in the Southern District of New York in 2018 after Barstool fired him and a public feud broke out. Rapaport alleged defamation, fraud, and wrongful termination of a talent agreement, seeking more than $15 million. He said Barstool personalities had called him a racist, a fraud, a stalker, someone with herpes, and an abuser.³

In March 2021, the district court granted summary judgment for Barstool on the defamation and fraud claims. The judge held the fraud claims were barred under New York law for duplicating the breach of contract claim, and that the alleged defamatory statements were “nonactionable” opinions made in the context of an “online schoolyard brawl.”⁴ The parties settled the remaining breach of contract claims and Barstool’s counterclaim in September 2022, each side bearing its own costs.⁵

On appeal, the Second Circuit affirmed on January 9, 2024, holding that “no reasonable reader or listener could have viewed any of the challenged statements to be conveying any expressed or implied facts.” Labels like “racist” and “fraud,” the court said, lacked a clearly defined meaning and were incapable of being proven true or false in the context of a hyperbolic public feud.⁶

Portnoy v. Insider

In November 2021, Insider published reports in which two women, identified by pseudonyms, described violent and humiliating sexual encounters with Portnoy at his Nantucket home in the summer of 2020, alleging choking and filming without consent. Portnoy called the encounters “100 percent consensual.” Nantucket police said they were not investigating and neither woman pursued criminal charges.⁷

Portnoy sued Insider, CEO Henry Blodget, editor-in-chief Nicholas Carlson, and reporters Julia Black and Melkorka Licea in Massachusetts federal court in February 2022 for defamation and invasion of privacy.⁸ Chief Judge F. Dennis Saylor IV dismissed the case on November 7, 2022. As a public figure, Portnoy had to show “actual malice,” and the court found he could not: Insider had corroborated the accounts with eyewitness statements, medical reports, photographs, and text messages. The court also rejected the invasion of privacy claim, finding that consent and power imbalances in sexual relationships are matters of public concern.⁹ Portnoy appealed, then dropped the appeal in January 2023, with both sides covering their own costs.

The Ole Miss Rumor

In early 2025, Barstool personalities were implicated in spreading a false viral rumor about University of Mississippi student Mary Kate Cornett. Portnoy publicly said “morally we were wrong” and “I wish we didn’t play any part in it.”¹⁰ Cornett said the claims had “practically ruined” her life; her attorney, Monica Uddin, said the incident was grounds for a defamation case, and Cornett indicated she intended to take legal action against Pat McAfee, ESPN, and possibly others.¹¹ As of April 2025, Portnoy said he planned to pursue mediation with Cornett’s legal team, and no formal suit had been filed against Barstool at that time.

NLRB Settlement Over Anti-Union Threats

After employees at The Ringer announced plans to unionize in August 2019, Portnoy posted tweets threatening to fire any Barstool employee who engaged with union organizers. The company also created a fake “Barstool Sports Union” Twitter account to identify pro-union employees. The Freelance Journalists Union, a branch of the Industrial Workers of the World, filed unfair labor practice charges with the National Labor Relations Board.¹²

Barstool settled with the NLRB in December 2019 without admitting to violating the National Labor Relations Act. The company agreed to delete the tweets and the fake account, notify employees of their right to unionize by email and physical postings at its New York headquarters and satellite offices for at least 60 days, and affirm it would not threaten workers who organized.¹²

Copyright Infringement History

Between 2016 and 2018, Barstool faced at least 11 copyright infringement lawsuits, including one from photographer Brigitte Stelzer. All settled.¹³

A 2019 dispute drew wider attention. Comedian Miel Bredouw filed a DMCA takedown after Barstool reposted her video on Twitter without credit. Barstool’s general counsel first offered her a $50 gift card to the company’s online store, then $2,000, to withdraw the claim. When she refused, Barstool filed a formal counter-notice, which under Twitter’s process would have restored the video unless Bredouw sued within 10 to 14 business days. She chose not to litigate, saying it wasn’t “worth the trouble.”¹⁴ Portnoy called the gift card offer “moronic.”¹³

In September 2023, The Daily Beast reported Barstool had operated a network of more than 40 “sock puppet” accounts on X to post copyrighted sports and entertainment videos, which the main Barstool accounts would then repost, effectively shielding the primary accounts from DMCA strikes. Emory law professor Matthew Sag told the outlet that “using sockpuppet accounts to obscure the origin of infringing videos does not make the underlying conduct any less illegal.”¹⁵

Gambling Regulatory Actions and the Penn Divestiture

Barstool’s tie-up with Penn Entertainment for sports betting produced fines and licensing problems across several states.

The Ohio Casino Control Commission fined Penn $250,000 after regulators found that a Barstool College Football Show held near the University of Toledo had promoted sports betting to viewers under 21.¹⁶

The Massachusetts Gaming Commission investigated the same college football show format, and Barstool agreed to bar anyone under 21 from attending its live college shows as a condition of continuing to operate in the state.¹⁷ The Commission also found that Penn Sports Interactive violated state gambling regulations by promoting “Big Cat’s Can’t Lose Parlay,” which it deemed deceptive, and issued a $25,000 fine in a final decision dated August 27, 2024. The Commission noted the company had not acted in “objective bad faith” and had proactively communicated with enforcement officials about the promotion.¹⁸

Portnoy’s public persona created broader licensing friction. Nevada’s Gaming Control Board chairman publicly raised concerns at a December hearing, and Indiana’s Gaming Commission said it was reviewing the matter “as it pertains to Penn’s responsibilities as a licensee.”¹⁹ Massachusetts also flagged Portnoy’s admitted history of problem gambling and Barstool’s appeal to audiences under 21.²⁰ Portnoy said plainly, “we got denied licenses because of me.”²¹

In August 2023, Penn sold 100% of Barstool back to Portnoy for $1, absorbing a pre-tax non-cash loss of between $800 million and $850 million. Penn kept the right to 50% of gross proceeds from any future sale of Barstool.²²

Minihane v. Curtatone Wiretapping Case

Barstool prevailed in a wiretapping suit brought by Joseph Curtatone, then the mayor of Somerville, Massachusetts. Barstool podcast host Kirk Minihane contacted Curtatone after the mayor criticized the Boston Bruins for a promotional partnership with Barstool. Minihane secured the interview by misrepresenting himself as a Boston Globe reporter, though he told Curtatone before the interview began that he was recording, and later published the full audio. Curtatone sued under Massachusetts wiretapping law. On June 14, 2021, the state’s Supreme Judicial Court ruled for Barstool and Minihane, upholding dismissal of the case.²³

1
Sportico. Barstool Omega Accounting Solutions Advertising Lawsuit
2
CourtListener. Barstool Sports, Inc. v. Omega Accounting Solutions, Inc.
3
Greenberg Glusker. Greenberg Glusker Litigation Team Secures Victory in Second Circuit for Client Barstool Sports in Defamation Case
4
Chambers. Greenberg Glusker Prevails on a Motion for Summary Judgment on Behalf of Client Barstool Sports
5
CourtListener. Rapaport v. Barstool Sports Inc. Docket
6
Bloomberg Law. Michael Rapaport Fails to Revive Suit Against Barstool Sports
7
NBC News. Barstool Sports’ Dave Portnoy Denies Sexual Misconduct Allegations
8
Axios. Dave Portnoy Withdraws Appeal of Lawsuit Against Insider
9
Sportico. Dave Portnoy Insider Lawsuit Dismissed
10
NBC News. Dave Portnoy Barstool Sports Ole Miss Rumors
11
NBC News. University of Mississippi Student Speaks About Viral Rumor
12
Bloomberg Law. Barstool Sports Settles With Labor Board Over Anti-Union Tweets
13
Business Insider. Dave Portnoy Barstool Sports Reportedly Sock Puppet Accounts Avoided Copyright
14
The Verge. Barstool Sports Miel Bredouw Twitter DMCA Copyright Strike Video
15
New York Post. Barstool Sports Uses Burner Accounts to Flout Copyright Law
16
Legal Sports Report. Penn Entertainment Barstool Sports Acquisition Closes
17
Legal Sports Report. MA Sports Betting Regulators Probe Penn About Barstool Brand
18
Massachusetts Gaming Commission. Can’t Lose Parlay Final Decision
19
Axios. Barstool Penn Deal Regulators
20
Pechanga.net. Barstool Sports Dave Portnoy Affiliation Slows First Sports Betting License
21
Variety. Barstool Portnoy Gambling Licenses Denied Penn
22
Variety. Dave Portnoy Barstool Sports Paid One Dollar Penn Entertainment
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Greenberg Glusker. Greenberg Glusker Prevails in Massachusetts Supreme Judicial Court on Behalf of Client Barstool Sports