Shark Tank’s Kevin O’Leary Awarded $2.8M in Defamation Suit

So Judge Beth Bloom (S.D. Fla.) decided in today’s O’Leary v. Armstrong, The defendant had earlier failed to defend himself, and had default judgment entered against him as to the falsity of his allegations. The findings of fact:

[Kevin] O’Leary is an internationally renowned entrepreneur, investor, and television commentator. He was the founder of The Learning Company, a company that sold software programs for math and reading. He sold The Learning Company to Mattel in the early 2000s and has been investing in hundreds of businesses since then in all 11 sectors of the economy. O’Leary later became widely known for his role on the television show, Shark Tank, where he and the other “Sharks” evaluate and invest in a range of emerging and start-up businesses. Around that same time, he started appearing on American television networks as a frequent contributor on “business affairs, policy, and technology.” In addition to his investing activities and television work, O’Leary also serves as a keynote speaker for major financial institutions. O’Leary’s social media presence spans 11.1 million followers, a substantial portion of whom are entrepreneurs.

O’Leary filed this action against Defendant Ben Armstrong—known publicly as “Bitboy Crypto”—for maliciously publishing defamatory falsehoods calling O’Leary a murderer and claiming O’Leary “paid millions to cover” up his role in a murder….

In 2019, O’Leary and his wife were involved in a boating accident in which their vessel struck another boat, resulting in two fatalities. O’Leary was not operating the boat at the time and was never charged with any violation of law. His wife, Linda O’Leary, was charged with careless operation of a vehicle. After a 13-day trial, she was exonerated after the court found the other vessel had been operating without its lights on.

The accident—and the unsupported allegations that Linda O’Leary had engaged in wrongdoing—had a significant negative impact on O’Leary and his family. In the aftermath, and before Linda’s O’Leary’s exoneration, O’Leary’s speaking engagements “dried up,” leaving him with virtually no income. Production of his primary television program, Shark Tank, was paused for “six months,” effectively putting his entertainment career on hold. Following the trial, O’Leary and his wife spent years working to move past the tragedy. Yet, as detailed below, Armstrong’s March 2025 posts sought to reopen those events by resurrecting false allegations that O’Leary murdered a couple and paid millions to cover it up.

Defendant Armstrong is a formerly prominent crypto influencer who once ranked among the most popular cryptocurrency personalities on X and YouTube, drawing more than a million followers with his promotional content and lavish lifestyle. At the height of his online presence, he amassed over 3.3 million followers across his social media platforms.

Armstrong spent roughly a week in late March 2025 posting on X, accusing O’Leary of murder and asserting that he paid millions to conceal his involvement. Thousands of people viewed and liked those posts. Armstrong escalated his harassment campaign by releasing O’Leary’s private cell phone number and urging his followers to “call a real life murderer.” That tweet—disclosing O’Leary’s cell phone number—resulted in Armstrong being suspended from Twitter for 12 hours. Nevertheless, Armstrong continued to post defamatory content about O’Leary….

Since Armstrong made the posts, O’Leary has been forced to change his approach to security. Armstrong has “a lot of very energetic” followers on social media. Armstrong’s labeling O’Leary as a murderer and encouraging his followers to call O’Leary caused him “100 percent” concerns about his security and personal safety. None of his colleagues at CNN and Fox want to walk out the door with him. Per Fox’s instructions, he no longer enters or exits through the main entrance and instead has a car waiting for him at a side door. O’Leary no longer walks alone in most cities, instead having to hire security: “I mean, you don’t realize how much you like to just walk by yourself until you can’t do it anymore. Like, that’s – which is what this guy has done to me.” He estimates that he now spends an additional $200,000 per year on security and noted that even his staff believes he should have more protection than he currently does. His fears also stem from the fact that many callers have bombarded his personal cell phone in a “rabid” manner, demanding to speak to the murderer….

The court ultimately awarded O’Leary $78K in compensatory damages, $750K in emotional distress damages, and $2M in punitive damages; the opinion has more on each of these items. And the court also declined to set aside the default judgment (something defendant had asked the court on Jan. 9, 2026 to do):

As Defendant concedes, he was served with the Complaint in this matter on March 28, 2025. Defendant sought and was granted a continuance to respond to the Complaint by May 2, 2025. Defendant failed to respond and was properly defaulted on May 6, 2025. Defendant argues his failure to respond “was not due to willful neglect or disregard for judicial proceedings. Rather, his failure to respond was due to two extraordinary circumstances beyond his control: his incarceration and his serious mental health conditions.”

As the Defendant acknowledges, despite his incarceration “he managed to file to a motion for a continuance.” Thus, Defendant asserts his mental health issues prevented his further participation. Specifically, Defendant suffers from bipolar disorder, narcissistic personality disorder, and dissociative identity disorder, which “significantly impaired his ability to understand and respond appropriately to the legal proceedings.” …

Fed. R. Civ. P. 60(b)(1) states that “the court may relieve a party or its legal representative from a final judgment, order, or proceeding for … mistake, inadvertence, surprise, or excusable neglect[.]” To establish mistake, inadvertence, or excusable neglect under Rule 60(b)(1), a defaulting party must show that: “(1) it had a meritorious defense that might have affected the outcome; (2) granting the motion would not result in prejudice to the non-defaulting party; and (3) a good reason existed for failing to reply to the complaint.”

Here, Defendant has failed to establish excusable neglect…. [A] full evidentiary hearing was held on October 30th, 2025, regarding damages. Thus, setting aside the default judgment would cause undue prejudice to Plaintiff. As Plaintiff points out, he spent many hours “preparing motions for default judgment, expert reports, drafting liability decisions, and participating in a full evidentiary hearing on damages where Plaintiff and his expert traveled from out of town to attend.”

Moreover, “[w]hile courts will occasionally rely on the illness or disability of a party or attorney when finding excusable neglect, these cases involve extraordinary circumstances, such as a sudden, unexpected, or catastrophic illness, or the party has pointed to specific facts and circumstances demonstrating why the illness or disability caused them to miss the original deadline.” “Illness alone is not a sufficient basis for setting aside a judgment under Federal Rule 60(b)(1).” While the Defendant cites to various mental health issues as the basis for his failure to respond, he has failed to provide specific facts and circumstances demonstrating why the illness or disability caused him to miss the original deadline. Moreover, Defendant sought a continuance despite the same mental health issues purportedly preventing him from participating further. As such, Defendant’s Motion is denied….

As to Armstrong’s mental condition, he stated that a sealed filing in the case contains “diagnoses of Bipolar disorder, Narcissistic personality disorder, Dissociative identity disorder, and documentation of Cotard’s syndrome (the delusion that he is dead) and Capgras delusion (believing family members are imposters).” He also filed an affidavit from his uncle stating, among other things, “On December 19, 2025, Benjamin informed his psychiatrist, Dr. Diana Woodall, that he believes he is dead and in a waiting room for Hell.” For more on Armstrong and his history with BitBoy Crypto, see this Yahoo Finance (Isaiah Mccall) article. For more on his prosecution for threatening a judge, see this DLNews (Kyle Baird) article.