Kevin O’Leary, the businessman and television personality known from Shark Tank, won $2.8 million in a defamation lawsuit against crypto influencer Ben Armstrong, formerly known as BitBoy Crypto, according to Bloomberg. U.S. District Judge Beth Bloom entered a default judgment after Armstrong failed to provide a substantive response.
The ruling includes $78,000 for reputational harm, $750,000 for emotional distress, and $2 million in punitive damages. Armstrong’s posts in late March 2025 accused O’Leary and his wife of murder and alleged they paid millions to cover up a fatal 2019 boating accident in Ontario. The incident killed two people when O’Leary’s boat struck another vessel. O’Leary was a passenger and never charged, while his wife, Linda O’Leary, was charged with careless operation of a vessel but later exonerated after a 13-day trial.
Social media posts and personal impact
Armstrong’s posts drew roughly 156,000 views and included O’Leary’s private cellphone number, urging followers to “call a real life murderer.” Judge Bloom noted,
“In the weeks and months that followed, Armstrong’s posts and the disclosure of O’Leary’s phone number significantly affected him, both in his professional and personal life.”
O’Leary faced a surge of inquiries from business partners about the false claims and had to increase his personal security. The judge added,
“His family believed they had put the traumatic boating accident behind them, but the posts have reopened old wounds.”
Armstrong attempted to vacate the default judgment in January 2026, citing incarceration and mental health conditions, including a bipolar diagnosis. The court rejected the motion, noting Armstrong had been properly served and delayed nearly a year before taking action.
Armstrong’s broader legal troubles
The defamation ruling is part of a string of legal and regulatory setbacks for Armstrong. In March 2025, he was arrested on a fugitive warrant related to threatening emails sent to a Georgia judge, facing two felony counts with potential five- to ten-year sentences. He faced additional charges in June 2025 for six counts of harassing phone calls, according to DLNews.
Armstrong was removed from BitBoy Crypto by its parent company in August 2023 due to a relapse into substance abuse. Weeks later, he was arrested while livestreaming an attempt to confront a former business partner over a disputed Lamborghini.
Previously, Armstrong built BitBoy Crypto into a channel with more than 1 million YouTube subscribers. His tenure included controversy over paid promotions of projects later exposed as scams and a dismissed lawsuit against YouTuber Atozy, aided by a $100,000 donation from crypto trader Jordan “Cobie” Fish.
Regulatory authorities also targeted Armstrong. The CFTC subpoenaed Hit Network, his former employer, in July 2024 as part of a fraud investigation involving 15 tokens. Armstrong and NBA player Jimmy Butler paid $340,000 to settle claims of promoting unregistered securities for Binance.
Kevin O’Leary’s own crypto history
O’Leary previously served as a paid spokesperson for FTX, earning approximately $15.7 million before the exchange’s 2022 collapse. He was later named as a defendant in a class action by FTX investors. He acknowledged the deal was a “bad investment” and lost the entire sum. Despite the collapse, O’Leary publicly expressed willingness to back Sam Bankman-Fried in a new venture. Bankman-Fried was later convicted on seven criminal counts and sentenced to 25 years in prison.
While the $2.8 million judgment is substantial, collecting the award may prove difficult. Reports in late 2025 suggested Armstrong was close to insolvent, with wallets previously linked to him largely drained. The case is filed as O’Leary v. Armstrong, S.D. Fla., No. 1:25-cv-21417.
Gunel Ismayilova
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