Kevin O’Leary just walked away with a $2.8 million courtroom win. The Shark Tank investor secured a default judgment against former crypto influencer Ben Armstrong, better known as BitBoy Crypto.
The funny thing? Armstrong did not even properly defend himself. A federal judge in Florida stepped in and awarded heavy punitive damages after claims surfaced that Armstrong publicly called O’Leary a “murderer.”
- Judge Beth Bloom awarded O’Leary $2 million in punitive damages plus $750,000 for emotional distress.
- The court rejected Armstrong’s attempt to blame the default on mental health struggles and incarceration.
- Armstrong previously taunted O’Leary online, posting his personal phone number and alleging a cover-up regarding a 2019 boat crash.
The Feud Behind Kevin O’Leary Lawsuit
This whole fight traces back to a tragic 2019 boat crash involving O’Leary’s wife, Linda, where two people lost their lives. She was fully acquitted in 2021. Case closed.
Years later, Armstrong went online and ignored that outcome completely. He posted claims saying O’Leary and his wife “murdered a couple and covered it up.” Then it escalated. He shared O’Leary’s private phone number and urged followers to call him, throwing out lines like he was a “rabid dog” going after him.
At one point, Armstrong even mocked critics by asking, “What are you gonna do, sue me?”
Turns out, that is exactly what happened. And on March 26, 2025, he got his answer in court.
Breaking Down the $2.8 Million Judgment
The ruling included $78,000 for reputational damage and $750,000 for emotional distress.
O’Leary even pointed to increased security measures and changes to studio access because of fears tied to Armstrong’s online following.
Then came the real blow. An extra $2 million in punitive damages, meant to send a message. Armstrong had already defaulted after failing to respond to the lawsuit in 2025. He later tried to undo that default in early 2026, arguing incarceration and mental health struggles kept him from defending himself.
The court did not buy it.
This judgment adds to what has already been a brutal stretch for Armstrong, who was pushed out of the HIT Network and is now staring at serious financial fallout.
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