Kevin O’Leary, a television entrepreneur and investor best known for Shark Tank, won a $2.8 million judgment against Ben Armstrong, a crypto content creator who operated under the name BitBoy, in a defamation case tried this week in a Miami federal court.
According to a recent order, the U.S. District Court for the Southern District of Florida awarded O’Leary $750,000 for emotional distress, $78,000 for reputational harm and $2 million in punitive damages after Armstrong failed to appear or respond throughout the proceedings.
The dispute stems from posts Armstrong made in March 2025, accusing O’Leary of being involved in a fatal boating accident in 2019. O’Leary was a passenger in the incident and his wife was later cleared following a trial.
Armstrong’s posts, which attracted approximately 156,000 views, also included O’Leary’s home phone number and encouraged his followers to contact him. The disclosure triggered a suspension on the social platform and prompted O’Leary to increase his annual security spending by about $200,000.
The court concluded that Armstrong acted with actual malice and noted his numerous hostile communications, including messages sent to judges in separate proceedings.
Armstrong moved to vacate the default judgment, citing incarceration and mental health issues, including bipolar disorder.
However, the court denied Armstrong’s request, pointing out that he was indeed aware of the lawsuit and had already been properly served, but waited nearly a year to act.
The court also found that setting aside the default judgment would unfairly prejudice O’Leary, who had already prepared the motions and expert reports and attended a full evidentiary hearing.
