Kevin O’Leary, an entrepreneur and television investor best known for Shark Tank, secured a $2.8 million judgment against Ben Armstrong, a crypto content creator who operated under the name BitBoy, in a defamation case decided this week by a federal court in Miami.
According to a recent order, the US District Court for the Southern District of Florida awarded O’Leary $750,000 for emotional distress, $78,000 for harm to his reputation, and $2 million in punitive damages after Armstrong failed to appear or respond throughout the proceeding.
The dispute arose from posts Armstrong made in March 2025, accusing O’Leary of involvement in a fatal boating accident that occurred in 2019. O’Leary was a passenger in the incident, and his wife was later cleared of wrongdoing following a trial.
Armstrong’s posts, which drew roughly 156,000 views, also included O’Leary’s personal phone number and encouraged followers to contact him. The disclosure triggered a suspension on the social platform and prompted O’Leary to increase his annual security spending by an estimated $200,000.
The court found that Armstrong acted with actual malice and noted his pattern of hostile communications, including messages sent to judges in separate proceedings.
Armstrong sought to have the default judgment overturned, citing incarceration and mental health conditions, including bipolar disorder.
However, the court rejected Armstrong’s request, noting that he had actual notice of the lawsuit and had already been properly served, yet he 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 had attended a full evidentiary hearing.
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