Kevin O’Leary Wins $2.8M Defamation Judgment Against Ben “BitBoy” Armstrong

TLDR

• A Miami federal court entered a $2.8M defamation judgment for Kevin O’Leary.
• Damages included $750K distress, $78K reputational harm, and $2M punitive damages.
• The case focused on March 2025 posts tied to a 2019 fatal boating crash.
• The judge denied Armstrong’s bid to undo default after finding notice and delay.

Shark Tank’s Kevin O’Leary won a $2.8 million defamation judgment in federal court in Miami. The ruling followed a case against Ben Armstrong, a crypto creator known as “BitBoy.” The court entered judgment after Armstrong did not respond or appear during the case. 

The US District Court for the Southern District of Florida set damages after a hearing. The order said Armstrong’s conduct supported punitive damages. The judge also found the posts were made with “actual malice.”

Damages Award and What the Court Ordered

The court awarded O’Leary $750,000 for emotional distress, according to the order. It also awarded $78,000 for harm to his reputation. The judge added $2 million in punitive damages, which brought the total to $2.8 million. The order described O’Leary as a public figure with ongoing media work and business ties. 

O’Leary testified that reputational issues can limit bookings and partnerships. He also described urgent questions from media staff after the posts spread. The court heard expert testimony on online reputation harm and repair costs. The expert used documented post views and a discounted audience estimate. 

The expert then applied a value method to reach $78,000 in reputation damage. The order also addressed O’Leary’s security concerns after the phone number disclosure. O’Leary testified that he increased security spending by about $200,000 per year. He said he changed travel routines and used different entrances at studios.

Posts About Boating Accident and Disclosure of Private Phone Number

The dispute began with posts Armstrong made in March 2025, according to the filings. The posts accused O’Leary of involvement in a fatal boating accident from 2019. O’Leary was a passenger in the incident, and he was not charged. The order noted that O’Leary’s wife faced a charge after the crash. The court record said she was exonerated after a trial. 

The judge cited findings that the other vessel was operating without its lights on. Armstrong’s posts also included O’Leary’s personal phone number, the record said. One post urged followers to “call a real life murderer.” The order said the disclosure led to a brief suspension on the social platform.

O’Leary testified that his phone received hundreds of calls after the number was posted. He said he blocked more than 100 numbers from unknown callers. He also said he could not change the number due to long-standing contacts.

Case Timeline and Failed Effort to Overturn Default

O’Leary filed the defamation action on March 26, 2025, the docket shows. A process server served Armstrong on March 28, 2025, according to the return. Armstrong’s deadline to respond was April 18, 2025, and no response was filed. On April 21, 2025, the court ordered Armstrong to respond by April 25, 2025. The order warned that failure could lead to default. 

Armstrong sent a letter seeking a continuance and said he was jailed in Cobb County, Georgia. The court extended the response deadline to May 2, 2025, and mailed the order. Armstrong still did not file a response, and the clerk entered default on May 6, 2025. The court later granted default on liability and set a damages hearing.

The evidentiary hearing occurred on October 30, 2025, and Armstrong, though notified, did not appear. He later sought to set aside the default, citing incarceration and bipolar disorder. The court denied the request, finding he had notice, delayed nearly a year, and would prejudice O’Leary.

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