Kevin O’Leary Sues Crypto Influencer Ben "Bitboy" Armstrong for Defamation Over Social Media Claims

Crypto influencer Ben Armstrong, widely recognized as “BitBoy,” is facing a new legal challenge as Shark Tank’s Kevin O’Leary has filed a defamation lawsuit against him. The suit, lodged on March 27, 2025, in Florida’s Southern District Court, stems from a series of social media posts where Armstrong accused O’Leary of murder. This development marks another chapter in Armstrong’s turbulent journey, which has seen his once-thriving crypto presence unravel amid personal and professional controversies.

O’Leary, a Canadian entrepreneur known as “Mr. Wonderful” from his Shark Tank appearances, claims Armstrong spread false and damaging statements about him online. The allegations center on a 2019 boating accident in Ontario that resulted in two fatalities, an incident where O’Leary was a passenger and faced no charges. His wife, Linda, who was driving the boat, was acquitted in 2021 after a trial, yet Armstrong took to social media to label O’Leary “a real-life murderer” and suggested the couple paid to conceal the truth.

The lawsuit filed by O'Leary's lawyers details how Armstrong escalated his attacks by sharing O’Leary’s personal phone number with followers, urging them to contact him, and taunting O’Leary with messages claiming he was untouchable. O’Leary’s legal team asserts these statements were intentional distortions meant to tarnish his reputation and boost Armstrong’s own visibility. They argue Armstrong sought to capitalize on the controversy for personal gain, a pattern they tie to his efforts to reclaim prominence in the crypto community after a series of setbacks.

A Downward Spiral Meets a High-Profile Lawsuit

Armstrong’s troubles began mounting in 2023 when he was removed from HIT Network, the crypto media company he co-founded, following accusations of substance abuse and misconduct. Shortly after, he was arrested while livestreaming outside a former associate’s home, an event where he admitted to having a gun in his vehicle and referenced an affair. That incident ended with a loitering charge, but his legal woes deepened this month with another arrest in Florida, where he was held without bond as a fugitive tied to a separate case in Georgia.

The defamation suit, overseen by Judge Beth Bloom, seeks damages exceeding $75,000 and a jury trial. Court documents highlight Armstrong’s provocative posts, including one where he boasted about being a “rabid dog” clamped onto O’Leary’s leg. O’Leary’s attorneys frame these actions as a calculated bid for attention, pointing to Armstrong’s own words about wanting to “become rich again” through public feuds.

Armstrong’s recent legal entanglements also include a Georgia case where he represented himself and allegedly harassed Judge Kimberly Childs via email, leading to arrest warrants. He acknowledged this, calling Childs “dishonorable” while confirming the emails triggered his fugitive status. This backdrop of chaos only amplifies the stakes of O’Leary’s lawsuit, which paints Armstrong as a figure spiraling out of control.