O’Leary Secures $2.8M Victory in Defamation Case vs Bitboy

Kevin O’Leary Prevails in $2.8 Million Defamation Lawsuit Against Ben Armstrong

A federal judge in Miami has issued a default judgment in favor of prominent businessman and television personality Kevin O’Leary against cryptocurrency influencer Ben Armstrong, widely recognized by his online alias “Bitboy.” The ruling came after Armstrong neglected to respond to the legal complaint filed by O’Leary, which centered on allegations of defamation stemming from inflammatory social media statements.

On Friday, Judge Beth Bloom formally ordered Armstrong to compensate O’Leary with nearly $2.83 million in total damages. This substantial award was prompted by a series of provocative posts on the social media platform X, where Armstrong explicitly labeled the Shark Tank investor as a murderer. These accusations were linked to a tragic boating incident in 2019 involving O’Leary and his wife, Linda, during which their vessel collided with another boat, resulting in the unfortunate loss of two lives.

In March 2025, Armstrong amplified his claims across multiple X posts, asserting that O’Leary had disbursed millions of dollars to suppress details of the accident. However, the court documents clarify that Kevin O’Leary was not at the helm of the boat during the collision and was never subjected to any criminal charges related to the event. His wife, Linda O’Leary, faced charges of careless operation of a watercraft but was fully cleared following an extensive 13-day trial. The trial evidence demonstrated that the other boat involved was navigating without its navigation lights activated, contributing significantly to the mishap.

Armstrong’s Actions Escalate with Public Disclosure of O’Leary’s Contact Information

The judge’s detailed order highlighted how Armstrong intensified his campaign of harassment by publicly posting Kevin O’Leary’s personal phone number on X. In a particularly aggressive outburst, he encouraged his substantial follower base to “call a real life murderer.” This provocative action led to Armstrong receiving a 12-hour suspension from the X platform. O’Leary later described how his phone became inundated with calls following the post, causing profound disruptions that reverberated through both his professional endeavors and private life, as noted in the court’s findings.

The default judgment was entered due to Armstrong’s complete failure to engage with the legal proceedings—he neither filed a response to the initial complaint nor made an appearance in court. Breaking down the awarded damages, Judge Bloom mandated $750,000 specifically for emotional distress and mental anguish suffered by O’Leary, an additional $78,000 to address harm to his reputation, and a hefty $2 million in punitive damages designed to deter such reckless behavior in the future.

This courtroom triumph represents yet another significant setback for Ben Armstrong, whose career has been marred by a string of high-profile legal entanglements in recent years. Notably, in 2023, he was ousted from the Bitboy Crypto brand, which had previously amassed a massive audience as one of the leading YouTube channels focused on cryptocurrency news and analysis. His departure from the platform marked a turbulent chapter in his public persona.

Armstrong’s legal troubles have continued unabated. In March, authorities in Florida took him into custody following a series of emails he sent to Georgia Superior Court Judge Kimberly Childs. At the time, Armstrong was representing himself pro se in a legal matter, and the communications were deemed inappropriate. Just a few months later, in July, he faced another arrest in Georgia, this time accused of engaging in harassing phone calls. These incidents underscore a pattern of confrontational behavior that has repeatedly drawn official scrutiny.

Earlier in 2023, Armstrong encountered further legal issues when he was arrested while conducting a livestream outside the residence of a former business associate. During the broadcast, he publicly accused the individual of withholding his Lamborghini vehicle. Such episodes have painted a picture of ongoing volatility in Armstrong’s professional and personal spheres, particularly within the often contentious world of cryptocurrency influencing.

For Kevin O’Leary, known not only for his shrewd business acumen but also for his candid views on investments including cryptocurrencies, this defamation victory serves as a powerful affirmation of the accountability mechanisms available to public figures targeted by unsubstantiated online attacks. The case highlights the growing intersection between social media rhetoric, personal reputation, and judicial oversight in the digital age, especially within niche communities like crypto where influencers wield considerable sway over public opinion.

As the cryptocurrency ecosystem evolves, incidents like this one remind industry participants of the potential consequences of inflammatory statements made in the heat of online discourse. O’Leary’s success in court may set a precedent for others facing similar reputational assaults, emphasizing the importance of factual accuracy and restraint in public communications.