Dialing for Defamation

Six counts of defamation per se and one count of invasion of privacy: that is the complaint Kevin O’Leary filed against former crypto influencer Ben “BitBoy” Armstrong in Florida federal court. The suit, O’Leary v. Armstrong, No. 1:25-cv-21417 (S.D. Fla.), arises from a series of posts on X accusing O’Leary of murder and publishing his private cell phone number. The complaint is available here (PDF).

Case Overview

On March 26, 2025, Kevin O’Leary, a Canadian entrepreneur residing in Miami-Dade County, Florida, and known as “Mr. Wonderful” from Shark Tank, initiated legal proceedings against Benjamin Armstrong, a Georgia-based former cryptocurrency influencer known as “Bitboy Crypto,” in the United States District Court for the Southern District of Florida (Case No. 1:25-cv-21417). The lawsuit alleges defamation and invasion of privacy, seeking damages exceeding $75,000 and a jury trial.

Parties Involved

• Plaintiff: Kevin O’Leary
  O’Leary is a prominent figure with a successful business background, having built and sold SoftKey for $4.2 billion and starring on Shark Tank. He chairs O’Leary Ventures and is recognized for his entrepreneurial achievements.
• Defendant: Benjamin Armstrong
  Armstrong, once a significant figure in the cryptocurrency space with over 3 million followers across platforms, saw his influence wane in 2023 following his ousting from HIT Network amid allegations of substance abuse and misconduct. His current X following is approximately 100,000, and the complaint suggests his actions are motivated by a desire to regain relevance after personal and professional setbacks, including a divorce and financial losses.

Factual Background

The dispute arises from a 2019 boating accident on Lake Joseph, Canada, where a boat operated by O’Leary’s wife, Linda O’Leary, collided with another vessel, resulting in two deaths. Linda was charged with careless operation but was acquitted after a 13-day trial, with the court finding the other vessel at fault for operating without lights. Kevin O’Leary was not driving and faced no charges.

Alleged Defamatory Actions

Starting on March 17, 2025, Armstrong allegedly launched a campaign of defamation on X, posting over ten messages accusing O’Leary and his wife of murder and claiming they paid millions to cover it up. Specific examples include:

• March 17 X post: “Kevin O’Leary has already verifiably murdered one couple in Toronto” (30.7K views).
• March 19 X post: Disclosed O’Leary’s private cell phone number, urging followers to “call a real life murderer” (18K views, later removed by X).
• March 21 X post: “Daily reminder that @kevinolearytv and his wife Linda O’Leary murdered a couple and paid millions to cover it up” (6.3K views).

These posts, viewed thousands of times including by Florida residents, persisted despite public corrections, such as an AI chatbot stating no evidence supported the claims. The complaint alleges Armstrong acted with actual malice, knowingly or recklessly disregarding the truth, to exploit O’Leary’s fame for attention.

Invasion of Privacy Claim

The complaint also addresses Armstrong’s March 19 X post disclosing O’Leary’s private cell phone number, claiming it violated his privacy, lacked public concern, and led to harassment and distress, further compounding the harm.

Legal Claims: Defamation Per Se and Publication of Private Facts

The complaint includes:

• Counts I-VI: Defamation Per Se – Six counts target specific X posts (March 17, 19, 20, 21), alleging they falsely accuse O’Leary of murder, a crime that harms his reputation and profession, published with actual malice.
• Count VII: Publication of Private Facts – Addresses the phone number disclosure, claiming it was an invasion of privacy causing emotional distress.

What Is Defamation Per Se in Florida?

Under Florida law, a statement is defamation per se when its harmful character is apparent on its face. The recognized categories include statements that accuse a person of a serious crime, that subject the person to hatred, distrust, ridicule, contempt, or disgrace, or that injure the person in a trade or profession. In a case against a non-media defendant, general damages are presumed and the plaintiff need not prove special damages. That presumption is what makes a defamation per se count valuable to a plaintiff.

An accusation of murder is the textbook example of defamation per se, which is why six of the seven counts are pleaded that way. Because O’Leary is a public figure, he must also show actual malice: that Armstrong knew the statements were false or recklessly disregarded whether they were true.

Jurisdiction and Venue

The case is filed under diversity jurisdiction (28 U.S.C. § 1332), as O’Leary (Canadian/Florida) and Armstrong (Georgia) are from different jurisdictions, with damages exceeding $75,000. Personal jurisdiction is based on Florida’s long-arm statute (Fla. Stat. § 48.193), citing Armstrong’s defamatory posts targeting O’Leary, a Florida resident, and his business activities in Florida (e.g., crypto events).

Damages Sought

O’Leary seeks compensatory damages over $75,000, punitive damages, attorneys’ fees, costs, and other relief, emphasizing the significant harm to his reputation, emotional distress, and economic damage caused by Armstrong’s actions.

Read the Complaint

The complaint, including all six defamation per se counts, is attached. Open the O’Leary v. Armstrong complaint (PDF) or use the download button below.

Questions about a defamation per se claim or defense? Contact Cox Law, PLLC or call 813-685-8600.

This post summarizes the allegations of a filed complaint for informational purposes. Allegations are not findings. It is not legal advice and does not create an attorney-client relationship.