Most Talked-About Controversies Linked to Kevin O'Leary

Public opinion and media debates around Kevin O'Leary—discover key moments of controversy.

Kevin O'Leary, a.k.a. "Mr. Wonderful," is a Canadian businessman and TV personality recognized for his appearances on business-related and reality TV shows. He gained prominence through his roles on Canadian programs like SqueezePlay, The Lang and O'Leary Exchange, Dragons' Den, and Redemption Inc. O'Leary expanded his television presence to the U.S. by joining Shark Tank in 2009, further solidifying his image as a shrewd and sometimes ruthless investor.

Sections (4)

Full Timeline Early Life & Education Career & Achievements Controversies & Scandals

1933: The Securities Act of 1933

The U.S. 11th Circuit Court of Appeals ruled in a lawsuit against Bitconnect that the Securities Act of 1933 extends to targeted solicitation using social media in February 2022.

1999: Acquisition by Mattel and Termination

In 1999, The Learning Company was acquired by Mattel for US$4.2 billion, but sales and earnings dropped, leading to Kevin O'Leary's termination and a shareholder lawsuit alleging accounting tricks to hide losses and inflate revenues.

2003: Settlement of Shareholder Lawsuit

In 2003, Mattel paid $122 million to settle a class-action lawsuit filed by shareholders who accused Mattel executives, Kevin O'Leary, and former TLC CEO Michael Perik of misleading investors about the health of TLC and the benefits of its acquisition.

May 2005: Wrongful Dismissal Lawsuit

In May 2005, Reza Satchu and O'Leary's operating partner, Wheeler, filed a $10-million wrongful dismissal lawsuit, alleging altered compensation and reduced profit share. The case was settled out of court.

2011: Criticizing Chris Hedges on The Lang & O'Leary Exchange

During a 2011 segment of "The Lang & O'Leary Exchange" about the Occupy Wall Street protests, Kevin O'Leary criticized journalist Chris Hedges, leading to controversy and a violation of CBC's journalistic standards.

November 2014: Penalties for Securities Act Violations

In November 2014, O'Leary Funds Management agreed to pay penalties to the Autorité des marchés financiers for violating certain technical provisions of the Securities Act.

January 2016: Offering investment in Alberta for Premier's resignation

In January 2016, Kevin O'Leary offered to invest $1 million in Alberta's economy in exchange for the resignation of Premier Rachel Notley.

February 2016: Criticized by Maxime Bernier

In February 2016, Conservative Quebecois politician Maxime Bernier criticized Kevin O'Leary, calling him a "tourist" for wanting to be prime minister without speaking French.

February 1, 2017: Posting controversial gun range video

On February 1, 2017, Kevin O'Leary posted a video of himself shooting at a Miami gun range, which was later removed from Facebook due to its insensitivity to the Quebec City mosque shooting funeral. He apologized for the timing of the post.

November 2018: Suing Elections Canada

In November 2018, Kevin O'Leary sued Elections Canada over campaign finance laws, arguing they limited his ability to spend his own money on his leadership campaign.

August 24, 2019: Involvement in fatal boat crash

On August 24, 2019, Kevin O'Leary and his wife Linda were involved in a fatal boat crash on Lake Joseph in Muskoka, Ontario, resulting in two fatalities.

2019: Skepticism about Cryptocurrency

In 2019, Kevin O'Leary expressed skepticism about cryptocurrency, describing bitcoin as "a digital game" and "useless currency".

February 2022: US Court Ruling on Social Media Solicitations

In February 2022, the U.S. 11th Circuit Court of Appeals ruled in a lawsuit against Bitconnect that the Securities Act of 1933 extends to targeted solicitation using social media.

November 2022: Lawsuit Over FTX

In November 2022, Kevin O'Leary was sued in a class-action lawsuit, alongside other FTX spokespeople, after FTX went bankrupt due to CEO Sam Bankman-Fried's misuse of client funds.

2024: Criticizing Kamala Harris

During the U.S. presidential election of 2024, Kevin O'Leary criticized Democratic presidential candidate Kamala Harris, citing her plan to increase corporate taxes. He also defended Donald Trump for bank fraud.

2025: Visiting Trump at Mar-a-Lago

In 2025, amid President Donald Trump's threats to impose tariffs on Canadian goods and annex Canada, Kevin O'Leary visited Trump at his Mar-a-Lago resort and supported making Canada part of the United States.