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, known as Mr. Wonderful, is a Canadian businessman and television personality. He gained prominence through appearances on Canadian shows like The Lang and O'Leary Exchange and Dragons' Den (2004-2014). O'Leary has been a Shark Tank investor since 2009. He hosted Discovery Channel's Project Earth in 2008. In 2025, he made his feature film debut.

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

1999: Acquisition by Mattel and Subsequent Firing

In 1999, Mattel acquired The Learning Company (TLC) for US$4.2 billion, leading to sales and earnings drops for Mattel and O'Leary's subsequent firing. Shareholders filed a class-action lawsuit accusing Mattel executives, O'Leary, and former TLC CEO Michael Perik of misleading investors.

1999: SoftKey Acquired by Mattel

In 1999, SoftKey, which later changed its name to The Learning Company (TLC), was acquired by Mattel. O'Leary received around six million dollars from the sale but was promptly fired by Mattel. The acquisition led to significant losses for TLC and shareholder lawsuits alleging mismanagement by O'Leary.

2003: Settlement of Shareholder Lawsuit

In 2003, Mattel paid $122 million to settle a class-action lawsuit filed by shareholders who accused Mattel executives, 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 Filed

In May 2005, Reza Satchu and O'Leary's operating partner, Wheeler, filed a $10-million wrongful dismissal lawsuit against O'Leary and Satchu, which was later settled out of court.

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

During a 2011 segment on The Lang & O'Leary Exchange about the Occupy Wall Street protests, Kevin O'Leary criticized Pulitzer Prize-winning 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: Offers Alberta Investment for Notley's Resignation

In January 2016, Kevin O'Leary offered to invest $1 million in the economy of Alberta if Premier Rachel Notley resigned.

February 2016: Criticized by Maxime Bernier

In February 2016, Conservative politician Maxime Bernier criticized Kevin O'Leary for wanting to be prime minister without speaking French; O'Leary responded by promising to learn French.

February 1, 2017: Gun Range Video Controversy

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

November 2018: Sues Elections Canada over Campaign Finance Laws

In November 2018, Kevin O'Leary sued Elections Canada over campaign finance laws, which limited candidates to spending only $25,000 of their own money for their leadership campaign. He argued the law discourages wealthy individuals from running and hurts businesses that had pledged money for his campaign.

August 24, 2019: Involved 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 deaths and subsequent charges against Linda O'Leary and the pilot of the other boat.

August 2021: Ownership Stake in FTX and Spokesperson Role

In August 2021, Kevin O'Leary acquired an ownership stake in the parent companies of FTX.com and FTX.US, becoming a spokesperson and ambassador for FTX.

September 14, 2021: Linda O'Leary Found Not Guilty

On September 14, 2021, Linda O'Leary was found not guilty of careless operation of a vessel in connection to the fatal boat crash that occurred in August 2019.

February 2022: U.S. 11th Circuit Court of Appeals Ruled in Bitconnect Lawsuit

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: Sued in FTX Class-Action Lawsuit

In November 2022, O'Leary, along with other FTX spokespeople, was sued in a class-action lawsuit following FTX's bankruptcy.

2024: Comments on the 2024 U.S. Presidential Election

During the 2024 U.S. presidential election, Kevin O'Leary criticized Kamala Harris for her plan to increase corporate taxes, defended Trump for bank fraud, and expressed happiness and pride in his work after Trump won the election.

2025: Visits Trump Amid Trade Threats

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

May 12, 2026: O'Leary Accused Nonprofits of Chinese Funding

On May 12, 2026, O'Leary accused two Utah-based nonprofit groups opposing the Stratos project, without evidence, of being funded by the Chinese government.