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, also known as Mr. Wonderful, is a Canadian businessman, television personality, and actor. He gained prominence through appearances on Canadian television shows like "The Lang and O'Leary Exchange" and "Dragons' Den" from 2004 to 2014. He is widely known for his role as an investor on the American reality show "Shark Tank" since 2009. O'Leary also hosted Discovery Channel's "Project Earth" in 2008 and made his feature film debut in 2025.

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

1999: TLC Acquired by Mattel; O'Leary Fired

In 1999, The Learning Company (TLC) was acquired by Mattel for US$4.2 billion, and Kevin O'Leary was subsequently fired. The acquisition was later called one of the most disastrous corporate acquisitions in recent business history. Mattel's shareholders later filed a class-action lawsuit.

2003: Mattel settled 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 filed against O'Leary

In May 2005, Reza Satchu and Kevin O'Leary's operating partner, Wheeler, filed a $10-million wrongful dismissal lawsuit, charging that they had altered an agreed-upon compensation deal and illegally reduced Wheeler's share of the profits. The case was settled out of court.

2006: Appeared on Dragons' Den

In 2006, Kevin O'Leary appeared as one of the five follow-up venture capitalists on the Canadian installment of the international Dragons' Den format on CBC. He developed a persona as a blunt, abrasive investor.

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2011: Occupy Wall Street Controversy

During a 2011 segment of The Lang & O'Leary Exchange, Kevin O'Leary criticized Pulitzer Prize-winning journalist Chris Hedges for sounding "like a left-wing nutbar," leading to Hedges' vow to never appear on the show again.

November 2014: O'Leary Funds Penalties

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: Offer to Invest in Alberta's Economy

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

February 2016: Criticism from Maxime Bernier

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

February 1, 2017: Gun Range Video Controversy

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

November 2018: Lawsuit Against Elections Canada

In November 2018, Kevin O'Leary sued Elections Canada over campaign finance laws limiting spending on leadership campaigns.

August 24, 2019: Fatal Boat Crash on Lake Joseph

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.

2019: Expressed Skepticism About Cryptocurrency

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

August 2021: Took Ownership Stake in FTX

In August 2021, it was announced that Kevin O'Leary would take an ownership stake in the parent companies of FTX.com and FTX.US as part of his compensation for becoming a "spokesperson and ambassador" for FTX.

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

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.