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 television shows like The Lang and O'Leary Exchange and Dragons' Den (2004-2014). He also hosted Discovery Channel's Project Earth in 2008. Since 2009, O'Leary has been a prominent investor on Shark Tank, the American version of Dragons' Den, and appeared as Milton Rockwell in Marty Supreme(2025).

Sections (4)

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

1933: Securities Act of 1933

In November 2022, Kevin O'Leary along with other FTX spokespeople, were sued and the lawsuit cited that 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.

1999: Mattel Acquires The Learning Company and Fires O'Leary

In 1999, Mattel acquired The Learning Company for US$4.2 billion, and O'Leary was subsequently fired. Mattel experienced a loss of US$105 million, leading to a drop in stock value and a shareholder lawsuit accusing O'Leary of misleading investors.

2003: Mattel Settles 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 Against O'Leary and Satchu

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

2011: Occupy Wall Street Criticism

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 controversy and a CBC ombudsman finding O'Leary's behavior to be a violation of journalistic standards.

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November 2014: O'Leary Funds Penalized for Securities Act Violations

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

January 2016: Offer to Invest in Alberta

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: Bernier's Criticism

In February 2016, Maxime Bernier criticized Kevin O'Leary, calling him a "tourist" for wanting to be prime minister without being able to speak French. O'Leary stated that he was taking French lessons.

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 removed from Facebook out of respect for the Quebec City mosque shooting. He later apologized.

November 2018: Sues Elections Canada

In November 2018, Kevin O'Leary sued Elections Canada and Canada's federal elections commissioner over campaign finance laws that limited candidates to spending only $25,000 of their own money. At the time of the lawsuit, O'Leary still owed $430,000 to creditors.

August 24, 2019: 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. O'Leary cooperated with the police investigation.

2019: O'Leary Expresses Skepticism About Cryptocurrency

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

August 2021: O'Leary Becomes Spokesperson for FTX

In August 2021, O'Leary announced he would take an ownership stake in the parent companies of FTX as compensation for 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 August 2019 boat crash.

February 2022: U.S. 11th Circuit Court of Appeals Rules on Securities Act

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: O'Leary Sued in Class-Action Lawsuit

In November 2022, O'Leary, along with other spokespeople for FTX, was sued in a class-action lawsuit following FTX's bankruptcy due to CEO Sam Bankman-Fried's misuse of client funds. O'Leary lost $9.7 million in digital assets.

2024: Criticism of Kamala Harris's plan to increase corporate taxes.

During the U.S. presidential election of 2024, O'Leary criticized Democratic presidential candidate Kamala Harris, citing her plan to increase corporate taxes. He also defended Trump for bank fraud. After Donald Trump won the election, O'Leary said he was very happy with the outcome and that he was "very proud of the work I did" during the campaign.

2025: Visit to Mar-a-Lago

Amid President Donald Trump's threats in 2025 to impose 25% 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.