thus turning "a cost centre to Canada" into "a profit centre." Leadership debt and lawsuit In November 2018, O'Leary hired lawyer Joseph Groia and sued Elections Canada and Canada's federal elections commissioner over campaign finance laws which limited candidates to spending only $25,000 of their own money for their leadership campaign. At the time of the lawsuit, O'Leary still owed $430,000 to creditors. O'Leary had proposed to Elections Canada that he pay off the debt now with his own money and fundraise the money later, but was rebuffed, since this would be illegal. O'Leary publicly stated that the law promoted mediocrity since rich people would be discouraged from running and hurt the businesses that had pledged money for his failed leadership campaign. In O'Leary's legal submissions, he argued that the laws preventing the use of personal money over $25,000 were a restriction of his Section 2 Charter right to free expression and the threat of jail time in those laws violated his Section 7 right to security of the person. Personal life O'Leary and his wife, Linda, have been married since 1990. The couple separated in 2011, but they resumed their marriage after two years. Linda now serves as the VP of Marketing for O'Leary Wines. They have two children. Trevor is a graduate of McGill University who works as an engineer at Tesla, while Savannah is a multimedia producer and filmmaker based in New York City. In a 2016 interview, O'Leary stated: "In a successful growing business, it eats your time alive. Then later in life, you can provide for your family things that many others can't have. But because you sacrificed, you're then given the reward of freedom." The O'Learys live in Miami Beach, Florida and Toronto, Ontario. He also maintains a cottage in Muskoka, Ontario, as well as homes in Boston and Geneva, Switzerland. In a 2022 CNBC interview, he mentioned that he has obtained a UAE citizenship in order to be able to partner with Emiratis on investments. O'Leary is a fan of the football team the New England Patriots and claims to watch all of their games, even when he is traveling around the world and games occur during the middle of the night. He is a wine aficionado and belongs to the Confrérie des Chevaliers du Tastevin, an international association of Burgundy wine enthusiasts. He is also a lifelong photographer and has exhibited and