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Just visiting? Potential Conservative leader Kevin O’Leary has called Boston “home” for 20+ years

Conservatives might ask Kevin O'Leary where his heart calls "home" after the celebrity millionaire hinted he's considering a run for the leadership of the Conservative Party of Canada.


Where is “home”?

Considering what was said about former Liberal leader Michael Ignatieff, Conservatives might ask Kevin O’Leary where his heart calls “home” after the celebrity millionaire hinted he’s contemplating a run for the leadership of the Conservative Party of Canada.

News that the ex-Dragons’ Den star may covet the Prime Minister’s job comes only days after he offered $1 million dollars for the resignation of Alberta’s democratically elected Premier.

Earlier this week, O’Leary justified that offer and his Paul Revere-like warnings about the economy, explaining he was speaking “as a Canadian taxpayer, as a Canadian citizen, as a proud Canadian”:

In reality, O’Leary moved to Boston, Massachusetts in 1994.

“Boston is home,” the potential Conservative leadership candidate has been heard to say.

“I spend most of my time in Boston,” O’Leary said in 2014, adding that although he has “multiple addresses” around the world, “Boston is my home.”

Contacted by PressProgress, O’Leary’s spokesperson said “Kevin has a home in both Boston and Toronto as well as a cottage in Muskoka.”

When asked if he pays personal income tax in the United States, O’Leary’s spokesperson did not directly specify, but told PressProgress that he “conducts business” in both countries, and “as such, Kevin pays taxes in both Canada and the US.”

O’Leary Funds has invested in emerging markets like Brazil, India, China and Russia, where he is presumably subject to business taxes, as well.

What drew O’Leary to beantown, anyway?

O’Leary says he initially moved to the Boston-area in the mid-1990s when he “bought a company called Spinnaker LLC,” but these days, the would-be saviour of Canada’s oil industry is most happy walking around America’s 10th largest city without a car.

“When the kids went off college, I said to my wife, ‘I’m like everyone else. I want to walk around. Let’s live downtown’,” O’Leary told the Boston Business Journal. “I’m proud to say that I have a parking space. I don’t have a car. I walk everywhere, and I love Boston for that.”

“I like to walk everywhere,” O’Leary told Boston Magazine. “Your life is on foot, which I think is the most beautiful thing about this city. My dentist, doctor, everything is right there. Shopping, wine, food is all within a couple of minutes’ walk.”

“I barely use a car in Boston.”


Some may be surprised to learn O’Leary ranks quality of life and the ability to walk to shops and restaurants ahead of purely financial considerations, like taxes.

The proud Bostonian previously claimed raising taxes on wealthy Canadians will force high-income earners to reconsider “where they live and where they build businesses” and cause a “brain drain” to lower-taxed jurisdictions, but evidence suggests reality is more in line with the reasons he gives for choosing to live in Boston.

A 2013 survey on what entrepreneurs “want in a city” revealed they “rarely cite low tax rates or business-friendly regulations” in deciding where they live and do business.

In fact, the survey showed “specific quality of life factors, such as ‘parks’ and ‘restaurants’ were discussed more frequently than terms related to taxes and regulations.”

Massachusetts has the 5th highest combined federal, state and local taxes in the United States.

Photo illustration: Aloha75, used under Creative Commons license. Facebook.

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