oleary-america_thumb-2.png This article is more than 6 years old

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.

Our journalism is powered by readers like you.

We’re an award-winning non-profit news organization that covers topics like social and economic inequality, big business and labour, and right-wing extremism.

Help us build so we can bring to light stories that don’t get the attention they deserve from Canada’s big corporate media outlets.


PressProgress is an award-winning non-profit news organization focused on uncovering and unpacking the news through original investigative and explanatory journalism.

Most Shared

thumb-2022-08-05 News

Doug Ford Quietly Reduced Education Spending By Nearly a Billion Dollars Last Year

Related Stories


Doug Ford’s Government is Offering Education Workers a Big Cut in Wages and Benefits

View the post

Meet Rumneek Johal, PressProgress’ New BC Reporter

View the post

Sex Workers in Western Canada Say Their Health and Safety is Being Undermined by Right-Wing Religious Groups

View the post


Human rights & inclusion

Amira Elghawaby

Here’s The Problem With Hoping Corporations Will Be Socially and Environmentally Responsible On Their Own

View the post
Politics & strategy

Jeremy Appel

The battle of the PACs in Calgary’s municipal election

View the post
Politics & strategy

Jeremy Appel

27 Different Candidates are Vying to be Calgary’s Mayor. Here Are the Biggest Issues at Stake.

View the post
Why do newspapers always have a business section but not a labour section? We’ve launched a free newsletter covering labour issues in Canada.
Get All Your Canadian Labour News in One Place
Why do newspapers always have a business section but not a labour section? Good news! We’ve launched a newsletter covering labour issues in Canada.