Is the president still bitter over a bad business deal?

UNFORGETTABLE SAGAS, SCOOPS AND SCANDALS
 from Toronto Life’slong-form archives

 
 

MARCH 8, 2025

 

Dear reader,

Canada and the United States once enjoyed a steady, committed relationship—the geopolitical equivalent of a happily married couple. But, since Donald Trump’s second ascent to the Oval Office, the relationship has turned bitter. The president’s deluge of tariff and annexation threats have led to countless heated phone calls and angry ultimatums. How did a once relatively blissful dynamic devolve into something so toxic?

One theory is that, like many a counselling-bound pair, one partner is still bitter over decades-old grievances. In 2012, Trump signed on to be the face of a gaudy luxury hotel at Bay and Adelaide. It was meant to be a tribute to excess and a linchpin in the then-burgeoning business district—until dozens of investors claimed that they’d been over-sold on their investments, which were quickly becoming money pits.

In 2016, the business went bust, and a year later, the building’s new owners scrubbed Trump’s name from the marquee. Perhaps, however absurdly, the president feels he has a score to settle with the city he couldn’t conquer. For a look into the multimillion-dollar lawsuit that helped drive Trump out of Toronto, we’re revisiting Leah McLaren’s 2013 feature, “Trumped.”

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Toronto Life features editor Stéphanie Verge

—Maddy Mahoney, features editor

 
 
 
 
 

Trumped

The Trump Tower, downtown’s tallest new condo-hotel, is a monument to excess. And like its tycoon namesake, it’s surrounded by controversy: 38 investors are suing the hotel for millions. Lessons from a post-crash real estate market

BY LEAH MCLAREN | JULY 2, 2013

When developers approached Donald Trump about building a hotel in Toronto, his reality show The Apprentice was riding high in the ratings, and the Trump brand was associated with luxury, success and business prowess. The businessmen worked out a deal to license the Trump name and planned a condo-hotel set-up that would be a model for Manhattan-style luxury living in Toronto. By the time Toronto’s Trump Tower opened in 2012, ten years after the plan was hatched, the financial climate had drastically changed. The hotel now felt like a throwback to a cockier pre-recession era. And deals with its investors, who believed they’d bought into a get-rich-quick scheme, began imploding. Here, Leah McLaren investigates how something so promising went so wrong.

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