She swindled more than a hundred victims out of millions of dollars

UNFORGETTABLE SAGAS, SCOOPS AND SCANDALS FROM THE ARCHIVES 

 
 

Dear reader,

Buying a home is a dizzying task. It’s emotionally loaded and, for many, involves the biggest lump-sum investment they’ll ever put down. Then there are the third parties: agents, brokers, consultants, lawyers. The GTA real estate market is a headache to navigate at the best of times, but in the worst-case scenarios, it provides the perfect cover for predators. 

Just this week, dozens of would-be homebuyers accused a man from Brampton of taking deposits for pre-construction homes he had no authority to sell. His alleged con may have as many as 50 victims, some of whom lost their life savings on a development they may never set foot in. 

But few real estate scammers can compare to Courtney Wallis Simpson. She had scale—more than 100 victims—but most of all, she had gall. Throughout the decades she was actively swindling, she relied on charm and her deluded belief that she could do no wrong. This week, we’re revisiting Sarah Treleaven’s 2023 portrait of Simpson, “The Most Charming Fraudster in Real Estate.”

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—Maddy Mahoney
Features editor

 
 
 

THE MOST CHARMING FRAUDSTER IN REAL ESTATE

From a young age, Courtney Wallis Simpson had big plans, and she was ruthlessly ambitious when it came to achieving them. To finance her lifestyle, she hatched a series of property schemes that would cost her victims—more than 100 of them—millions

BY SARAH TRELEAVEN  |  MAY 29, 2023

By the time she was arrested, Courtney Wallis Simpsonhad been defrauding eager real estate investors on and off for two decades. She subsisted on scams and a deluded self-image according to which she was a scrappy underdog, always on the verge of finally getting the wealth and status she deserved. To believe Simpson, she’s alternately a victim of extensive conspiracies; a misunderstood martyr; or an innocent mother, wife and legitimate businesswoman trying her best to have it all. In truth, in the GTA’s red-hot real estate market, she was a predator who saw marks everywhere she looked, even among her friends.

READ THE FULL STORY
 
 

In the July issue: A look at the insatiable political ambitions of Doug Ford. Plus, the thief, his cam girl and the missing $13 million; our Trump-proof guide to shopping local; and the case for digital abstinence. Still not receiving Toronto Life at home? Subscribe today.

 

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