Winning never felt so bad
Toronto Star|April 28, 2024
Collin McLeod received a substantial inheritance, won big on the lottery, then lost it all while he was in jail
NICOLE O'REILLY
Winning never felt so bad

"Before I went to jail, I could have woken up and gone to Bora Bora; when I got out, I had $97," said Collin McLeod. 

After five months behind bars, Collin McLeod emerged from the Hamilton-Wentworth Detention Centre.

A friend was there to greet him.

“You’re not going to be very happy,” said the longtime friend.

“Why?”

“Your money is all gone.”

McLeod would learn he had just $97 left in his account. And it wasn’t only the money that disappeared. Tens of thousands in cryptocurrency had been transferred. His motorhome, storage locker, nearly all his possessions were gone.

Only three years earlier, he won a million dollars in the provincial lottery.

It was, he reflects now, “the worst thing that ever happened to me.”

There was a time in his life when McLeod felt like he couldn’t lose.

He could pick winning slot machines at casinos. He knew he would win on that lottery ticket he bought at a Mac’s variety store on Garth Street at Garrow Drive on Hamilton Mountain.

With his $1 million he also won a free ticket, and that ticket was also a winner: $1,700.

“Pretty wild,” McLeod remembers.

Now, at 62, he’s broke.

After he won the lottery, he was arrested for driving without a licence, and ultimately spent five months in jail on a drug charge before being released on bail.

When he returned to his basement apartment at 330 Mohawk Rd. E., he had been cleaned out. His dad’s ashes. His prized watches, Harley-Davidson gear and high-end kitchenware. He didn’t even have a pair of underwear.

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