The shock of winning $21.4 million in a lottery was nothing compared to the jolts Craig Henshaw felt later.

They were not pleasant.

The story of Craig Henshaw, multi-millionaire, began one day last September when Craig Henshaw, high school teacher, went digging through his pockets for the $35 he had left to pay for some groceries. He had just enough cash to get him through the rest of the week, before the first paycheque of the new school year would come through.

Loud bells and alarms went off. The phone on the lottery machine began to ring.

“Initially, I thought I’d won $21,000,” Henshaw, 43, says. “Then the lady on the other end of the phone chuckled. It turned out that the digital readout on the ticket machine didn’t have enough space for all the digits.”

“No, Mr. Henshaw, you’ve won $21 million!” the lady told him.

The rest of the day, Henshaw says, was “surreal.”

But the thrill of the millions evaporated quickly. Over the next few weeks his world became a whirlwind of broken friendships and financial scams.

Henshaw couldn’t even return to his cozy loft apartment after collecting his cheque. He spent the first few weeks living in a hotel, mainly in an attempt to duck the media and stalkers.

“Six hours after I won, some scam artist had already managed to get my credit card number. The charities started hammering me immediately,” Henshaw says, smacking his fist into his hand.

“My email inbox was full, and my phone was flooded with text messages. People were asking me to pay off student loans. I got 365 texts in the first day.”

Eight months after his windfall, Henshaw is in a reflective mood as we sit in a pub for an interview. Five years ago, I was a student in his classroom at Markville Secondary School in Markham, where he taught woodshop and technology.

Teaching was his passion, and still is. But as odd as it sounds, the money did get in the way.

In the aftermath of his lottery win, what hurt most, he says, was the reaction from his colleagues. Teachers whom Henshaw considered friends were suddenly badgering him to pay off their credit-card bills. His school board email was completely flooded.

The workplace environment became toxic. After a decade of teaching, he made the decision to resign.

“Unfortunately, I’ve had to say goodbye to about 25 per cent of my friends because they were acting really inappropriately,” Henshaw says. “They were asking for money, and being really pushy about it. The friends who I really cherish didn’t really care at all.”

“It was a really sad day for teaching,” says Don Henshaw, Craig’s father. “He was a born teacher. It was all he ever wanted to do, and now he had to leave teaching.”

“The thing about teachers is that you’ll always be a teacher. That’s just who you are,” Craig says. “I could always volunteer. I always taught for the sheer joy of it, and getting a paycheque was just a bonus.”

Consequently, Henshaw now wrestles with his identity. As a teacher, he spent most of his life working hard, more enamored with the passion of being an educator than earning a paycheque. Like many, he worried about his student loans, credit-card debt, and making ends meet until the next payday.

“I used to be the guy who bought no-name cheese, and suddenly I could buy everything in the house just by snapping my fingers. How do you process that? How do you get used to it?” Craig says. “I know a lot of people will say that those are the problems of the 1 per cent. Well, yeah, but I’m still part of the 99 percent. I just have a bunch of money all of a sudden. I didn’t get any sleep at all that first month. I have to figure out who Craig Henshaw is. I’m still working on it.”

Henshaw’s desire to educate is evident in the way he has spent his winnings thus far.

He’s set up education funds for his nieces and nephews. His cleaning lady, whom he described as being on the lower end of the economic spectrum, will be returning to school thanks to his financial aid.

Henshaw believes people should be given a chance to learn. Instead of donating chunks of money to charities, he has opted to set up scholarship funds at his alma mater, the University of Western Ontario.

“I want to call it the Craig Henshaw Nice Guy Award. I want to give it to people who are enrolled in an arts program, that do a lot of graphics work,” Craig says, chuckling. “You know, the ones that always show up early and stay late at the art openings, and they do stuff to make the community a better place. Then there’s going to be the Craig Henshaw Nice Girl Award, which will be the same thing, but for the girls.”

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Even with a near-limitless amount of cash, Henshaw hasn’t embarked on the spending spree many people fantasize about. He now lives in an inconspicuous apartment in downtown Toronto. Nothing about his residence or wardrobe screams the fact that he’s a multi-millionaire. He has assigned himself a steady allowance that’s enough to enjoy life, but modest enough that it wouldn’t turn heads.

Mike Nadal, a career counsellor at York University’s Schulich School of Business, approves of Henshaw’s modest spending strategy.

“There are two rules,” said Nadal, a former financial advisor who spent four years advising high-net-worth clients. “The first is not to lose the money. The second is not to forget rule number one.”

That was easier said than done on that day he picked up his cheque from the Lotto office.

The first thing he did with the money?

“I took everyone out for a celebratory dinner at a steakhouse. I didn’t know my credit card number had been stolen yet, so my card was declined,” Henshaw says. “I had to turn to my father and ask him for his credit card to pay for the meal.”

He’s learned much since then.

“The bank people were really good. They listened for about a month straight. They asked me what I was comfortable with, and told me about the risks with my now-portfolio.”

“You don’t get thrown into the business, you know. It’s not like, ‘Oh, and I want a thousand dollars on this’ or anything. What they do is take your money and invest it. Essentially, I don’t even get my money,” Henshaw says, with a bemused smile. “I get an allowance. It’s not a huge amount, but it’s enough to comfortably enjoy life.”

It has also bought him the time re-establish some family relationships.

“I spent the last 20 years working my ass off to try and be somebody, and I neglected my family,” he says. “Now I get the chance to try and re-establish all of the relationships that I used to wish I had time for.

“I’ve seen my father and mom more in the last six months than I had in years. I was always working. But now I have the time to spend with my family. My parents are in the sunset years of their life, and I want to make that sunset bright-orange.”

Henshaw has heard that it takes about a year for the stress of a lottery win to settle. “I’d like to travel,” he says. “Next winter, I just want to take a month and be a beach bum somewhere.”

At the end of our interview, Craig calls for our bill. I offer to pay, but my former high school teacher will have none of it.

He slices off $70 from a small ball of bills and lays it down on the table.