Craig Henshaw and the Hassles of Winning the Lottery

When we fantasise about winning the lottery, we imagine a world full of glamour and materialism. We know there will be plenty of attention, good and bad, but we’re prepared for it because we’ve seen it happened to so many others… right? Unfortunately, that’s not always the case. For some, winning millions can be a roadblock to the path of happiness, even with a pocket—or suitcase—full of cash. One story that is a perfect example of how things can go bad quickly is that of Lotto Max winner Craig Henshaw.

Lotto Max Winner Craig HenshawSchoolteacher Wins Millions

One day in September 2011, 43-year-old Toronto resident and high school teacher Craig Henshaw was waiting in line at the grocery store searching his pockets for the remaining $35 he had to last him the week. It wasn’t a lot of money, but it was enough, especially since his first paycheque of the school year would soon be on its way. As he was checking out, he purchased a Lotto Max lottery ticket and asked the clerk to scan it.

Suddenly, the store was filled with the sound of alarms, indicating Craig had won. While reading the amount listed on the machine, he was certain he’d won $21,000, but then the phone on the lottery machine rang and he was informed it was much more. In fact, the amount he’d won was so large that there wasn’t nearly enough room for the LCD screen to show it all—he’d just won $21 million.

Naturally, it was a surreal and life-changing experience for him. How couldn’t it be when he’d just become a multi-millionaire in a matter of minutes?

Craig’s Life Turned Upside Down

In a matter of weeks, however, the thrill of winning the lottery started becoming a nightmare for Craig Henshaw. After his win, he wasn’t able to go home, as he knew his apartment complex would be surrounded by the media. Instead, he stayed at a hotel and avoided showing his face in public. In fact, it only took mere hours after his big win that things started to escalate for the worse.

It started with a scammer. On the same day of his win, Henshaw found out that someone had gotten his credit card information and maxed his card out. Beyond that, he’d already started receiving phone calls from foundations requesting donations. It seemed like he couldn’t escape the constant phone calls, text messages, and e-mails. People were even asking him to pay off their student loans as if he were now a big-name celebrity. This situation would be stressful for anyone, but especially for someone who very suddenly had millions to their name. Craig didn’t even have the time to sort his affairs before the hammering began.

Despite his sudden wealth, he’d planned to continue teaching because, just like Powerball winner Les Robins, he considered it his biggest passion and even expected it to be a temporary escape from the reality of being a lottery winner. However, just like Craig couldn’t trust those in his personal life, he couldn’t trust those in his work life either. Immediately, his colleagues began acting out of character. They were constantly asking for money, and most wouldn’t give up. Craig noted that the friends closest to him didn’t care much about his win at all, so soon enough, it became clear what he had to do.

Though teaching had been a major part of his life for the better part of a decade, Craig had to make the upsetting decision to leave his job. His workplace had become toxic. His colleagues were not only asking him for money to pay off their debts, but the school board immediately diverted their attention to his riches. Suddenly, he couldn’t even work without being exposed to people demanding money from him. Winning the lottery was life-changing, but the events that followed were rarely something Craig could reflect on positively. He lost many friends as well as other things he loved. When any sense of normalcy is stripped away, it’s hard to be happy with your situation—even if you do have millions in the bank.

How Did Craig Spend His Winnings?

While Craig knew he was now a wealthy man, he didn’t quite know how to accept it. Like UK Lotto winners Emma Cox and Luke Pittard, who went back to flipping burgers at McDonalds, he was used to working hard and earning his wages; in fact, he preferred it so long as he was teaching. Likewise, it was difficult for him to split away from what his life once was. He was a normal guy who had the same stresses as the rest of us, especially when it came to bills. Winning so much money that he could afford just about anything was a major life change for him, and he admitted he had plenty of trouble processing it. This influenced how he spent his money in a big way.

His first big move was to set up education funds for his nieces and nephews. After, he decided to provide financial aid to the woman who cleans his home, as she was determined to return to school. Both of these actions prove just how devoted to education Craig is, but there’s more.

Western University LogoRather than donating to charity, he decided to take a large chunk of his money to fund scholarships at the University of Western Ontario—his alma mater. During an interview, he indicated he wanted it to be called the “Craig Henshaw Nice Guy Award” and intended for the money to go to students enrolled in an arts program. He also wanted to provide the “Craig Henshaw Nice Girl Award,” which would have the same terms but would be awarded specifically to female students.

Admittedly, Craig chose to be a modest spender. Unlike other lottery winners, he wasn’t adamant about going on luxurious vacations and expensive shopping sprees. Instead, he moved into a low-profile apartment in downtown Toronto and set weekly spending amounts for himself so that he wouldn’t overspend. In fact, he had learned a big lesson on the day of his lottery win. When he took his family out to celebrate at an expensive steakhouse, he hadn’t yet learned that his credit card number had been stolen—so he had to ask his father to pay the bill when his card was declined. This taught him a thing or two about remaining modest and responsible.


We all prefer to think that we’d be able to spend frivolously if we ever won millions in the lottery, but that’s exactly how many winners go broke. Craig Henshaw’s story demonstrates just how important it is to maintain self-control and focus our energy on the people in our lives that matter the most.

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