During his career, Phil Kessel was mostly known for his elite hockey skills and his reputation as a certified funny man. However, he also proved that he has a big heart. In fact, after winning his first Stanley Cup in 2016, Kessel brought the Cup to Toronto—the city that had traded him just one year earlier. Why? Because he had made a promise to a children’s hospital.
Phil Kessel was drafted fifth overall by the Boston Bruins in 2006. Unfortunately, during his rookie season, he missed 11 regular-season games after undergoing surgery for testicular cancer. Then, after three seasons with the Bruins, he was traded to the Toronto Maple Leafs.
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Phil Kessel Iron Man streak
Over the course of his five seasons with the Maple Leafs, Kessel established himself as both an elite point producer and one of the NHL’s most durable players. In fact, he still holds the league’s Iron Man record, appearing in 1,064 consecutive regular-season games—a streak that lasted from 2009 to 2023. Meanwhile, he also built a close relationship with a children’s cancer hospital in Toronto.
Then, ahead of the 2015-16 season, Phil Kessel was traded to the Pittsburgh Penguins. There, he won the first of his three Stanley Cups. As tradition has it, every member of the championship team gets one day with the Stanley Cup.
His day with the Stanley Cup
However, according to the Cup’s longtime keeper, Phil Pritchard, Kessel’s day with hockey’s most famous trophy was unlike anyone else’s.
“They kind of forced him out of Toronto. He wins the Cup in Pittsburgh. We fly to Wisconsin to meet him in his hometown. His sister, mom and dad, his brother are all there. So we do a little party there, it’s about noon. Then he says, ‘We have another stop to make.’ He takes us to the airport, where he had booked a private plane, and he goes, ‘We’re going to Toronto,'” Pritchard said on the Hockey Lifers podcast before continuing.
“So we fly to Toronto. He doesn’t tell the Penguins anything. They don’t know. We land in Toronto, he goes to Canadian Tire and buys 100 blank pucks. Then he goes to Staples, makes color copies of photos, and we head to the cancer hospital in downtown Toronto. He had promised the kids there that if he ever won the Cup, he would spend his day with them. And that’s exactly what he did. It was amazing,” Pritchard recalled.
Ultimately, that story tells you everything you need to know about Phil Kessel.
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