His goal? To make the big team, of course. And both times, he went far into the main camp. In the end, he was sent back to London both times without getting into any NHL regular season action.

It paid off – he won two OHL titles, a Memorial Cup, an OHL MVP trophy and two playoff MVP awards. He quickly skyrocketed himself to the top of Toronto’s prospect depth chart, an honor he holds entering his first year of pro hockey.

This year, Cowan knows he’ll be spending the season playing in the city of Toronto. He just isn’t sure which GO Train stop he’s taking to get there yet.

“I’m actually renting off (Fraser Minten),” Cowan said after Day 1 of rookie camp. “He bought a place last year, so I’m gonna rent off him and stay there this year.”

Cowan split his summer between Toronto and London, where he trained with NHLers like Lawson Crouse, Nick Suzuki, and Dylan DeMelo. He’s no stranger to training with pros at this stage in his career. But now that he knows what’s ahead of him over the next few weeks, the pro-level habits are starting to sink in.

Fortunately, that means he’s in good physical shape heading into camp. Cowan said he has added about seven pounds of muscle this summer, standing at 5-foot-11 (and a half, he said) and 190 pounds.

“This is the best I’ve ever felt coming into camp. I feel confident and just excited to get going,” Cowan said.

Cowan’s goal, of course, is to make the Maple Leafs out of camp for the first time. But there’s no shortage of competition, both at center and on the wing, he’ll have to beat out this year. At center, veterans Nicolas Roy and Scott Laughton look penciled in at No. 3 and 4. On the wings, newcomers Matias Maccelli and Dakota Joshua will both be NHL regulars, while Nick Robertson will look to make a good impression after signing a new deal.

So Cowan has his work cut out for him if he’s going to start the season at Scotiabank Arena. But he’s not worried – he’s focused.

“I had the mindset all summer to get better, and my mind’s pretty free right now,” Cowan said. “I’ve got no worries. I know I’ll be playing somewhere in Toronto this year. Obviously, I want to play in the NHL, but I just got to have a good mindset and keep it free.”

Shining in the two-day prospect tournament in Montreal would be a great way to kick off Cowan’s season. The 20-year-old will be Toronto’s most notable player, and while there’s nothing but pride on the line for the winning team, Cowan will want to prove to the Maple Leafs’ management staff that he’s ready for a big role heading into the pre-season.

Cowan takes pride in how his overall game has developed since getting drafted. His offense dropped significantly last regular season, going from 96 in 2023-24 to 69 in 2024-25. But any scout will tell you his impact didn’t diminish, especially in the playoffs where he led all players with 39 points in just 17 games.

“You go back to London and you’re getting coached by the (Dale and Dylan) Hunters,” Cowan said. “You’re gonna learn a lot. So I felt like I just had learn to have better management of the game, when to get pucks in, when to get them out and when to make that risky play.”

Will it improve his odds of making the Leafs out of camp? It certainly won’t hurt. While the next few weeks might be stressful for most players, Cowan is ready to take the opportunity head-on.

“At the end of the day, I’m playing hockey,” Cowan said. “I get paid to play hockey, that’s my goal in life and I’m here and I want to stick here. So you just got to have a free mindset, you know, and just try to enjoy it and live life day by day.”

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