KELOWNA — Sam O’Reilly has become one of the more accomplished players in recent Canadian Hockey League history.
But his journey to a third straight Memorial Cup tournament hasn’t been without twists and turns. He has endured detours and a little adversity along the way.
Traded in the NHL. Traded in the OHL.
From ‘once a Knight, always a Knight’ in London to rival Kitchener, he was acquired in January as a trade deadline ringer to put the Rangers over the top — and did so, helping lead them to an Ontario championship sweep of Barrie while earning playoff MVP honours.
“I was really fortunate to grow up as a London Knight and spend my years there and learn from all the great guys and amazing coaches and staff around there. But obviously the trade happened, and I had to turn the page pretty quick,” said O’Reilly.
The forward led the OHL playoffs with 17 goals and won the Red Tilson Trophy as the league’s most outstanding player in the regular season.
If the junior trade was surprising, the NHL swap was even more shocking.
Edmonton had traded up to take O’Reilly with the final pick of the first round, 32nd overall in the 2024 NHL draft, and signed him that October following his first NHL training camp. But last summer, the Oilers set their sights on Hobey Baker winner Ike Howard in hopes of an immediate offensive boost, with the Tampa Bay Lightning targeting O’Reilly in return.
Now his future appears to be in Florida rather than Alberta.
“It has been a lot (of change), but I think that’s what hockey brings and the journey is part of it,” said the 20-year-old centre known for his versatility and maturity. “You just got to be ready for whatever comes at you because nothing is guaranteed in this business. You just have to put your best foot forward and go to work.”
His present focus is here, in Kelowna, where O’Reilly is trying to join Noah Dobson (Acadie-Bathurst Titan in 2018 and Rouyn-Noranda Huskies in 2019) as the only skaters to win consecutive Memorial Cup championships with different teams in the modern tournament era.
“The Memorial Cup is the hardest trophy to win in junior hockey,” O’Reilly said ahead of Monday’s test against WHL champion Everett. “To get here, to get to this tournament three years in a row now, it’s pretty special. So something that we don’t take for granted.”
Defenceman Jared Woolley was also part of that blockbuster after winning two OHL titles with London. O’Reilly drew most of the attention, but Woolley arrived in Kitchener as a quieter addition — another veteran presence leading by example.
Both scored in Friday’s 5-0 win over host Kelowna, with Woolley also dropping the gloves as the Rangers tried to establish themselves physically.
“You’re up 1-0, you don’t typically fight, give them energy, but they were coming hard, so it was more just we’ll show what we’re about. We’re not going to get pushed over here,” said Woolley. “It was a group effort there, not just me dropping the gloves.
“It’s a short tournament. You don’t have much time to leave a mark, so you’ve got to do it early and roll with it.”
When that OHL deal went down, O’Reilly was fresh off winning bronze with Canada at the world juniors in Minnesota, where his role grew throughout the tournament, and he was named one of Canada’s top three players.
Among his teammates there was Kitchener captain Cameron Reid, who was thrilled to join forces instead of facing O’Reilly and Woolley again in the OHL.
“It sucked to play against them, that’s for sure,” said the Rangers’ top defender. “Experience is a lot bigger than people realize, and they’re taking us through it all, and it’s definitely helping us as a team.”
Woolley can certainly speak to O’Reilly’s value, witnessing his impact throughout their OHL careers.
“He’s playing how the game should be played. He scored (against Kelowna), but he’s winning faceoffs, he’s blocking shots, he’s killing penalties,” said Woolley. “And winning is fun. It doesn’t get old.”
Reid and the rest of the Rangers appreciate all of his contributions, too.
“He’s a great player. He competes, and he wants to win really bad, and I think it trickles on to all the other players around us,” Reid said of O’Reilly. “He’s such a reliable guy, and he’s that hockey player that you want on your team for any situation.”
O’Reilly is wired to win, priding himself on doing whatever it takes here and at the next level when he turns pro in the fall.
“Being reliable helps you win games, and it helps you with ice time and all that type of stuff, so whatever my coaches are asking me to do, I’ll try and go do it as best as I can and try to win hockey games.”
This report by The Canadian Press was first published May 25, 2026.
Larry Fisher, The Canadian Press
