Former prospect cannot help but make some Oilers fans feel buyer's remorse

After a long and hard season, the Canadian Hockey League (CHL) has ended and the Memorial Cup has been awarded to the Kitchener Rangers of the Ontario Hockey League (OHL).

For those who may not be aware, the CHL is comprised of three major junior leagues based in Canada; The Western Hockey League, Quebec Maritimes Junior Hockey League (QMJHL), and the OHL. Following each league's playoffs, the three league champions and one host city from one of the various league cities all compete against each other for the Memorial Cup.

This year, the teams competing were the Kitchener Rangers (OHL), Chicoutimi Sagueneens (QMJHL), Everett Silvertips (WHL), and the host city, Kelowna Rockets (WHL). The clubs were filled with premiere CHL talent comprised of previously drafted players such as; Tij Iginla, Cameron Reid, Lucas Beckman, Carter Bear, and projected 2027 first overall pick Landon DuPont.

Amongst the players were one who stood above the rest, former Edmonton Oilers first round pick, Sam O'Reilly, who was named the Most Valuable Player of the tournament.

Did the Oilers lose the O'Reilly and Howard swap?

Last summer, the Tampa Bay Lightning were unable to come to terms with their own former first round pick, Isaac Howard who was coming off an MVP season of his own, capturing the 2025 Hobey Baker award as the top NCAA men's hockey player. Oilers general manager Stan Bowman took this opportunity to acquire what many felt was a steal, acquiring a prospect at the height of his career up to this point and swapped O'Reilly and Howard one-for-one with the Lightning.

Upon being acquired, Howard promptly signed his entry-level contract to turn pro and join the Oilers, making the team out of camp. In his first NHL season, he struggled mightily producing five points (two goals, three assists) in 29 games while averaging just over 10 minutes of time-on-ice per game.

He did however have a standout season with their American Hockey League affiliate, the Bakersfield Condors scored 50 points (24 goals, 26 assists) for 47 games.

Contrasting this, O'Reilly started the season sidelined with an injury but rejoined the London Knights before being dealt to the Rangers before the OHL trade deadline along with teammate, defenceman Jared Woolley. His scoring took off from his point-per-game 28 in 28 with the Knights to 43 (17 goals, 26 assists) in 28 games after being traded.

The 20 year old maintained his crazy production in the playoffs, scoring 17 goals, adding 11 assists for 28 points in 18 games. At the Memorial Cup tournament, he scored an impressive three goals and five assists in just four games, winning the championship and MVP along the way.

O'Reilly is set to turn pro next season within the Lightning organization, finishing his successful junior career with a trophy cabinet stocked full. He has; three OHL championships, two Memorial Cup championships, an OHL MVP, OHL playoff MVP, and a Memorial Cup MVP along with other awards and honours. He is a proven winner with a projectable style of play who is poised to make Oilers fans questions whether or not they let him slip through their fingers.

That is, unless Howard is able to breakout next season and play a bigger role with the Oilers. Honestly, the true 'winner' of the trade likely will not be known for years as both are prospects currently developing. Both have won MVP awards and both have shown incredible talent outside the NHL, the jury is very much still out.

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