Game 1 of the Stanley Cup Final is on Wednesday, June 4, in Edmonton, and Toronto Maple Leafs fans will see plenty of familiar faces. The Florida Panthers, who are making their third consecutive appearance in the Cup Final, do not have any former Maple Leafs on their roster, but the Edmonton Oilers, who are in their second straight Cup Final, have several.

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Connor Brown, Kasperi Kapanen, John Klingberg, and Calvin Pickard all once donned the Maple Leafs crest and will be looking to win the first Stanley Cup of their careers. Meanwhile, Zach Hyman, who spent several years with the Maple Leafs before joining the Oilers, will be cheering from the press box after suffering a season-ending injury in the Western Conference Final.

Former Maple Leafs Making an Impact

This is a different Oilers team from years past. Instead of being carried by Connor McDavid and Leon Draisaitl, the team’s depth has made a huge impact. Hyman has been his usual productive self with five goals and 11 points through 15 games, but he’s not the only contributor not named McDavid or Draisaitl.

Brown was forced to miss the final two games of the Western Conference Final due to injury but was outstanding before that. Through 14 games, he had five goals and eight points and was a bit part of the penalty kill. He is expected to be ready for Game 1 and should continue to be a valuable member of the Oilers’ roster.

Connor Brown Edmonton OilersConnor Brown, Edmonton Oilers (Amy Irvin / The Hockey Writers)

Kapanen started the playoffs as a healthy scratch, but was called upon for Game 5 of their Second-Round series versus the Vegas Golden Knights. He immediately made an impact, scoring the overtime goal in the deciding game to help his team advance to the Western Conference Final. He’s been a fixture in the lineup ever since, scoring three goals through seven games while throwing 20.33 hits per 60.

Meanwhile, Klingberg has turned back the clock in the postseason. It’s been a remarkable showing for a player many felt was done in the NHL after an ugly 14-game stretch with the Maple Leafs in 2023-24. He’s now healthy and has quickly proven he has plenty left in the tank.

Finally, Pickard got the call partway through the Oilers’ First-Round series versus the LA Kings and rifled off six straight wins. He suffered an injury in that sixth win and was forced to miss several games before returning to a backup role behind the red-hot Stuart Skinner.

Poor Look on Maple Leafs Former Management Regime

All the former Maple Leafs listed above, aside from Klingberg, departed the organization before GM Brad Treliving took over. It was Kyle Dubas, now the GM of the Pittsburgh Penguins, who moved on from all of them. His biggest blunder was allowing Hyman to hit free agency. The Maple Leafs had a lot of money tied in their Core Four of Auston Matthews, Mitch Marner, William Nylander, and John Tavares, but had he spent their cap space more wisely, the team would have had the money to sign Hyman, who has been one of the NHL’s more productive wingers since joining the Oilers.

Kyle Dubas Pittsburgh PenguinsKyle Dubas, Pittsburgh Penguins President of Hockey Ops (Amy Irvin / The Hockey Writers)

Dubas’ other major error was trading Brown to the Ottawa Senators along with Nikita Zaitsev and Michael Carcone for Cody Ceci, Ben Harpur, Aaron Luchuk and a 2020 third-round pick. While Brown isn’t as productive as Hyman, he has shown he can elevate his game in the playoffs and is a strong penalty killer. He’s the type of bottom-six forward who could have helped the Maple Leafs this postseason.

Dubas gets a pass for trading Pickard, as he was nothing more than a journeyman goalie during his time in Toronto and continued to be for several years before joining the Oilers. He’s looked solid as the backup in Edmonton but is not as good as the Maple Leafs’ current duo of Anthony Stolarz and Joseph Woll.

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Treliving’s decision to sign Klingberg as a free agent in 2023 was a head-scratcher. The Swedish defenceman hadn’t been healthy in some time, and it was obvious in his short Maple Leafs tenure that he was playing at less than 100 percent.  

Dubas Not the Only One to Blame

Dubas is rightfully being criticized for letting these players go, but it doesn’t end with him. The recently fired Brendan Shanahan also played a role in these decisions as president of the organization. With Hyman and Brown on the roster, the Maple Leafs would have been a better team and perhaps enjoyed more success in the postseason. Fans are right to point the finger at Toronto’s former management team for moving on from these players who have enjoyed a lot of success since leaving the organization.

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