How would a Connor Hellebuyck trade compare to other historic NHL superstar goalie moves?

Smoke is forming around a trade sending Connor Hellebuyck out of Winnipeg. Why?

The Jets missed the playoffs in 2025-26. Hellebuyck had the worst statistical season of his career, posting his first sub-.900 save percentage. His end-of-year comments were eye-popping for Jets fans.

“Complacency is not going to get us moving forward, so something has got to happen."

One season after winning the Presidents' Trophy, the Jets plummeted to seventh in the difficult Central Division. Now 33, Hellebuyck is coming off his first intentional success with an Olympic gold medal win earlier this year. His 1.18 GAA and .956 save percentage in five games led the way for Team USA.

How does this compare to Hasek and Roy?

When Buffalo dealt Hasek to Detroit in 2001, it carried only a one-year option on the Dominator. The trade returned winger Vyacheslav Kozlov — whose best years were already behind him — and a first-round draft pick in 2002. Roy, traded halfway through a four-year deal in 1995, arrived in Colorado with Mike Keane in return for goaltender Jocelyn Thibault and wingers Martin Rucinsky and Andrei Kovalenko. Detroit and Colorado definitively won those goalie trades.

Hellebuyck has five years left on a seven-year, $59.5 million extension he signed in 2023. He has a full No Movement Clause through June 30, 2027. That will reduce to a 10-team approved trade list for the remainder of the contract. Hellebuyck's current cap hit at $8.5 million per year is the third highest goalie cap hit and 54th overall cap hit in the NHL. 

Unlike Hasek, who was nearing the end of his career, Hellebuyck is still in his prime at 33. While older than Roy at the time of his trade, Hellebuyck offers greater contract security than Roy did at the time of the Montreal-Colorado trade. 

Will this actually happen?

Past goalie trades involving the likes of Roy, Hasek and even Robert Luongo came under different circumstances. Hellebuyck is disgruntled, but he's also the most important player in the history of Jets 2.0. With his contract status, Winnipeg can slow-play a trade until they get what they want. The Jets could even choose to keep Hellebuyck until next July when his NMC ends, increasing their leverage in a possible trade. 

Roberto Luongo was famously shocked when he and his 'immovable' 12-year contract were dealt to Florida in 2014. The Jets, for better or worse, do not face the same challenge with Hellebuyck.

The question will linger until someone answers.