Right at the start of the 2023–2024 season—three years ago—Connor Hellebuyck and the Winnipeg Jets agreed to the terms of a seven-year contract extension worth $8.5 million annually.
At the time, the deal caught many by surprise, as few expected the American goaltender to make a long-term commitment to the Canadian city.
Nevertheless, Hellebuyck did sign that long-term contract, and people began to believe he would stay in Winnipeg, Canada, to finish his career.
Well, here we are three years later, with two years of Hellebuyck's famous contract already behind him, and the 33-year-old American goaltender has just requested a trade.
As the third season of his seven-year contract with the Jets approaches, Hellebuyck has asked to be traded elsewhere.
Let's just say that's pretty brazen of him given the mutual commitment he made with the Jets, so it's no surprise this decision is drawing heavy criticism.
In fact, ESPN host Michael Wilbon didn't hold back in his criticism of Hellebuyck.
ESPN's Michael Wilbon absolutely RIPPED into Connor Hellebuyck for requesting a trade early in his long-term contract with the Winnipeg Jets
Wilbon highlighted how the Jets gave Hellebuyck the security and the money he wanted, and the fact that he wants out only two years into… pic.twitter.com/Xhk1EOonjZ
— Gino Hard (@GinoHard_) August 29, 2026
In fact, the American commentator said he would have responded with “go to hell” to Hellebuyck's trade request if he were in charge of the Winnipeg Jets.
That's a pretty strong statement, but we totally understand what Wilbon is trying to make a point by saying that.
He's calling out the fact that it's unacceptable for a player to sign a long-term contract—in this case, a seven-year deal—with a team, only to want to leave that same team after just two years of the contract.
It's bold to ask for such a trade, especially after the Jets offered him the contract of a lifetime.
It's clear that in Winnipeg, analysts, journalists, and fans must be angry and disappointed, and are eagerly awaiting to see what they'll get in return for the American goaltender.
It will be very interesting to see if Hellebuyck heads across the border—and if so, to which team.
I get the feeling that the Minnesota Wild, the Florida Panthers, and the Vegas Golden Knights will be very high on Hellebuyck's wish list, just like Dylan Larkin, who has also requested a trade.
In Brief
– Unbelievable.
RECORD CROWD AT SAPUTO STADIUM for @rosesmtlfc
17,077 people at Saputo Stadium.
A new attendance record for the Super Ligue du Nord; the previous record was 14,518.I've experienced many great moments in this stadium as a player. But this one had a special…
— Patrice Bernier (@pbernier10) August 30, 2026
– Good news.
Tadej Pogacar “is still alive” after his crash at the Vuelta: https://t.co/0VbUZZgqw4 pic.twitter.com/kctCfpSM9V
— TVA Sports (@TVASports) August 30, 2026
– Read this.
— Mikaël Lalancette (@MikLalancette) August 30, 2026
– Magnificent.
What a wonderful speechhttps://t.co/CSsuxzqWqG
— Brad Ziemer (@BradZiemer) August 30, 2026

RECORD CROWD AT SAPUTO STADIUM for