Winnipeg has apparently decided that trading Connor Hellebuyck is a foregone conclusion; the only detail left to sort out is everything else, starting with the return package Buffalo won’t hand over.
That’s the state of the Connor Hellebuyck trade this week. Per Sportsnet’s Nick Kypreos, on the Real Kyper & Bourne show, Buffalo already said no to Zach Benson, in the bluntest terms available to a general manager who isn’t supposed to sound bored yet. “That’s not happening,” Kypreos relayed, which is the sound of a door closing on the one player Winnipeg actually wants.
Benson isn’t a throw-in here. He’s a twenty-year-old left wing who went 13th overall in the 2023 draft and just signed a seven-year, $52.5 million extension with the Buffalo Sabres, exactly the kind of cheap, controllable scorer a team doesn’t trade away for a goaltender, no matter how many trophies that goaltender owns. Buffalo understands this math. Winnipeg, per its own beat reporters, is proceeding as though the math is a rumor.
This is starting to resemble an estate sale held before anyone’s actually moved out. The family is certain the house is going; they’ve told the neighbors, they’ve priced the furniture in their heads, they’ve picked out a smaller place. What they haven’t done is agree with the one interested buyer on what anything costs, and the buyer keeps declining to bid on the item they actually want.
That’s Winnipeg’s 95 percent certainty problem in a sentence. Winnipeg Free Press columnist Mike McIntyre puts the odds of a trade north of 95 percent, and he’s not hedging for the sake of it. He just doesn’t know when the sale closes or who’s signing the check.
McIntyre’s logic tracks well enough. The Winnipeg Jets let Eric Comrie, Hellebuyck’s personal backup and de facto security blanket, walk to San Jose in free agency, then turned around and signed Stuart Skinner to a two-year, $7.5 million deal as this summer’s free agency moves shook out. You don’t make both of those calls if your franchise goaltender is sticking around.
https://x.com/NHLRumourReport/status/2078676203825963514
None of that explains why nobody can close the actual trade. Buffalo and Winnipeg got deep into talks over draft weekend, in the trade frenzy at the draft that swallowed most of it: the Sabres put the No. 4 overall pick and forward Jack Quinn on the table, and Winnipeg wanted that pick outright, without attaching one of its own top-ten selections in return. Buffalo balked, kept the pick, and used it on defenseman Daxon Rudolph instead, according to The Athletic’s David Pagnotta and Murat Ates. That’s the last round of Hellebuyck trade talks falling apart in real time, and it fell apart over the same math problem Winnipeg just ran into with Benson: both sides agree the trade should happen, and neither agrees what it’s worth.
Carolina is the other name attached to this, and it hasn’t moved either. Chris Johnston reports the Carolina Hurricanes were in on everything around July 1 without closing on anything, which leaves Carolina waiting in case Buffalo blinks, content to let two other teams negotiate against each other while doing nothing at all. That’s a fine strategy if you’re Carolina. It’s a lot less fun if you’re Winnipeg, whose leverage shrinks a little more every week the goaltender sits there, still owed five years at $8.5 million, still willing, per Elliotte Friedman, to waive his no-movement clause the moment somebody names a number he likes.
I’ve read Kypreos’s quote about Benson four times now, and it gets flatter each time, which is its own kind of answer. Hellebuyck won three Vezinas, in 2019-20, 2023-24, and 2024-25, and added the 2024-25 Hart Trophy, becoming the first goalie to pull off that double since Carey Price. None of it moves the market the way three years of team control at $52.5 million moves Buffalo’s plans. Winnipeg is 95 percent sure it’s selling off a future Hall of Famer. It just can’t find anyone willing to pay what that’s supposed to cost, including, this week, itself.
