Igor Shesterkin

The New York Rangers and Vancouver Canucks are two of the NHL’s worst teams this season and are both on the verge of massive roster changes. While both teams face unique challenges, one parallel is that they’ve made a mess of their goaltending finances with pricey extensions that were miscalculations.

The Rangers and Canucks are far from alone in this predicament. High-priced extensions have also burned several other teams at the bottom of the standings, leaving them with goaltenders who had been performing well but whose play fell off a cliff after signing their new deals.

That isn’t necessarily the case for Shesterkin, however, it is the case for Linus Ullmark of the Ottawa Senators, Juuse Saros of the Nashville Predators, and Jacob Markstrom of the New Jersey Devils, who are all making big money on recent contract extensions, with no guarantees their play will turn around. This has left three teams with win-now rosters featuring goaltenders who are vastly overpaid.

It’s become a trend over the past five-plus years that teams signing goaltenders to expensive deals must be seriously concerned about their performance throughout the term of the agreement.

There is concern about every player’s performance after they sign a lucrative long-term deal. However, goaltenders have become a unique cause for concern lately, and it’s hard to say why.

In the late 1990s and throughout the 2000s, many veteran goaltenders on the wrong side of 30 would sign expensive long-term deals without so much as a second thought from their new teams. In July 2002, for example, goalie Curtis Joseph signed a three-year, $24MM contract with the Detroit Red Wings, even though it wasn’t the best offer on the table.

Joseph had a three-year $26MM offer from the Toronto Maple Leafs but opted to move to Detroit. Toronto then pivoted and signed Ed Belfour to a two-year, $13.5MM deal.

By today’s standards, those contracts aren’t eye-popping, and the term is relatively short. But Belfour and Joseph were 37 and 35, respectively, and there was a chance their play would drop off significantly during the brief time they were signed.

Nowadays, it’s hard to imagine a team giving $8MM a season to a 35-year-old goaltender, and Joseph’s deal was inked 23 and a half years ago. The Senators gave Ullmark four years and $8.25MM annually just last year, but he had just turned 32 and was two seasons removed from a Vezina Trophy as the league’s top goaltender.

It was a pricey gamble for Ottawa and hasn’t looked like good value this season, but Ullmark has been dealing with personal issues, so it’s hard to project how the deal will work out long-term.

Circling back to the Rangers and Canucks, they are a tale of two teams whose expensive goaltending has led to team-wide issues, but for wildly different reasons. In Vancouver, Thatcher Demko was signed to a lucrative three-year deal at the start of free agency, worth $8.5MM annually.

It was a gamble by Vancouver, as they hoped the former Vezina Trophy finalist could bounce back from a poor showing last season. Had Demko had a good year, he would have been a candidate to get $9MM or more on a new contract, but Vancouver thought it was wise to jump the queue. It has not turned out well.

If Demko had played well, Vancouver likely would have paid him an AAV slightly higher than the $8.5MM they gave him, but would’ve been on the hook for more term, which would’ve been riskier. Instead, Vancouver made a different bet and is now on the hook for more term than Demko would’ve received in free agency. But hindsight is 20/20, and for the Canucks, they are stuck with the Demko deal, one they’d love to have back.

In New York, it was a different calculation. Rangers’ general manager Chris Drury believed he had a Stanley Cup contender on his hands, which meant doing everything he could to retain his Vezina Trophy-winning goaltender, Igor Shesterkin. Drury moved out his captain, Jacob Trouba, to open up space to sign Shesterkin to a record-breaking eight-year, $92MM contract.

While it was the right on-ice move given Trouba’s cap hit relative to his play, the Rangers have never been the same since the trade. New York fell off a cliff last season and has remained at the bottom of the league this year, despite Shesterkin being good.

But that is the issue: Shesterkin has only been good. In the years leading up to his extension, Shesterkin was elite.

His play in those seasons masked many of the Rangers’ problems and led Drury and New York management to think the team was much better than it actually was. Shesterkin’s goaltending was a mask, hiding the fact that Drury had built a fatally flawed roster that relied too much on out-of-this-world netminding, which was clearly unsustainable.

While the Rangers, Canucks, Devils and Predators aren’t the only teams with pricey goaltending, they are the most apparent examples of paying a premium for goaltending. But even middle-of-the-pack teams can run into issues where their extensions turn into disasters.

There are good examples in Washington: a few years ago, with Darcy Kuemper, who had just won a Stanley Cup, and Philipp Grubauer, who had been solid for years before signing as a free agent with Seattle and becoming unplayable in the NHL. Matt Murray in Ottawa was the same story, but none is more egregious and obvious than Tristan Jarry in Pittsburgh, who was recently dealt.

Pittsburgh is a relevant example because of Stuart Skinner, who has been a revelation with the Penguins but is a UFA at the end of the season. Pittsburgh already has its goalie of the future in tow in Sergey Murashov, and the Penguins would be wise to ride Skinner into the playoffs and then let him walk in the offseason if his salary demands exceed $5MM annually, which they surely will. It should be interesting to see the Skinner story unfold, but there is plenty of evidence that the Penguins would be wise to avoid giving term to a netminder who is unpredictable.