Stuart Skinner signed with the Winnipeg Jets on July 1 with a pretty clear job waiting for him.

Connor Hellebuyck was the starter, and Skinner was there to be the backup, take some of the workload off a goaltender who plays among the most games in the league, and try to get his own career back on track after a difficult season split between the Edmonton Oilers and Pittsburgh Penguins. Winnipeg signed Skinner for two years at $3.75 million per season, giving him some security and a chance to work with longtime Jets goaltending coach Wade Flaherty.

Two months later, Skinner might be Winnipeg's starting goalie.

Hellebuyck publicly requested a trade Thursday after privately asking the Jets to move him several months ago. The 33-year-old said his position hasn't changed and that leaving Winnipeg is the right path for him and his family. Training camp opens in September, leaving general manager Kevin Cheveldayoff with one of the biggest decisions of his tenure.

The decision will have a pretty significant effect on Skinner.

Winnipeg didn't sign him to take Hellebuyck's job. NHL.com still listed Skinner as Hellebuyck's backup at the end of July, and Cheveldayoff said after the signing that Hellebuyck's uncertain future wasn't the reason the Jets pursued Skinner. He was coming off a season in which he went 23-17-9 with an .888 save percentage in 50 games between Edmonton and Pittsburgh.

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Skinner's career has also provided plenty of evidence that a backup or tandem role suits him.

He has played 224 NHL games with a .902 career save percentage, reached consecutive Stanley Cup Finals with Edmonton and finished second in the Calder Trophy voting as a rookie. His workload increased quickly with the Oilers because Edmonton needed him to start, and the results became increasingly uneven. His playoff career included some very good stretches and enough difficult ones that Edmonton questioned its crease during long playoff runs.

Skinner was the hometown goalie playing for a team with Connor McDavid and Leon Draisaitl during years when anything short of a Stanley Cup was treated as a failure. His final season with the Oilers ended with a trade to Pittsburgh, and he finished the 2025-26 season with the lowest save percentage of his NHL career.

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Winnipeg keeps him in a Canadian market with plenty of attention on the local team. Jets fans will be much more present in the day-to-day conversation surrounding the club than Skinner would have experienced in many American markets. He knows what comes with playing goal in Canada and acknowledged the pressure himself after signing with Winnipeg, saying his experience in Edmonton gave him an understanding of the environment he was entering.

Doing it as Hellebuyck's backup was a reasonable situation for Skinner to be in. Doing it as the man replacing Hellebuyck would bring an entirely different amount of attention.

Hellebuyck has owned the Winnipeg crease for a decade. He has won three Vezina Trophies, won the Hart Trophy in 2025 and started 615 games since entering the NHL. His departure would leave Winnipeg without the player who has covered up plenty of problems during his 11 seasons with the organization.

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There may not be another established starter coming through the door.

It all depends on the return for Hellebuyck. Buffalo has already discussed a Hellebuyck trade with Winnipeg, with Sportsnet's Elliotte Friedman reporting during the NHL Draft that the Sabres and Jets had held talks. Hellebuyck was reportedly willing to waive his no-movement clause for Buffalo. Those discussions stalled, and Buffalo remains an obvious team to watch now that Hellebuyck has made his request public.

Ukko-Pekka Luukkonen would change the picture for Skinner.

Luukkonen has been included in versions of a possible Buffalo package for Hellebuyck, and sending him to Winnipeg would give the Jets another NHL goaltender capable of taking a significant share of the starts. The Jets could enter the season with Luukkonen and Skinner sharing the crease while Flaherty works with both. Reports around the earlier Buffalo discussions linked Luukkonen to a potential deal, although no agreement was reached.

A Hellebuyck trade involving forwards, prospects and draft picks leaves a different depth chart.

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Winnipeg's top goaltending prospect, Domenic DiVincentiis, hasn't played an NHL game. He went 13-16-2 with an .896 save percentage in 34 AHL games last season, and there has been little indication that the Jets intend to hand him a substantial role in their organization immediately.

Skinner would be sitting at the top of the depth chart in that situation.

There has already been some thought in Winnipeg that his signing could eventually lead there. The Winnipeg Free Press raised the possibility in July that Skinner could play 50 to 55 games depending on the goalie Winnipeg receives in a Hellebuyck trade, while noting that neither DiVincentiis nor Thomas Milic appeared ready for the backup job.

That would put Skinner back in familiar territory.

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He started 50 games last season. He started 57 for Edmonton in 2022-23 and another 57 the following year. His performance over that schedule has been the issue, not whether he could handle the schedule.

Winnipeg also offers Skinner an opportunity to work with Flaherty, one of the reasons he wanted to sign with the Jets. Skinner said he had heard positive reviews from other NHL goalies about Flaherty and was looking forward to working with him.

He may be getting considerably more work with him than anyone expected.

Hellebuyck wants out; everyone knows that, and the trade market has already included Buffalo. There are also several American teams he would be happy with, fitting with the possibility that the Michigan native and United States Olympic gold medallist would prefer the next stage of his career to come south of the border. His no-movement clause gives him substantial control over where Winnipeg can send him.

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Skinner's place in all of this depends on what Cheveldayoff brings back.

A goalie such as Luukkonen leaves Winnipeg much less worse off. A trade built around skaters, prospects and picks would leave Skinner as the most experienced goalie in the organization by a wide margin.

He came to Winnipeg expecting to back up one of the best goaltenders of his generation.

There is a very real chance he arrives at training camp with Hellebuyck gone and the net sitting there for him.

Thomas Milic

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