Going into this season, the Winnipeg Jets were picked by many to win the Stanley Cup. Coming off of a Conference Final appearance last season, it made sense that the team would take the next step by getting to the Stanley Cup Final and winning it. That did not happen, as the Jets fell in a close, hard-fought six-game series against the St Louis Blues, and now Winnipeg faces many decisions they have to make on expiring contract players this summer.

Trade deadline pickup Kevin Hayes (currently making $5.175 million), depth forwards Brandon Tanev ($1.15 million) and Par Lindholm ($925,000), as well as defensemen Tyler Myers ($5.5 million) and Ben Chiarot ($1.4 million) are all unrestricted free agents. Forwards Andrew Copp ($1 million), Kyle Connor ($925,000), and Patrik Laine ($925,000), defensemen Jacob Trouba ($5.5 million), Nathan Beaulieu ($2.4 million), and Joe Morrow ($1 million), and goaltenders Laurent Brossoit ($650,000) and Eric Comrie ($650,000) are all restricted free agents. Restricted free agency means the Jets have rights to those players first, or they can let them walk into unrestricted free agency for the rest of the league to pounce.

The Jets currently have a projected 28 million in cap space assuming the cap limit goes to $83 million next season. Connor and Laine are due for big raises (probably between $6.5 and $9 million), as Connor is a 30 goal scorer and consistent performer, while Laine is an incredible 40+ goal scorer, but is inconsistent and had a down year. Hayes, Copp, Tanev, and Chiarot are all due for moderate raises. Trouba has had contentious relations with management in the past and is seeking bigger money after a 50 point season on the blue line, while Myers is older and inconsistent.

Realistically, the Jets will have to let a couple of these free agents go and/or make trades of other players with overvalued contracts, such as Bryan Little ($5.3 million until 2024), Mathieu Perreault ($4.1 million until 2021), and Dmitry Kulikov ($4.33 million until 2020). Trouba's recent comments in season exit interviews make it seem like he isn't willing to take less money. making it plausible for the Jets to trade his rights to another team. Nikolaj Ehlers makes $6 million per year until 2025 and had a down year plagued by an injury, but it isn't out of the picture for General Manager Kevin Cheveldayoff to considering trading the young Danish forward.

Younger talent in the system will help offset some losses in the future, as Jack Roslovic, Mason Appleton, and Kristian Vesalainen will boost the forward corps, and Sami Niku will take a major role on defense. Regardless, some changes need to be made as a result of the first round exit, and the cap crunch makes it both easier to make moves, but also more difficult in navigating the future of the team. Fetching a nice return of multiple draft picks and players for Trouba would be nice, but Cheveldayoff could make the decision to pay him the money and let Myers walk in free agency.

The Jets will have lofty goals for next season and beyond, but that will only be possible through tough decisions that await Cheveldayoff and Winnipeg Jets' management this summer.