Following the elimination of the Winnipeg Jets from the 2023 Stanley Cup Playoffs, the team now faces a significant number of crucial decisions. The aging of core veterans, including Blake Wheeler and Mark Scheifele, both of whom become unrestricted free agents at the end of next year, presents a considerable challenge. Additionally, the highly sought-after goaltender Connor Hellebuyck has only one year remaining on his current deal, and at 29 years old, he is carefully considering his future and whether Winnipeg is where he wants to be.
As a starting goaltender, Hellebuyck is well aware of the limited time he has to achieve his goal of winning the Stanley Cup. If the Jets cannot avoid a rebuild of some sort, it is doubtful that Hellebuyck will remain with the team. It will be crucial for the organization to make some significant moves before next year's deadline to avoid losing key players like Wheeler, Scheifele, and Hellebuyck for nothing. However, this may put the team in a difficult position if their aim is to win immediately. Therefore, an intriguing offseason is expected in Winnipeg.