Monster trade already brewing between Oilers and Red Wings?

The Edmonton Oilers may not be done reshaping their roster after all and a potential connection with the Detroit Red Wings is starting to attract serious attention.

Edmonton’s goaltending situation remains one of the organization’s biggest concerns heading into the offseason. Tristan Jarry struggled heavily after arriving with the Oilers and still has two years remaining on his contract with a $5.385 million annual cap hit. Meanwhile, both Connor Ingram and Calvin Pickard are eligible to become unrestricted free agents on July 1.

While Ingram could still return on a more affordable deal, uncertainty surrounding the position has fueled speculation that Edmonton may explore the trade market once again.

According to veteran reporter Jim Matheson, moving Jarry would likely require the Oilers to attach a significant asset or absorb another undesirable contract in return. However, another possible route may already be emerging.

During recent discussion surrounding Edmonton’s offseason plans, Oilers insider Bob Stauffer referenced an Eastern Conference team with “four pretty good goaltenders in their system right now.” While Stauffer did not identify the organization directly, we all know the comments were aimed at the Detroit Red Wings.

Detroit’s goalie pipeline is viewed as one of the deepest in hockey, featuring prospects Sebastian Cossa, Trey Augustine, Michal Postava, and Carter Gylander. While top names like Cossa and Augustine are likely untouchable, others in the system could become available if the Red Wings decide to deal from a position of strength.

For Edmonton, solving the crease remains a priority if the team hopes to remain a legitimate Stanley Cup contender. And if the Oilers become aggressive this summer, Detroit could quickly emerge as one of the most intriguing trade partners to watch.