The Detroit Red Wings are reportedly considering a significant move to bolster their roster and end their playoff drought, which extends back to 2016. General Manager Steve Yzerman may be looking to make a splash this summer through a substantial trade.

A proposed trade scenario has the Red Wings acquiring Winnipeg Jets star winger Kyle Connor. In exchange, Detroit would send Michael Rasmussen, prospects Nate Danielson, Marco Kasper, and William Wallinder, along with a 2026 first-round pick and a 2028 second-round pick to Winnipeg.

Kyle Connor, a Michigan native and University of Michigan alumnus, is coming off a season where he scored 97 points. He has one year remaining on his $50 million contract. Adding Connor would provide a boost to Detroit's offense.

The potential acquisition of Connor isn't surprising, as the Red Wings could aim to secure him before he hits free agency, possibly through a sign-and-trade agreement. However, the puzzling aspect of this trade proposal lies in the hefty return for Connor. If Connor is unlikely to re-sign with the Jets, it might be because he has already communicated his intentions, opening the possibility of him joining the Red Wings in free agency without Detroit needing to give up any assets. A more reasonable approach might involve shedding some salary and offering the Jets a smaller package to secure Connor.

With over $12 million in cap space and a strong prospect pool, Detroit can afford to make a deal, but they could also wait to see if Connor is heading their way regardless.

As of now, there are no reported issues in negotiations between Connor and the Jets. Winnipeg would likely only consider trading him if those negotiations falter.

Other teams that might be interested in acquiring Jason Robertson include the Los Angeles Kings, Carolina Hurricanes, Washington Capitals, Columbus Blue Jackets, Seattle Kraken, and Utah Mammoth.