1. Toronto Maple Leafs
The Calgary Flames appeared hesitant to do business with former General Manager Brad Treliving at the trade deadline, but if the Maple Leafs fail to go deep in the Stanley Cup Playoffs this season on the back of poor goaltending, it's time for them to take a massive swing. The Toronto Maple Leafs themselves were hesitant at the deadline, with Treliving wanting to hold onto his 2024 first-round pick and several top prospects, but with the Flames needs for future assets and the Maple Leafs desire to compete right now with a No. 1, this is a match made in heaven.
The Leafs potential interest in Markstrom hinges on their upcoming playoff run, as Joseph Woll appears to be a player of the future, but if they truly want to capitalize on the talents of Auston Matthews, Mitch Marner, William Nylander and their star studded forward group, a deal needs to be made. Pairing that with a potential top free agent signing such as a Chris Tanev would make this team a genuine threat, and if Treliving and the Flames can get past their issues, this is a move that would make perfect sense.