The Edmonton Oilers' quest to solidify their goaltending situation has led them to the Boston Bruins' Michael DiPietro, but acquiring him won't be as simple as waiting for waivers. With the Bruins facing a crowded crease, a trade is the most likely path for the Oilers to land the promising young goalie.

DiPietro, 26, has emerged as a potential target for Edmonton due to his impressive performance in the AHL with the Providence Bruins during the 2024-25 season, where he recorded a .927 save percentage in 50 games. This performance has made him a popular name among analysts and insiders who anticipate the Bruins might part ways with him.

Boston currently has three goalies in the mix: Jeremy Swayman, veteran Joonas Korpisalo, and DiPietro. Swayman and Korpisalo are aiming to rebound from disappointing seasons, and the Bruins seem inclined to give them that opportunity, potentially leaving DiPietro as the odd man out.

While the Oilers might be tempted to wait for DiPietro to be placed on waivers, that strategy is unlikely to succeed. Due to NHL waiver priority, several other goalie-needy teams would likely claim DiPietro before the Oilers get a chance. Allan Mitchell of The Athletic suggests that DiPietro's strong AHL numbers would make him a hot commodity on the waiver wire, making it improbable he would reach Edmonton.

Therefore, Oilers General Manager Stan Bowman would need to negotiate a trade with Boston to acquire DiPietro. The timing of any potential deal will be crucial, likely occurring late in training camp as the Bruins finalize their roster decisions. The Oilers must avoid waiting too long, which could allow another team to acquire DiPietro, but also avoid acting too quickly and potentially overpaying before the Bruins' goaltending situation is fully resolved.

The Oilers are in search of a reliable goaltender, with some suggesting they should trade Stuart Skinner. A trade proposal even suggested sending Skinner to the Buffalo Sabres for Ukko-Pekka Luukkonen. Cam Talbot of the Detroit Red Wings has also been mentioned as a potential acquisition for the Oilers.

Ultimately, if the Oilers are serious about adding DiPietro to their roster, they will need to pursue a trade with the Bruins. While the waiver wire might seem like an appealing option, it's simply not a realistic path to acquiring the promising young goaltender.