The Montreal Canadiens are in the thick of their rebuilding process. Last season saw them embrace a bit of a youth movement, breaking camp with four rookies on their roster. Things didn't go well for Montreal at all, but that's a product of the rebuild.

Montreal made headlines with one major move this summer. They involved themselves in the Erik Karlsson trade as a third-party broker between the San Jose Sharks and Pittsburgh Penguins. The Canadiens also went out to acquire a potential future piece in Alex Newhook from the Colorado Avalanche.

The Canadiens kick off their 2023-24 regular season on October 11 with an Original Six matchup. Montreal heads to Toronto for a date with newly-extended Auston Matthews and the Maple Leafs on the road. Montreal then heads home on October 14 for their home opener against the Chicago Blackhawks.

Prior to this, though, the Canadiens have more offseason work to do. And thanks to the Erik Karlsson trade, the Canadiens actually have a logjam they need to sort out before puck drop in October.

Goaltending logjam

In the Karlsson trade, Montreal acquired goalie Casey DeSmith and defenseman Jeff Petry from the Pittsburgh Penguins. Petry has since moved on, heading home to the Detroit Red Wings via trade. However, DeSmith remains with the Habs.

DeSmith is one of four goalies in the Canadiens organization with NHL experience. Jake Allen is the most experienced of the group and Montreal's probable top choice in goal. Behind him, you have Sam Montembault and Cayden Primeau.

DeSmith and Allen bring the most experience, but they also bring the most value in the trade market. Both goalies can do a solid job as a backup option, especially on a contending team. That said, Montreal can't part with both of them.

The Canadiens need to keep one of DeSmith or Allen to be their starter. Montembeault can step in as the backup, with Primeau stepping up when needed. And it is rather obvious who the choice should be.

Montreal's ideal trade

The Canadiens must trade Casey DeSmith. This is crystal clear, but worth talking about anyway. DeSmith is a very solid goalie, and he should find a home somewhere. But Allen has spent the last three seasons in Montreal and is clearly highly valued by the organization.

The trouble with this deal is the lack of a clear market. Sure, there are teams around the league that could use a better backup. Or even just a veteran option in goal. For instance, the Buffalo Sabres could use a veteran to backup and mentor Devon Levi this upcoming season.

However, teams in need of a backup goalie are likely hesitant to pay what it costs to trade for one. Take the Tampa Bay Lightning as an example. They signed Jonas Johansson to a contract worth $775K a year. Why trade for DeSmith and his $1.8 million cap hit if you can get serviceable play from a cheaper and younger option?

The Canadiens could retain salary if they want to maximize their return. However, it's hard to imagine they'll use a valuable salary retention slot to entice a team to take a backup goalie off their hands.

So, yes, there are obstacles here. And Canadiens fans should keep this in mind as this situation unfolds. But if Montreal can trade DeSmith, it might be the best way for the team to clear up their goaltending logjam ahead of the new season.