Two players that would be welcomed back to Montreal

Both are battling as part of the Winnipeg Jets in a playoff battle with the Colorado Avalanche. They may take some convincing to come back to Montreal, but it would be a nice reunion.
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Though the Montreal Canadiens have had to depart with certain veterans for the benefit of the current team, there is reason to believe they would be open to a return.

Kent Hughes has done a wonderful job getting the most out of each of his trades. He has also ensured that the player that moves on, gets to join an organization that is a perfect fit. Because of his adept work and gentlemanly conduct, he has kept relationships tightly knit. 

Should the Canadiens feel confident they can make a big push for the playoffs next season, they could consider bringing back some familiar faces. With the Habs top six being quite young, adding an experienced veteran to balance things out could be a smart move. Likewise, should Kirby Dach struggle down the middle, having a centreman to help support him on faceoffs would be a smart play. 

If the Habs did want to shore up their offence with a pair of familiar faces, there’s good reason to believe that the idea isn’t so crazy. Both players are mixing it up in the playoffs right now, so they will have more experience under their belts come July. And the Habs do have some aging players on the roster, but the importance of depth and a strong offence could push certain players down the depth chart or off the team. 

With Joel Armia's improved play towards the end of the season, he could garner some trade interest once the offseason begins. Should he be moved out for a draft pick or prospect, that would free up a spot on the wing. The ideal move would be to promote from within, but bringing in a player with experience would stiffen the competition and give the younger players more time to develop.

Tyler Toffoli is the first guy that comes to mind; in Montreal, Toffoli was a staple in the locker room and he was the perfect mentor for Cole Caufield and Nick Suzuki. Not only does he bring experience, but familiarity and a knack for scoring timely goals. He isn't the most fleet of foot, but in a middle-six role, he would elevate the Habs forward core.

Toffoli is in the last season of his current deal, so at the season's end, he is free to sign wherever he wishes. Because Winnipeg is currently a contender, there is a logical reason to believe that he will re-up with the club. However, I wouldn't be too surprised if Hughes tendered the unrestricted free agent some sort of offer.

Sean Monahan, is perhaps the least likely of the two, simply because the Canadiens have Suzuki, Dach, Christian Dvorak and Jake Evans. But, I think if the Habs receive calls for Dvorak, which isn't highly likely, they should move on from him. Monahan, as we all know is a significant upgrade on Dvorak, and he is the type of player that fits wherever he is lined up and makes his linemates better.

Monahan is also in the final year of his current deal, which was for one year; which the Habs signed him to. An unrestricted free agent once the season ends, Monahan will be looking for a new deal and if the expectations are for the Habs to be competitive in 2024-2025, Monahan would be a wise addition. He could slot right in on Dach's wing, which would render the Habs one top-six forward away from having their top two lines well-balanced.

Both players would fit seamlessly into the culture that the Canadiens have formed, and they are known for their clutch, smart play styles.