Five months after the Montreal Canadiens reached the 2021 Stanley Cup Final, they find themselves near the bottom of the NHL standings. Injuries to core players Carey Price and Shea Weber, the departures of veteran leaders Phillip Danault and Corey Perry via free agency and a shortened offseason contributed to their disappointing performance thus far.

General manager Marc Bergevin and assistant GM Trevor Timmins paid the price by being relieved of their duties in late November. Jeff Gorton, the new executive vice president of hockey operations, will take care of management duties until a new GM is hired.

With the hope of reaching the 2022 playoffs all but dashed, the Canadiens could become sellers by the March 21 trade deadline. Pending unrestricted free agents such as Ben Chiarot could be shopped for draft picks or prospects. Veterans with time remaining on their contracts, such as Jonathan Drouin or Tyler Toffoli, could also be peddled if Gorton and his new general manager decide a rebuild is in order.

Speculation could arise over whether core stars such as Price or Brendan Gallagher will also hit the trade block. The long, expensive contracts of these 30-or-older players could prove difficult to move during the season when teams have limited salary-cap space. Those types of deals tend to occur in the offseason when most teams have more cap room and flexibility.

Talented young players such as Nick Suzuki and promising ones such as Cole Caufield and Alexander Romanov could also draw interest from rival clubs. Those players, however, are unlikely to be moved, as they'll form the foundation of a roster retool or rebuild.

So, which players could the Canadiens attempt to move before the deadline? What type of return could they get, and which playoff contenders might be interested? That's what we'll attempt to determine with this listing of possible win-win trade scenarios for the Canadiens and the clubs they could deal with. Feel free to express your thoughts on this topic in the comments section below.


Jake Allen to the Pittsburgh Penguins

Acquired from the St. Louis Blues in September 2020, Jake Allen was brought in as the backup goaltender to Carey Price. He's done a solid job in that role—so much so that Price waived his no-movement clause to protect his understudy from being selected by the Seattle Kraken during their expansion draft last July.

The 31-year-old Allen has done an admirable job in a difficult situation this season filling in for the sidelined Price. His record of five wins, 15 losses and two overtime losses with a 3.10 goals-against average is attributable to the porous team defense in front of him. His overall career stats (164 wins in 321 starts, 2.56 goals-against average, .911 save percentage, 23 shutouts) demonstrate his value as a solid netminder.

Perhaps the Pittsburgh Penguins will come calling. Allen's reputation as a reliable backup with just a $2.9 million annual cap hit through 2022-23 should be enticing for clubs in need of goaltending depth. The extra year on Allen's contract would also make him a worthwhile pickup.

Penguins starting goalie Tristan Jarry is enjoying a solid bounce-back performance from a difficult 2020-21 season with a 14-5-4 record in 23 games, 1.92 GAA, .933 SP and three shutouts. Backup Casey DeSmith, however, has just two wins in six appearances with a 3.04 GAA, .905 SP and one shutout. They need a more experienced netminder to ease some of Jarry's workload.

Price is working his way back from offseason knee surgery. He's not expected to return before Christmas and seems more likely to make his season debut sometime in January.

Once Price is back in the lineup, the Canadiens should give serious thought to shopping Allen. Even if Price returns to his usually stellar form, it won't be enough to overcome his club's deficit in the standings. They already have Samuel Montembeault backing up Allen, and he can remain in that role for the rest of the season.

The Canadiens gave up a third-rounder and a seventh-rounder in the 2020 NHL draft for Allen, and they could request a third in the 2023 draft and a seventh in this year's draft. If that's not feasible, they could seek a second-rounder.


Ben Chiarot to the New York Rangers

Ben Chiarot's play is among the few bright spots for the Canadiens this season. He's been their most reliable defenseman thus far with a team-leading 23:30 of time on ice per game and 2:47 of shorthanded ice time per game. The 6'3", 234-pounder is also among their leaders in hits (65) and blocked shots (52).

As an unrestricted free agent in July, Chiarot should attract interest from contenders as the trade deadline approaches. His size, defensive style and ability to log big minutes are attributes that come in handy during the postseason when the emphasis is on rugged shutdown hockey.