Time for the snake to shed its skin
Siddartha Guatama, born in India around 500 BCE and who later became known as the Buddha, had a saying that a snake must shed its skin, in order to move on, to leave the past behind. Frankly, for fans of les Canadiens, those words ring true even today (ok that was a stretch).
The Canadiens, under Hughes and Gorton, have certainly parted ways with some of the old culture. They introduced advanced statistics, brought in a specialized trainer, beefed up their scouting staff, and demonstrated far greater corporate transparency. This is all part of this revamped organization's modus operandi. They also acknowledged that the style of play had to change (what blocking shots and relying on a standout performance from your goalie isn't a long-term strategy?). They understand that the only possible route for success (in a flat cap era, and where UFAs tend to avoid Montreal as a destination of choice) is to draft, develop, and empower their young players, in the hopes that in 3-4 years the Canadiens can be a contender. Not for 1 magical spring every decade or so, but more many years. The Boston Bruins and Tampa Bay Lightning are modern-day models of sustainable success.
But in order to fully reach new heights, the Canadiens' brass will also need to shed salary. The Canadiens will finally enjoy some relief this coming offseason as the salaries of Drouin, Byron, Dadonov (hallelujah!) and Sean Monahan (potentially resigning?) will come off the books. But that won't be enough. This snake will need far more shedding.
The Canadiens will undoubtedly need to move some other veterans. The tricky part will be determining how many you want to keep around to properly surround all this budding young talent (now and likely coming in the next two seasons). Anderson, Allen, Hoffman, Dvorak (please trade him), Edmundson, Matheson, and heck even Jake Evans will all have to be evaluated properly, and the sooner the better. Do they have value on the market? Will they still be able to perform at a high level when the Canadiens will hopefully be a contending team? I personally believe this season has given us some answers already (hint: I would move most of them if possible). Gallagher, another unfortunate signing by the Bergevin era, is here to stay, as it's unlikely the Canadiens will be able to find a taker for the valiant warrior.
Until then, the Canadiens may struggle to find enough space to sign their young core, and potentially have to forego opportunities to sign free agents (that would have better complementary qualities to the said core).
Bergevin clearly left the current management with a messy situation. But if there is one duo that may be up to the task of cleaning things up, it's Kent and Jeff. I have full faith in their ability to negotiate fair contracts, as well as their ingenuity when it comes time to move overvalued players for a solid return (see Romanov for Dach). Unfortunately, fully replacing this snake's old skin will take a considerable amount of time.