Marc Bergevin is an enigma. Since coming over from the Chicago Blackhawks organization to be the general manager of the Montreal Canadiens, he has made some great moves, and some bewildering ones. If there is one thing I have learned, it is to always expect the unexpected with him.

On July 1, there were reports linking the Canadiens to a number of players. There was not a whisper about Alexander Radulov, and then out of nowhere, reports of a completed deal surfaced. This is but one example in a long line of transactions that came out of left field. Bergevin is a hard man to read.

But that was arguably a very good move, and what could end up defining his tenure will be the head scratchers. The Canadiens were viewed almost universally as a legitimate contender last year until things fell apart, and if they can't get back to that this year, those questionable moves will be viewed under a much brighter light with the added benefit of hindsight.

The unfortunate reality of managing the Montreal Canadiens is that anyone who takes the position is ostensibly held in comparison to the likes of the great Sam Pollock. Big shoes to fill, but that's something one has to know when walking into such a job. If you want to be remembered fondly, you need to win.

Bergevin has been posturing for a Stanley Cup since he took office. He seems to still have the necessary core pieces to get one, but he traded one member of his core for someone he believes will get them closer. He has to win before he's done. Anything less, and he could be remembered as one of the worst general managers in the history of the team.

He signed Carey Price to a six-year deal, and did so at excellent value. He then signed Max Pacioretty to a six-year deal, and, again, got great value. Eventually, he orchestrated yet another six-year deal with Brendan Gallagher, once again at excellent value.

Then there are the gambles. He gambled by signing Alexei Emelin to an extension before his existing deal was up, and while he was coming off an injury, and it backfired. He gambled by signing P.K. Subban to a bridge deal, and you guessed it, that backfired.

He gambled by signing Alex Galchenyuk to a bridge deal, and there will be a tremendous amount of focus on how that situation gets handled at season's end. So far in Bergevin's tenure, the bridge deals have not offered any sort of long-term savings.

Safer gambles like the one-year deal for Alexander Semin, which unfortunately didn't work out, are easy to swallow. The same can be said of the Alexander Radulov deal. Even if Radulov plays terribly, there won't be any long-term consequences.

He may feel comfortable in that foxhole for now, but if things start to go south in 2016-17, the barrage may just land a direct hit

But his biggest, and likely most costly, gamble is of course that Subban for Shea Weber trade. I've talked enough about this deal for my feelings to be well known, so the short form is that he traded away the prime years of Subban for the decline years of Weber. Bergevin needs a Cup win, and soon, if he's to have any sort of vindication on that front.

He had an analytics specialist on staff that advised against the trade, and he didn't listen. He traded away a player that should have been part of the team's core and leadership group for at least the next six years. He traded away one of the more beloved players in recent team history. If it doesn't pay off as he seems to think it will, he's in the crosshairs. He has to be.

Now, he doesn't necessarily need that win this year in order to save his job. However, if they don't make the playoffs, and at least put up a good fight there, I don't see him even getting the chance to see out things like the Galchenyuk negotiations.

Geoff Molson wouldn't have a choice at that point. He has given Bergevin plenty of slack to build his team. To build Michel Therrien's team. If that fails, he has to start worrying about Montreal's team. If the Subban trade is the writing on the wall, we could be looking at a team in three years without Max Pacioretty, Carey Price, and Alex Galchenyuk as well.

Basically the entire core could be gone. Molson cannot, and I hope would not, allow it to come to that. If they aren't right back in the mix next year, there can be absolutely no justifying a situation where he stands pat and allows the management to continue on the path they're on.

He may feel comfortable in that foxhole for now, but if things start to go south in 2016-17, the barrage may just land a direct hit, and he'll be gone.