I think the question to ask is why did PLD get moved down in the lineup with multiple teams? Was it because of his lack of effort? The guy has failed now with three different teams. That's too much of a red flag for me.
The Habs are finally down to just two boat anchor contracts in Gallagher and Anderson. Adding seven years of another just doesn't seem wise in order to get rid of one of those shorter term anchors, when there are other options for each of them. Gallagher was fine in the 2nd half of last season, so he should be okay (if overpaid) in a bottom 6 role for at least next season -- and maybe two more. That gets him to a point where a buyout becomes an option. As for Anderson, if a buyer cannot be found and he doesn't improve his play, he could be buried in the AHL to free up an NHL roster spot when it is needed, and save a little on the salary cap until a buyout makes sense. It's not ideal, but better than taking on 7 years of PLD, IMO.
It comes down to how you want to evaluate the risks for each player. Dubois was not moved down the line-up that much with multiple teams. It's a different circumstance with each of the Blue Jackets, Jets, and Kings.
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With the Blue Jackets, it got sour once he demanded a trade. Prior to that, he was performing very well. Remember, Torts was his coach when he wanted out. Torts probably took it personal that he wanted out.
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With the Jets, he was always in their top 6. He performed well when playing with talent. Wasn't horrible when he didn't play with Connor either. Just not a pt/game player when he did.
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With the Kings, they signed him for a big deal and paid a big price to get him when their center depth was already strong. I thought they might play him on wing but they decided to play him 3C with not so much talent.
Gallagher at $6.5M for 3 years:
* Buy him out at some point
* Trade him at a later date and might have to pay a future
* Just let the 3 years pass by and he expires like Drouin
Anderson at $5.5M for 3 years:
* Buy him out at some point
* Trade him at a later date and might have to pay a future.... if he doesn't rebound.
* Just let the 3 years pass by and he expires like Drouin
Dubois at $7M or $7.5M for 7 years (I would not do this deal unless there was retention where he is below Suzuki)
* Don't trade for him and deal with Gallagher/Anderson for 3 more years
or
* Trade for him and trust that MSL and our young core gets him going and motivated. He's still a young player. We end up adding a top 2C who can also play wing and at $7M or $7.5M in a growing cap to come (call me crazy but ends up a value contract). Opportunity capitalization on a player that has wanted to play for Montreal since he asked out of Columbus but other teams kept intervening.
Excuses/context can be made for each player's trend and how they are overpaid. The main risks here are the extra 4 years from Dubois at age 29-32. What version of Dubois do we get.