McDonagh, R ($2,350,000 retained)
Additional Details: Ok, I know this one will draw criticism right off the bat. Sergachev has been amazing and could be big part of future for bolts. But as of recently Lightning have struggled a little bit. With a good a team as theirs, they're going to clearly be buyers at the deadline. But trading sergachev makes sense for two reasons, the first being their struggles recently. No matter how you slice it, putting trust into a 19 year old on any pair no matter how good they have been is risky in playoffs. McD is a proven commodity who can put them over the top. But the bigger reason is the amount of paydays that the lightning are going to have to give out. Kucherov, Point, Vasilevskiy, and Namestnikov are big names that deserve more money (although I could see him being dealt). Johnson Palat Killorn and Callahan also take up a large chunk of space, along with Stamkos and Hedman (those are no brainers). And even with expiring deals coming up in the next year such as Stralman, sustr, and Girardi, it's not going to be enough. It's going to be difficult to pay all of the guys who need paydays, and something is going to have to give. Even if Namestnikov is traded, it will still be difficult to keep it under the cap. And there are plenty of prospects coming up that can fill roles in the next year or two. Give up Sergachev now, and while its a lot to stomach, getting a first pair defenseman for two seasons at reduced salary (not sure if that would have to be half) is a pretty good deal.
Some of those guys are a long way off from pay raises, but eventually they will hit, and the big contracts no one wants are going to be there.