Frank Seravalli dropped his ‘10 Buyout Candidates’ list on DailyFaceoff.com earlier today and Edmonton Oilers forward @Zack Kassian was listed at number one on that list. Now, most Oilers fans cringe at the idea of the team using a buyout to create cap space and you can’t really blame them. 
If you head over to the Oilers cap page on whatever site you prefer to use, you can see that next season they’ll still be using $1.5 million of cap space on @Andrej Sekera and they have three more seasons of a $1.9 million cap hit because of the James Neal contract. Dead cap space is super frustrating to have to look at, especially in the latter years of a buyout like with Andrej Sekerka, but that doesn’t mean that buying out Zack Kassian is automatically a bad idea.
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It should be considered the last resort option though. First, they should try to trade him straight up with all his cap-hit. Kassian will get another contract in the NHL this summer if he’s bought out so maybe you could entice another GM to bite on his deal just for the sake of taking a chance on the guy. That seems highly unlikely.
More likely, the Oilers will do something like retain $1 million of his cap hit to try and move him to a team that would only have to pay him $2.2 million. @Ryan Reaves was dealt last summer for a third-round pick and his cap hit was $2.3 million. Retaining money is almost always better than buying a guy out because the damage of dead money doesn’t last as long.
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The Oilers could also look to flip Kassian to another team for an equally bad contract but I don’t like that plan. The Oilers need to free up cap space to sign their pending RFA forwards, sign @Brett Kulak, and potentially get a new starting goaltender. They can’t do that if Kassian is just flipped for another bottom-six forward making around $3.2 million.
They could also attach a pick or a prospect to a trade order for the other team to take on his entire deal. The only problem there is that the Oilers don’t have a second, third, or fourth-round pick in this year’s draft and that’s the range of picks teams would likely ask for in return.
They do have picks in the first three rounds of the 2023 draft, but wouldn’t those be more useful at next year’s deadline when the team will hopefully be going all-in for a Stanley Cup run? I think so.
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Kassian is the type of player that an old-school GM would probably value, so there is a chance that Holland moves him, but his contract is so ugly that I’m not sure if there is a team that would even take the forward for free. You’d probably have to attach a pick or prospect to the deal and at that point, depending on the price obviously, it might be better just to buy him out.
A buyout is the most likely option and it’s actually a pretty good idea.
Obviously, if you can trade him with his full salary or by retaining around $1 million, you do it. No brainer. But I’m not sure that’s going to be possible and honestly, the buyout structure for Kassian isn’t that bad.
If GM Ken Holland pulled the trigger on it this summer, it would save the team $2.53 million this coming season. Next season, it would only save them $1.3 million and then for the following two seasons, when Kassian’s contract would have come off the books, there would be a cap hit of $966k.
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It would give them a solid chunk of money to play with this summer and then the Oiler’s cap situation gets a little bit easier going forward. 
Next summer, they’re projected to have $26.1 million in cap space with the Sekera buyout and the money they retained on the Lucic contract coming off the books. The only key piece they’d have to sign next summer is @Evan Bouchard. Now, obviously the deals they sign this summer (Kulak, Puljujarvi, McLeod, Yamamoto, and a goalie) will eat into that, but the Keith and Klefbom deals expiring would give them some wiggle room. Having a little bit more dead money that summer isn’t the end of the world.
Also, with some solid forward prospects in their system (like Holloway and Bourgeault), it’s fair to expect that the Oilers will have some good, cost-effective top-nine players on the NHL roster over the next two or three seasons. Again, that would help with a cap crunch and makes the idea of buying out Kassian more palatable. 
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I’m not of the belief that Kassian is a useless player. He’s not. But he’s far from worth his $3.2 million cap hit and if you can’t find a team that’s willing to take it off your hands and if the price to convince a team to take him is too high, then you have to buy him out. The Oilers have a lot that they need to get done this summer and if you need to bit the bullet on a Kassian buyout to make sure you have the money to sign someone like a Brett Kulak or make sure you can sign all three of your RFA forwards, then you have to do it.