Looking at how teams have been compensated for taking on bad contracts

The discussion around the Oilers potentially acquiring Duncan Keith ripped Edmonton in half over the weekend.

There are multiple layers to the Keith talk. Some are excited about the idea of the Oilers adding a quality veteran to their roster while others don’t believe he still has the gas to compete at the NHL level. Beyond that, there’s also the entire thing about the cost of acquisition. Is Keith an asset to the Oilers? Is he a cap dump for the Hawks? Are the Oilers going to get a sweetener for taking him on? Will the Hawks take back another contract?

Personally, I don’t hate the idea of adding Keith to play on the team’s third pairing and serving as a mentor for Evan Bouchard. That said, if the Oilers are going to acquire Keith to play in that role, he simply can’t just come in as an added $5,538,462 of expenditure for two seasons.

In order for this trade to make sense, Chicago would ideally take on a bad contract from the Oilers. The top option is obviously @James Neal because the contracts are essentially a wash. But the Blackhawks’ goal here is to free up cap room in order to make a big off-season move, such as adding Seth Jones, so doing a one-for-one, change-of-scenery deal for Neal doesn’t really add up.

With Chicago’s plans in mind, a Keith to Edmonton deal would likely be viewed as a cap dump for the Blackhawks. That would mean they’re looking to move Keith without retaining a major chunk of his cap hit or taking on a big cap hit in return. If the Hawks are looking to dump this entire contract, Edmonton should be asking Chicago for a significant sweetener in exchange for their help.

Here is a list of situations from the past five years in which one team attached draft picks and/or prospects to an albatross contract in order to free up cap room…

As a note, I avoided talking about situations in which the Golden Knights flexed their financial flexibility back in 2017 because the Oilers aren’t an expansion team and the context is very different. Also, I avoided the multiple situations in which players like Marian Hossa, Chirs Pronger, and Pavel Datsyuk were moved as just cash contracts because the Oilers won’t be stashing Keith on the LTIR like those players were.

There have been a couple of instances of such trades in the COVID-era. One was Tampa moving a couple of smaller contracts to Ottawa in exchange for a pair of LTIR deals that they could bury and paying a second-round pick to do so. The other was the Rangers attaching a second-round pick for Detroit to take on the final year of Marc Staal’s deal.

Other examples from a few years back are Montreal and Toronto taking on Steve Mason and Brooks Laich and getting prospects Joel Armia, Connor Carrick, and some draft picks as a reward for doing so. Colorado also took on Brooks Orpik, who they immediately bought out, in order to lower the price of acquiring a quality goaltender in Phillipp Grubauer to just a second-round pick.

The one deal that really stands out here is the price that Kyle Dubas paid to get rid of Patrick Marleau. The Leafs were in a very, very tight cap bind with Mitch Marner as a restricted free agent and badly needed to get rid of Marleau’s $6,250,000 cap hit. Carolina bought out Marleau and ended up drafting Seth Jarvis No. 13 overall in 2020 for their trouble.

Now, there’s obviously going to be some different perspectives on how the likes of Staal and Marleau compare to Keith. Marleau was coming off a fairly productive 37-point season and only had one year left on his deal. Staal had terrible underlying numbers for the Rangers playing a third-pairing role but also only had one year left on his deal.

With Keith, you have a defender who got caved in playing first-pairing minutes on a bad team. There’s reason to believe he can better playing in a less demanding role on a stronger team but he also has two years left on this contract. He also has a no-movement clause, can essentially pick where he goes, and can make life more difficult for the Hawks at the upcoming Expansion Draft.

With that in mind, perhaps Boston and Anaheim’s trade involving David Backes back in February of 2020 could be the template. Boston attached a first-round pick and a prospect to get rid of a year-and-a-half of Backes at $6,000,000 but received a quality player in Ondrej Kase in return.

Something similar here would be Edmonton taking on all of Keith’s contract along with the team’s first-round pick at No. 12 overall while sending Caleb Jones back to Chicago. It isn’t a perfect comparison, of course, but that’s something I would hope Holland is looking at as a reward for taking on Keith.