The Leafs’ worst contract is actually Phil Kessel’s retained salary

Although it feels weird to say this in November, we are well into the dog days of the NHL offseason. Meaning we rarely see much news regarding transactions and announcements (with a few notable exceptions) while waiting for the return of hockey on XX/XX/2021.

It also means sports talk radio shows will look to find any sort of content to keep viewer interest up, leading to stuff like this:

Even if it were true that the Leafs did indeed overspend on @John Tavares, he was a free agent back in 2018 and could have easily accepted the San Jose Sharks’ offer of $13 million per season but instead took less to play for his hometown team. We don’t even need to get into whether or not the Leafs overpaid @Mitch Marner on his extension.

Instead of responding with anger and fury over this take from the OverDrive team, I would like to instead present a counter-argument. As the title of this post outlines, the actual worst contract on the Leafs is @Phil Kessel’s retained salary.

You may recall that Toronto decided to trade the star winger back in 2015 when the team was ready to commit to a full rebuild. It was a curious, yet necessary, move needed despite the fact they had signed him to an eight-year deal at $8 million per season less than two years prior. The problem was that in order for the Pittsburgh Penguins to agree to the trade, the Leafs had to absorb $1.2 million of his salary for the last seven seasons of his contract (year one was the 2014-15 campaign).

It may not have seemed like a big deal at the time, but the implications of Toronto willingly choosing to keep part of his salary on the books continues to hurt the team to this day and it will remain so until his contract expires in 2022.

When the Kessel trade first happened, the Leafs were not thinking about trying to compete for a Cup within the next few years since their focus was on acquiring high-end talent through the draft and begin anew with a different core. The arrivals of Marner, @Auston Matthews, and @William Nylander accelerated their plans and put the team in a spot where they would need to spend their money wisely to maintain the core.

Jump ahead to the present day and the Leafs find themselves over the salary cap by, coincidentally, roughly $1.2 million. For context, @Wayne Simmonds is currently locked for the season on a $1.5 million deal. Had Toronto decided to dump all of Kessel’s salary on the Penguins, they would have shed the equivalent of 80% of Simmonds in freed up salary today!

To be fair, the Leafs would have had trouble getting Pittsburgh to eat up Kessel’s entire contract since they were tight on cap space at the time. Which is why the report that Toronto was apparently keen on maintaining part of his salary in a potential deal seemed shortsighted in the grand scheme of things.

There were plenty of other teams that were reportedly interested in trading for Kessel back in 2015, including the Nashville Predators, Florida Panthers, Philadelphia Flyers, and Calgary Flames. I’m sure at least a few of those teams could have afforded to take on his contract without having the Leafs retain parts of his salary to make a deal happen, so it might have been better for Toronto to wait a bit longer to find a trade partner who could satisfy that. It’s not to suggest getting @Kasperi Kapanen and a first-round pick that turned into @Frederik Andersen was a bad decision, but perhaps they could have gotten a similar type of return elsewhere.

While we’re on the subject, Andersen, @Morgan Rielly, and @Zach Hyman will need new contracts soon and all three will likely command a lot of money either from the Leafs or on the open market. While I don’t think the Leafs should bring Andersen back, it’s not going to be easy to keep him or the aforementioned players on the books due to the team being tight on salary. What’s more is that due to the ongoing COVID-19 outbreak, the NHL is going to be implementing a flat salary cap for the foreseeable future because of lost salary during the forced stoppage. Meaning the Leafs will have little choice but to search for cheaper alternatives to keep the team competitive for the years to come.

All of this stemming from the Leafs choosing to absorb part of Kessel’s salary.

Now that it has been over five years since the blockbuster trade has occurred, it’s safe to say that the Leafs made a big mistake in retaining 15% of Kessel’s contract. The decision put them in a position where they would be tight on cap space for a while, which has been further heightened by a flat cap as the result of a global pandemic. While freeing up a little over a million in salary may not seem like much, it makes a big difference in being able to give marquee players in need of new deals the money necessary to remain a Leaf.

So the next time someone says to you that Tavares’ is the team’s worst contract, don’t give them an incensed response. Tell them that the correct answer is the Leafs paying Phil Kessel $1.2 million a season to play for the Arizona Coyotes.