TLN Roundtable: Should the Leafs Trade Kessel?

It’s been a really, really interesting few days in Leafs Nation. First, we found out that Brendan Shanahan has the blessing of the MLSE Board to strip this team down to the wood and build it up all over again. Then we had the Leafs’ best player, Phil Kessel, tell reporters that he loves Toronto, but “if it’s not here, it’s not here“.

It’s going down, guys. It’s the beginning of the end for this team.

There are, of course, some perceived untouchables. Pretty much everyone agrees that players like Morgan Rielly, William Nylander, and any future draft picks shouldn’t be moved for any reason, while others include Kessel in that group.

We asked the TLN staff to share their opinion on the idea of trading Kessel – here’s what we got…

There are too many “ifs” around the Leafs to even begin entertaining the idea of trading Phil Kessel at the deadline and probably by the draft. While we’ve heard via the questionable source of Cathal Kelly that the Leafs are willing to scorch the earth, some actually evidence of this being put into practice should be seen before pushing Kessel out the door. Who will be the Leafs GM next year? Should Kessel be something that falls on them? Who will the next coach of the Leafs be? Is having a legitimate talent important to attracting a legitimate coach? What of the draft lottery? If the Leafs were to actually win the draft lottery (LOL, yeah right) a Kessel-McDavid combo likely speeds up the rebuilding process enough that you don’t deal Kessel.

The reality is that trade offers on Kessel should absolutely be entertained now, at the draft, throughout the summer, and ongoing until the deal the Leafs want materializes. The interest in adding a 30 goal scorer isn’t going to go away anytime soon, and the Leafs have plenty of time to look for the best return, even though it seems unlikely that any return would be satisfactory when giving up Kessel. Waiting beyond the draft means that the Leafs can seek offers for players they are disappointed to have missed in this draft, and a deal over the summer that would include a 2016 1st round pick means the Leafs can gamble on a deal with a bubble team and hope that team’s pick falls into the lottery. Waiting until the summer also makes the deal less dependent on taking salary back which is nice too. What’s also nice is if the deal doesn’t materialize this summer you probably two more summers to attempt a deal before you start seeing returns for Kessel decline steeply.

The Leafs absolutely have to trade Phil Kessel. That’s not to say I don’t like the guy… the exact opposite, actually. It’s just that if the Leafs want to rebuild – and I mean really, really rebuild, then everything has to go (save for Morgan Rielly, and maybe Nazem Kadri). 

Let’s not kid ourselves and pretend that this team would benefit from a partial rebuild. It’s got to be a full tear down, or Leafs brass is just wasting their time as well as the fans’. And a full tear down means players like Kessel, Dion Phaneuf, Tyler Bozak and (probably) James van Riemsdyk need to be moved. The assets they would bring into the organization, in the form of young roster players, prospects, and draft picks, are vital. It’s that volume of assets that speeds up a rebuild, not keeping one or two of those players and letting them depreciate for several years.

Speaking of the speed of a rebuild, this isn’t going to be a quick fix. You’re looking at three years at the very least to simply start turning things around, and another few years before the youth movement develops into consistent contributors and useful free agents actually want to play in Toronto. While Kessel certainly has a style of play that lends itself to longevity, and while hasn’t battled injuries, a five year rebuild will bring Kessel to age 32. He’s worth more to the team being moved now than he will be in his early 30’s. It’s tough, but he’s got to go.

The Leafs should trade Phil Kessel. If you’re going to do a rebuild, you should do it right. There are a lot of benefits to trading Kessel – the most obvious of which is the 3-4 assets you could get in a return for him. Sure maybe the pieces you get back are more B-level than game-changing, but what they do represent is a step in the right direction.

The Leafs need to restock the shelves full of young talent and trading Phil Kessel provides that opportunity. It also has the added benefit of making your team worse in the short-term, which could help raise the value of the team’s own draft picks. Kessel will be 28 by the time next season starts. For the time being, he’s still an elite winger that has a lot of trade value. It’s possible we won’t be able to say the same thing 3 or 5 years from now. And anyways, what’s the point of keeping him? Unless you win the draft lottery and get Connor McDavid, the team is going to continue to struggle in the standings for at least the next little while. 

The team has already wasted away his prime years, there’s no sense continuing that trend. A proper rebuild consists of accumulating young talent. Trading away Phil Kessel can help accomplish that for the team in a huge way. If you are going to rebuild, Kessel should be among the first to go. The team has set on the fence of mediocrity for too long. The team needs to choose a direction and commit to it with authority. Trading Phil Kessel definitively marks a rebuild and helps the team begin to accomplish its new goals.