Is Phil Kessel’s Return To Boston Possible?

Well this would be an interesting story, wouldn’t it?

Everyone remembers the trade that brought Phil Kessel to the Toronto Maple Leafs. On September 18, 2009, the Leafs sent their 2010 and 2011 first-round picks, along with a 2010 second-round pick to the Boston Bruins. Those picks became Tyler Seguin, Dougie Hamilton and Jared Knight, respectively.

Tyler Seguin (Bruce Fedyck-USA TODAY Sports)
Tyler Seguin (Bruce Fedyck-USA TODAY Sports)

The Bruins won a Stanley Cup in Seguin’s rookie season. However, they grew tired of his off-ice antics and traded him to the Dallas Stars. Hamilton has played the last three seasons with Bruins but is a restricted free agent come July 1. He is one of the most talked about players in the terms of players that could get an offer sheet. Knight never played a game for the Bruins and was traded to the Minnesota Wild at the trade deadline this season.

Kessel, on the other hand, led the Leafs in goals each year since the trade until this past season. It’s fair to say that the Leafs pretty much won that trade.

However, Joe Haggerty of CSN New England followed up on Bob McKenzie’s report that the Bruins are on Kessel’s list of eight teams he’ll accept a trade to. So now you have to wonder: Could the unthinkable happen?

Haggerty says the the “kneejerk answer” is : “Not a chance.” Of course, that doesn’t stop him from going deeper into the possibility. He points that the 25 goals, a down year for Kessel, would still have led the Bruins. He also said Kessel is a true top-line right winger, something that David Pastrnak and Brett Connolly aren’t ready for.

The Return

When it comes to a return, Haggerty says that it would start with the Bruins 14th overall pick in this year’s draft. He also a points out that some combination of Malcolm Subban, Reilly Smith, Loui Eriksson and Joe Morrow might also need to be involved in addition to draft picks.

It would be interesting if Eriksson, Smith or Morrow were involved as they are three-fourths of the return that Boston got when they sent Seguin to Dallas. Eriksson would be obviously a cap dump in this case, which is something that will be involved in any Kessel deal. Smith and Morrow are both young and would both be good pieces for Toronto’s rebuild. Haggerty also points out that the Bruins might want Toronto to retain as much as half of Kessel’s $8 million cap hit.

The more salary Toronto retains, the better the return will be. However, if the Leafs were to take Eriksson, they probably wouldn’t be retaining half of Kessel’s salary. The problem is that Eriksson is only signed for one more year, so the dump is only effective for next season. For this trade to be made, it’s pretty much a given that Milan Lucic would have to be moved. Taking on Kessel’s full contract would put them over the salary cap right now. Other moves would have to be made as well, possibly a Zdeno Chara trade. On top of all that, there is that tiny matter that the Bruins also have to re-sign Hamilton.

(Tom Szczerbowski-USA TODAY Sports)
(Tom Szczerbowski-USA TODAY Sports)

With the way things ended up in Boston the first time, it would be considered shocking for him to go back. He had issues with Claude Julien, who is still the Bruins’ head coach, over weight issues. The Bruins couldn’t come to an agreement when Kessel became an RFA, leading to the trade.

For the Leafs however, the Bruins would be a good trading partner. They have some young prospects that they could part with. Acquiring the 14th overall selection would give them three picks in the first round (4th, 14th, 24th). If we’ve seen a trend with rebuilding teams lately, it’s that at least once, they have a draft with three first-round picks. Calgary and Columbus did it in 2013 and Buffalo would have done it this year had they not traded St. Louis’ pick to Winnipeg. With the draft as deep as it is, this would be a good year to do that.