Toronto Maple Leafs Trade Tree: Phil Kessel

The Pittsburgh Penguins are an offensively gifted team, and this goal is a prime example of their depth as Phil Kessel and Patric Hornqvist hook up for an amazing and possible goal of the year candidate.

Phil Kessel is a Stanley Cup Champion.

We know that much about the second-best Kessel but a lot happened to him before he raised Lord Stanley’s mug.

Considering how many of these trade trees I’ve made this season, it’s surprising I haven’t gotten around to Phil Kessel coming to or leaving Toronto yet. So you know what?

Let’s do both!

The Leafs’ acquisition of Kessel from the Boston Bruins was debated for over half a decade and trading him to the Penguins showed immediate results for Pittsburgh. Let’s look at how the Phil Kessel trades, both of them, have impacted the Toronto Maple Leafs, Boston Bruins, and Pittsburgh Penguins.

Let’s begin with Kessel coming to the Leafs.

Surely you know the trade by heart now. It took place on Sept. 18, 2009 and was dissected until the Bruins traded Tyler Seguin in July 2013. After that, the trade was only beaten to death sometimes, along with the new Seguin-for-Eriksson deal.

Part of what had plagued the Leafs prior to the “Shanaplan,” was their blatant disregard for learning from past franchise mistakes involving trading away high draft picks.

In 1989, Leafs GM Floyd Smith traded Toronto’s first-rounder in 1991 to New Jersey. The 1990-91 Leafs stunk, the pick was third overall, and the Devils selected Scott Niedermayer. Boo.

In 1996, Leafs GM Cliff Fletcher traded Toronto’s first-rounder in 1997 to the Islanders. The 1996-97 Leafs stunk, the pick was fourth overall, and the Islanders selected Roberto Luongo. Boo.

The fatal error the Leafs made in those two deals was they traded away a future first-round pick not knowing how high in the draft it would be.

So, what did the Brian Burke Maple Leafs learn from those two trades? Nothing!

In Sept. 2009, Burke acquired Kessel from the Boston Bruins for a 2010 first, 2010 second, and a 2011 first.

Kessel led the Leafs in scoring in all six seasons he spent with Toronto. The Bruins of course, picked Tyler bleep-bleep-bleeping-Seguin second overall.

Seguin contributed seven points in 13 playoff games in 2011, the Bruins won the Cup, and then Seguin and fellow Bruins rookie Brad Marchand painted Boston shirtless.

The Bruins then signed Seguin to a spectacular deal in September 2012: Six years at $5.75 million per season. Given what some centres in the league make today, and knowing what kind of star Seguin would blossom into, Seguin’s contract might be one of the best in the league.

Which is why it’s hilarious the Bruins sent him to Dallas in July 2013 before the extension even kicked in.

But wait, there’s more.

The Leafs didn’t stink as much in 2010-11, but they still stunk a little. Enough anyway to allow the Bruins to pick Dougie Hamilton ninth overall with the second first-rounder they owed them for Kessel.

But once again, the Bruins decided to trade a budding star as soon as his entry-level contract expired.

The Bruins traded Hamilton to Brian Burke’s Calgary Flames, in exchange for a 2015 first-rounder and two 2015-second-rounders.

Now, it’s too soon to fully judge this trade. The 2015 first-rounder was used to select Zachary Senyshyn, who is a goal-scoring monster in the OHL. The first 2015 second-rounder was used to pick Jakob Forsbacka-Karlsson, who was third in scoring on Boston University this past season. The other 2015 second-rounder was used on defender Jeremy Lauzon, whose production with the QMJHL’s Rouyn-Noranda Huskies seems to have taken a step back this season.

In total, from the Bruins’ side of the Kessel trade tree, Boston got 1,004 NHL games, 195 goals, 295 assists, and 490 points. Kessel provided the Leafs with 446 NHL games, 181 goals, 213 assists, and 394 points on his own.

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There’s a case to be made that Kessel is far and away the best player involved in this deal. After all, the Bruins traded Tyler Seguin away before he had a chance to become Tyler Seguin. You could also say Boston squandered two top young talents in this league by trading them away early.

In defence of Boston, did they not win a Cup in 2011? Did they not come within two wins of another Cup in 2013? The Bruins were a contender paying lots of star players – Zdeno Chara, Patrice Bergeron, David Krejci and Tuukka Rask a huge sum of money. Kessel was dealt because Boston needed cap room. Same with Seguin and Hamilton.

If you haven’t before, you must watch this video of the 2013 Boston Bruins braintrust discussing the prospect of trading Seguin. The video features current Oilers GM Peter Chiarelli, current Canucks GM Jim Benning and current Bruins GM Don Sweeney. Get ready for some Seguin opinions that have aged like a bag of milk in the sun.

The Bruins got a lot for Phil Kessel, squandered a lot of it, still have some prospects who might turn out great, and have a Cup to show for it. Meanwhile the Leafs gained one of their best wingers in franchise history during one of the worst eras in franchise history.

Kessel’s off-ice moments in Toronto were plentiful.

Like that time he called a reporter an idiot.

That along with the ridiculous hot dog story, that time he got picked last at the 2011 NHL All-Star Draft, and countless other things, Phil’s time in Toronto was colourful. Ultimately, it was an era wasted.

One more thing: Name a Leaf who was better than Phil Kessel during his six seasons in Toronto.


Six years pass by, the Leafs stink but at least had the sense to keep their first-rounder, the “Shanaplan” is implemented, and the rebuild begins.

But before the rebuild came the de-build.

The Leafs managed to miraculously trade David Clarkson and Dion Phaneuf without retaining any salary. They weren’t so lucky with Phil Kessel.

With the Penguins looking to add Kessel but with little cap space to spend, salary had to be retained for a deal to get done. And the deal did get done with Toronto retaining $1.2 million per season until 2021-22.

On July 1, 2015, less than two years ago, the Leafs dealt Phil Kessel, forward Tyler Biggs, defender Tim Erixon, and a 2016 conditional second-rounder to Pittsburgh in exchange for forward prospect Kasperi Kapanen, defensive prospect Scott Harrington, forward Nick Spaling, a 2016 conditional first-rounder, and a 2016 third-rounder.

A couple notes about the picks:

• The 2016 second-rounder that Toronto gave Pittsburgh was actually given to Toronto by Pittsburgh the season before in exchange for Daniel Winnik, who the Leafs had re-signed, and later re-traded, anyway. Basically the Leafs gave the Penguins their pick back.
• The 2016 first-rounder the Penguins gave the Leafs was conditional on the Penguins making the 2016 Stanley Cup Playoffs. Remember last Christmas when it didn’t look like the Penguins would make the playoffs and the Pens fired their coach? Life comes at you fast.

We all know the juicy stuff here.

Kessel led the Penguins in playoff goal-scoring with 10 goals, 22 points, and would have won the Conn Smythe Trophy if it weren’t for that Sidney Crosby guy.

Biggs and Erixon were essentially roster spot dumps. With the 2016 second-rounder, the Penguins selected Finnish winger Kasper Bjorqvist 61st overall. He has nine points in 30 games for Providence College this season.

The Leafs’ return is still developing.

Kasperi Kapanen scored 43 points in 43 AHL games this season despite missing time with a lower-body injury. In limited NHL time, Kapanen has played on the fourth line and penalty kill for Mike Babcock.

Scott Harrington began last season in the NHL but ultimately lost the season due to injury. At the 2016 draft, the Leafs dealt Harrington to Columbus for former first-rounder Kerby Rychel. In 68 AHL games this season, Rychel has 19 goals, 31 assists, and 50 points.

The 2016 third-rounder the Leafs got from Pittsburgh was used to select American defender J.D. Greenway. He only had seven points for the University of Wisconsin this season. He’s also listed at 6-foot-4 and 205 lb.

Nick Spaling was mostly a salary dump for Pittsburgh but played 35 games for his boyhood team. The Leafs also sent Spaling to San Jose who lost to Kessel’s Penguins in the Stanley Cup Final.

“Why isn’t the Spaling trade in the trade tree?” It’s not exactly “The Spaling Trade” now, is it?

It was for Roman Polak. The San Jose Sharks acquired Polak and Spaling from the Leafs for a second-rounder in 2017, another second-rounder in 2018, and Raffi Torres’ contract. Spaling seemed like an add-on to the trade rather than the principal part.

The Leafs traded their 2016 first (the one that wasn’t used to select Auston Matthews) and a 2017 second-rounder to the Anaheim Ducks for Frederik Andersen, who many have argued has been the Leafs’ MVP this season.

Finally the Phil Kessel trade tree to and from Toronto is done… for now.

I believe you can’t lose a trade if the result is a Stanley Cup win. Less than two years after trading Kessel, the Bruins won the Cup. Less than one year after acquiring Kessel, the Penguins won the Cup.

As for the Leafs, well…

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