Grading the Toronto Maple Leafs Most Notorious Canada Day Moves

MONTREAL, CANADA - MARCH 3: Toronto Maple Leafs General Manager Brian Burke speaks to the media during a press conference to introduce new head coach Randy Carlyle at the Bell Centre on March 3, 2012 in Montreal, Quebec, Canada. (Photo by Richard Wolowicz/Getty Images)
MONTREAL, CANADA - MARCH 3: Toronto Maple Leafs General Manager Brian Burke speaks to the media during a press conference to introduce new head coach Randy Carlyle at the Bell Centre on March 3, 2012 in Montreal, Quebec, Canada. (Photo by Richard Wolowicz/Getty Images) /
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Phil Kessel, Toronto Maple Leafs
Phil Kessel, Toronto Maple Leafs (Photo by Bruce Bennett/Getty Images) /

2015: The Penguins Get Some Thrill

After being a rocky team over the past couple of seasons, then Interim GM Kyle Dubas pulled the trigger on one of the biggest trades we have seen in a while.

To help the Toronto Maple Leafs head into a rebuild, they dealt star winger Phil Kessel, 2011 first-rounder Tyler Biggs, journeyman Tim Erixon, a 2016 second-round pick, and retained $1.2 million per year for the remaining seven years of Kessel’s contract. Whew.

Heading to Toronto was 2014 first-rounder Kasperi Kapanen, defensive prospect Scott Harrington, depth forward Nick Spaling, and a first and third-round pick in the 2016 NHL draft. If that’s hard for you to read, here you go.

Kessel would put up 303 points in 328 games and won back-to-back Stanley Cups in ’15-’16 and ’16-’17. That alone wins the trade for the Pens, but that’s not to say the Leafs lost.

Biggs and Erixon would not play one NHL game in Pittsburgh, and the second-rounder drafted forward Kasper Bjorkqvist. He has yet to solidify a roster spot in the AHL. Kapanen would become one of Toronto’s budding stars, putting up 80 points in his last 147 games with the team before being traded back to the Penguins. He along with Pontus Aberg and Jesper Lindgren gave the Leafs a 2020 first-rounder, Filip Hallander, David Warsofsky, and Evan Rodrigues.

Harrington split time between the Leafs and Marlies for one season before being traded to the Colombus Blue Jackets. Heading to Toronto was depth forward Kerby Rychel.

Spaling was a depth option in Toronto for the ’15-’16 season but got traded to the San Jose Sharks right after. That trade also included Roman Polak and gave Toronto two second-round picks and Raffi Torres.

The 2016 first-rounder got traded to acquire Frederik Andersen, and the third-rounder drafted James Greenway. At 23-years old, he still plays in the NCAA.

The $1.2 million retained on Kessel’s contract is still against Toronto’s cap, but it will expire after this season. With that, the Leafs will no longer have any direct ties to the blockbuster trade.

While the Pens benefitted by winning two cups, the Leafs benefitted by accelerating their rebuild. Kapanen and Andersen (from a trade using the 2016 1st rounder) were a part of four playoff runs with the Maple Leafs. The recouped assets from Kapanen’s return to the Pens were also handsome.  Not to mention that without making this trade, the Leafs probably are not bad enough to get the first overall pick and subsequently draft Auston Matthews.

Grade: B+