1. Phil Kessel for Kasperi Kapanen
The Toronto Maple Leafs were involved in two blockbuster trades involving Phil Kessel.
The first was the deal to bring him to Toronto that fell just outside the decade. That transaction spearheaded by Burke brought Kessel to the blue and white in exchange for a 2010 first-round pick (second-overall: Tyler Seguin), and a second-round pick (32nd overall: Jared Knight) along with a 2011 first-round pick (ninth overall: Dougie Hamilton).
The biggest deal of the decade for the Leafs was Kessel’s second trade, the one that sent him to the Pittsburgh Penguins. On July 1, 2015, after six seasons, scoring 181 goals, adding 213 assists for a total of 394 points in 446 games, the Leafs pulled the trigger to ship Kessel out of town.
The trade triggered what was widely considered to be a rebuild for the Leafs.
By moving the sniper, the Buds not only got a decent return, but also freed up cap space, which also has significant value in the NHL. Ahead of the 2014-15 season, Kessel signed an eight-year extension worth $64 million. When the Leafs traded him, his annual cap hit was eating $8 million of the team’s cap. They were anxious to get that substantial AAV off their books.
The Penguins gave up Kasperi Kapanen, Scott Harrington, Nick Spaling, a 2016 conditional first-round pick and a 2016 third-round pick to get Phil Kessel, Tim Erixon, Tyler Biggs, and a 2016 conditional second-round pick.
The jewel among the three players the Leafs received is Kapanen. He has been phenomenal for Toronto and has even spent time on the team’s top line. Getting a young, highly-skilled winger to develop with the Leafs made the trade retrospectively even better.
The Penguins were happy with what Kessel brought to their team. He played four years in Pittsburgh and even had a career-best 92-point season. More importantly, he helped the team win back-to-back Stanley Cups in 2016 and 2017.
The Leafs took advantage of the cap space they opened up and used it to help put together the team that they have now. Moving Kessel was the linchpin to the current construction of the team and the most important trade the Leafs made this decade.
It allowed them to finish last and draft Auston Matthews, and they turned one of the picks into Freddie Andersen.
We hope that all the moves that took place over the decade lead to bigger and better things in this next decade to come. Most importantly, hopefully, the 20s include a parade down Yonge St with the Stanley Cup.