The History of Trades Between the Toronto Maple Leafs and Boston Bruins
By Kyle Cushman
The Biggest Trade
Date: September 18, 2009
Leafs Acquire: Phil Kessel
Bruins Acquire: 2010 1st (Tyler Seguin), 2010 2nd (Jared Knight), 2011 1st (Dougie Hamilton)
It’s rare that you see a trade of this magnitude between in division rivals in the NHL, but just before the start of the 2009-10 season, Brian Burke pulled off a blockbuster.
Everyone here knows how this trade panned out, so let’s give more context as to what it was like when the deal first went down.
Phil Kessel was a restricted free agent and the Bruins were struggling to put a contract together. A deal in the range of a four year, $16-million contract was rejected by Kessel early on in the offseason. Whether Kessel requested a trade is debated, but it was clear Kessel and the team did not see eye to eye.
Even at the time, Burke recognized the extremely high price being paid. But given where the Toronto Maple Leafs expected to be with Kessel in the lineup, it was a price that made sense on the surface.
Kessel was coming off of a massive third year in the NHL. Playing 16:34 a night, his 36 goals were most on the Bruins and would have led Toronto by 11. Just four years removed from being selected fifth overall, the Leafs were banking on Kessel coming in and being the star player that takes them over the edge to becoming a playoff contender.
It was quite the gamble, to say the least. Toronto had just finished last in the Northeast Division with 81 points, 12 out of a playoff spot. Despite the significant ground to make up, Burke believed that the addition of Kessel would make them competitive right away. In fact, he said so almost verbatim the day of the trade.
That’s exactly where the Kessel trade fell flat on its face. The 2009-10 Toronto Maple Leafs were abysmal. Injuries, lacklustre play, and brutal goaltending all combined to make Toronto the second-worst team in the NHL.
If the Leafs were even moderately competitive the first two seasons with Phil Kessel, the trade is likely one of the best made in recent Leafs history. Kessel led the team in scoring every year he was in Toronto, but he rarely had any help. That was especially true in his first two years with the Leafs, the two most important ones as it would decide what value the Bruins would get out of the trade.
And that’s exactly why things just never worked in Toronto. Kessel not only had to carry the team on his back, but he also had to live up to the expectations of a player acquired for a second overall pick, a ninth overall pick, and a high second-round pick. It was too much to overcome and hurt his stance within the fanbase essentially from Day One.
Boston receiving Tyler Seguin and Dougie Hamilton out of the Kessel trade made this the worst-case scenario for Toronto. Not only did they lose the second overall pick and a future first-line centre in Seguin, but Boston also hit a home run on the ninth overall pick a year later and snagged one of the premier defencemen in the NHL today.
The only silver lining that Leafs fans can find in the price paid to get Kessel is that the Bruins failed to get much value for either Seguin or Hamilton. Boston got three high-end seasons from the pair before shipping them out for mediocre returns, a vast contrast to the return they got for Kessel.
It truly is unfortunate the circumstances under which Phil Kessel came to Toronto. If not for the price causing the fanbase agony for years following, Kessel is likely a much more beloved figure. It’s easy to forget that Kessel scored at a 30 goal pace each of his first five seasons with the Toronto Maple Leafs and didn’t miss a single game after making his debut.
In a normal situation, that makes a player loved in a city. For Kessel and Toronto, it could never just be “normal”.