On September 18, 2009, this historic trade between the two rival teams took place which would forever shape the future of both franchises.
The trade sent Phil Kessel to the Maple Leafs - in exchange for a 2010 first-round pick, a 2010 second-round pick, and a 2011 first-round pick.
2010 1st: The Bruins selected Tyler Seguin.
2010 2nd: The Bruins selected Jared Knight.
2011 1st: The Bruins selected Dougie Hamilton.
This was a pretty solid haul for the Bruins in exchange for Phil Kessel.
However, if the Leaf's had not made this trade, they would have had a franchise player in Tyler Seguin and a top-2 defenseman in Dougie Hamilton.
How it ended up
Seguin would only spend three seasons with the Bruins, before being traded to the Dallas Stars in a package for Loui Eriksson, Reilly Smith and multiple prospects.
Hamilton also spent three years with the Bruins before being sent to the Calgary Flames for multiple draft picks.
Kessel had four good years with the Toronto Maple Leafs, before being sent to the Pittsburgh Penguins in 2015.
14 years later, there is not a single player remaining on the Bruins roster who was apart of the initial Phil Kessel trade.
Who won the Kessel-Seguin trade?
Boston Bruins
Toronto Maple Leafs
Neither
