Phil Kessel is a three-time Stanley Cup champion and is still unsigned as a free agent for the upcoming season. Recently, Kessel announced that he was willing to break his Ironman streak in order to continue his career in the NHL.
Kessel's decision to potentially end his Ironman streak will go a long way in negotiations, as no team wants to be put in a difficult position to end it. With the OK from Kessel, this opens him up as a valuable depth scorer who also is a well-known locker room guy and has extensive playoff experience.
Toronto could use all of those things on their roster. If the money is right, which, since he is still unsigned with a desire to play it might be, Toronto and Kessel could have a reunion in the future. There is clearly a new era being ushered in for the Leafs, and that might further draw Kessel back to his longest-tenured team.