Phil Kessel and Tyler Seguin battle for a loose puck.
I'd be remiss when talking about the Bruins and Leafs' shared history if I didn't mention the Phil Kessel trade.
In 2009, the Bruins traded Kessel to the Leafs for two first-round picks and a second-round pick, as part of Brian Burke's strategy to jump start a rebuilding in Toronto.
The Bruins used those two picks to select Tyler Seguin and Douglas Hamilton. Seguin provided some valuable speed and scoring as a rookie when the Bruins won the Stanley Cup in 2011.
The depth provided by Hamilton helped the Bruins feel secure enough in their prospect depth to trade picks back to Toronto to acquire Tomas Kaberle at the 2011 trade deadline. Kaberle, like Seguin, would provide some valuable depth and secondary scoring to help the Bruins hoist the Stanley Cup.
To add insult to injury, both Hamilton and Seguin are looking like future stars and are from the Greater Toronto Area to boot. They sure would have looked good in blue and white—instead, the Bruins get to rub salt into the wound by having the pair make big plays against the Maple Leafs for the foreseeable future.