#2. What if the Leafs never traded for Phil Kessel?
In 2009, Brian Burke traded two first round picks and a second round pick for Kessel. At the time, the move seemed justified as the opportunity to bring in a prolific goal scorer was something the Leafs desperately needed.
However, two of those draft picks turned into Tyler Seguin and Dougie Hamilton, and although Kessel had four 30-goal seasons in Toronto, the team never had playoff success and Kessel was a punching bag for Toronto media.
So what would have happened if Kessel never became a Leaf?
While, the team would have had two first round draft picks that could have shaped the franchise. It’s possible that the Tyler Seguin experiment would have been too much in Toronto. Seguin was known for his party lifestyle and getting drafted to his hometown team could have been too much to handle for the young player.
The Bruins saw Seguin’s off-ice routines as an issue and traded him only three years into his career, despite his numbers being great.
And although Boston drafted a good defenseman in Dougie Hamilton, if the Leafs kept that pick, it’s possible they would have screwed it up. For example, in that same draft the Leafs drafted Tyler Biggs and Stuart Percy when players like Boone Jenner and Rickard Rakell were available.
So although the Leafs traded away a lot of assets for a one-trick pony in Kessel, it’s likely management wouldn’t have drafted well with the picks they had, so at least fans had the pleasure of watching Kessel for a few years.