Phil Kessel
This one still hurts for a lot of Boston Bruins fans. One can’t help but wonder how differently things could have turned out had the Bruins held onto Phil Kessel, who became a prolific goal-scorer for the Toronto Maple Leafs and Pittsburgh Penguins.
Kessel was the 5th overall draft pick in 2006, and in three seasons with the Boston Bruins amassed 126 points in 222 games. He became the first rookie in NHL history to win the Bill Masterton Memorial Trophy after he underwent surgery for testicular cancer and returned to the Bruins lineup in short order, missing only 11 regular season games.
He was traded in 2009 to the Maple Leafs for draft picks which eventually became Tyler Seguin, Dougie Hamilton and Jared Knight.
Hindsight is a funny thing.
During his tenure in Toronto, Kessel racked up four 30-goal seasons and was nominated to the All-Star Game three times. After toil and trouble erupted in Toronto, trade rumors about Kessel swirled and he was the subject of a bizarre Toronto Sun article that chronicled his reported affection for hot dogs.
Kessel had the last laugh, helping Pittsburgh win two straight Stanley Cups in 2016 and 2017. After four seasons with the Penguins he was traded to the Arizona Coyotes for Alex Galchenyuk and Pierre-Olivier Joseph.
All this trade drama makes it hard to remember that just ten years ago he was skating in the Black and Gold. It’s unclear how Kessel’s third fresh start will fare for him, but if Arizona doesn’t cut it for him, I hear Boston has good hot dog stands.
All roads lead to the Hub, Phil!