- 2010 1st Round Pick (2nd overall - Tyler Seguin)
- 2010 2nd Round Pick (32nd overall - Jared Knight)
- 2011 1st Round Pick (9th overall - Dougie Hamilton)
Toronto Receives: Phil Kessel
Date: September 18, 2009
In the fall of 2009, Peter Chiarelli made the trade that will likely define his career. He dealt Phil Kessel, the team's leading goal-scorer from the previous season, to division rival Toronto for three draft picks.
The following spring, the Bruins drafted Tyler Seguin second overall, and they picked up Jared Knight one round later.
Seguin was projected to become a franchise center, and although he has mostly played on the wing in Boston, he is quickly making good on his potential.
Although coach Claude Julien deployed the 18-year-old rookie cautiously in 2010-11, Seguin managed to contribute a handful of key goals in the playoffs. A four-point outburst in Game 2 of the Eastern Conference Finals against Tampa Bay foreshadowed a bright future.
Last season, Seguin was handed an expanded role, and he responded by leading the team in both goals (29) and points (67). He also finished second in the league in plus/minus with a plus-34 rating, trailing only his linemate Patrice Bergeron. If Seguin's development stays on track, he is set to become a franchise player in the very near future.
Jared Knight was selected 30 picks after Seguin and has yet to debut in Boston. After four superb seasons with the Ontario Hockey League's London Knights, the hard-working winger has joined the Providence Bruins for 2012-13. Knight has plenty of upside and his debut in Boston does not seem far away.
The third draft pick became Dougie Hamilton, who was taken ninth overall in 2011. The big offensive defenseman has dominated for the OHL's Niagara Ice Dogs over the past few seasons. Last year, Hamilton compiled 72 points in just 50 games, which earned him the Max Kaminsky Trophy as the OHL's best defenseman.
If not for the lockout, Hamilton would likely be playing in Boston right now. He is a favorite for the Calder Trophy, whenever his rookie season begins, and he projects to be an elite first-pairing defenseman down the road.
For Toronto, Phil Kessel has developed surprisingly well. Last season he finished sixth in the league in both goals and points. Kessel is a star in every way, but Toronto paid far too much for the American winger.
The Bruins may have lost one of their best players, but in return they received three potential stars who should carry the team for the next decade or two.
The deal has allowed the Bruins to position themselves for a decade of success in the wake of their 2011 championship. This trade is a superb example of Peter Chiarelli's ability to not only build a winning team but to maintain one.