Vote: Is Phil Kessel for Tyler Seguin and Dougie Hamilton the Best Trade in Boston Sports History?

Tyler SeguinAny time the Bruins travel to Toronto, Peter Chiarelli must have a tiny smirk on his face.

In September of 2009, the Bruins general manager sent forward Phil Kessel (and his six-million dollar contract) to the Leafs for their first-round picks in 2010 and 2011, with a second-round pick tossed in for good measure.

The next year, Boston drafted former Plymouth Whalers forward Tyler Seguin with the second overall pick in the draft. In two-plus seasons in Boston, Seguin has 71 points and is a plus-35 overall.

With the second of the inherited Toronto first-rounders, the Bruins took defenseman Dougie Hamilton in the 2011 draft. Hamilton is already a full-time Bruin and has four points in his first seven games in Boston. Meanwhile, in three seasons with the Maple Leafs, Kessel has matched his highest goal total in Boston only once. His 37 goals last season was the highest total of his career, but the 25-year-old forward is a minus-40 since arriving in Toronto.

However, the Bruins are not the only team to pull off a lopsided trade in the history of Boston sports. At the 1997 MLB trade deadline, then-Red Sox general manager Dan Duquette sent closer Heathcliff Slocumb and his 5.79 ERA to the Seattle Mariners. In return, Boston received catcher Jason Varitek and pitcher Derek Lowe.

Slocumb would only record 19 more career saves in three seasons. Meanwhile, Varitek would go on to catch over 1,500 games and help the Red Sox win World Series titles in 2004 and 2007. In 2005, the Red Sox named Varitek their captain, a title that remained until his retirement in 2012.

Lowe would pitch seven seasons in Boston, and threw his first career no-hitter against Tampa Bay in 2002. In 2004, he became the first pitcher to record a win in all three of his team’s series-clinching games when Boston won its first World Series in 86 years.

In 2007, the Patriots conducted a brilliant trade of their own. During the 2007 NFL draft, Scott Pioli sent the Patriots’ fourth-round pick (110th overall) to Oakland. In return, the Patriots acquired future Hall of Fame wide receiver Randy Moss. In 2007, Moss caught an NFL-record 23 touchdown passes and had 1,493 receiving yards. Moss’ efforts helped lead New England to a 16-0 regular season and appearance in Super Bowl XLII.

For what it’s worth, the player Oakland took with the 110th pick overall, cornerback John Bowie, is currently a practice squad member for the Cincinnati Bengals and has two career NFL tackles.

Back in 1980, Red Auerbach also pulled off a brilliant deal which led the Celtics to multiple championships in the 80s. The Celtics possessed the first and 13th overall picks in the 1980 draft. Auerbach traded them to Golden State for the third overall pick and Robert Parish. Boston would select Kevin McHale with the third pick. Parish would go onto score over 20,000 points and record 3,000 blocks during his Boston tenure.

McHale spent his entire career with the Celtics and scored over 17,000 points. McHale led the league in shooting percentage twice in his career and also helped Boston win three titles.

Which gets your vote as the best trade in Boston history?

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