Originally written on NESN.com  |  Last updated 11/16/14
Any time the Bruins travel to Toronto, Peter Chiarelli must have a tiny smirk on his face. In September of 2009 Chiarelli, 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 Doguie 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 best 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 would receive 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 in 2002 he threw his first career no-hitter against Tampa Bay. In 2004, he became the first pitcher to record a win in all three of his team’s clinching games when Boston won its first World Series in 86 years. In 2007, the Patriots would conduct 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 multiples 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. Take Our Poll

Miller to Oregon transfer rumor originates on Reddit

Valencia FC ditches bat logo amidst DC Comics challenge

Paul Pierce: Celtics' Big Three was like 'Holy Trinity'

Cubs reportedly offer Jon Lester more than $135 million

Colin Kaepernick: Jim Harbaugh will be back in 2015

Jeremy Maclin not happy with Riley Cooper’s contract remark


Broncos reportedly waive kicker McManus, sign Connor Barth

Report: Browns not committed to Brian Hoyer long-term

Pablo Sandoval, Red Sox officially agree to contract

Ex-NFLer passed out in Wendy's drive-thru, arrested for DUI

Ex-NFL DB Fred Smoot arrested on domestic assault charges

Jets’ Sheldon Richardson: ‘I didn’t get drafted to lose games’

Aaron Rodgers blasts those who accused him of trolling Vikings

The century's 10 most one-sided college football rivalries

WATCH: The Good, the Bad and the Ugly of NBA's first month

Sherman mocks NFL media policies in press conference

Why Packers' offense continues to evolve despite success

'Fire Idzik' billboard updated with suggestion for Jets owner

Watt buys pizza, shows gratitude to Houston firefighters, cops

College football's post-Week 13 Playoff projection

Which teams have the best shot at an undefeated season?

Infographic: Terrell Suggs' sack victims after notching 100th

Dude Perfect video features Russell Wilson, Pete Carroll

Rick Pitino 'played four white guys and an Egyptian' in blowout

NHL News
Delivered to your inbox
You'll also receive Yardbarker's daily Top 10, featuring the best sports stories from around the web. Customize your newsletter to get articles on your favorite sports and teams. And the best part? It's free!

By clicking "Sign Me Up", you have read and agreed to the Fox Sports Digital Privacy Policy and Terms of Use. You can opt out at any time. For more information, please see our Privacy Policy.

Braxton Miller headed to Oregon?

Century's most one-sided CFB rivalries

Pierce: C's Big Three like 'Holy Trinity'

Maclin unhappy with Cooper comments

Post-Week 13 CFB Playoff projection

What has Masai Ujiri built in Toronto?

How L.A. should replace Hanley

Lester, Red Sox still talking contract

Why each NFL team should be thankful

Could Kentucky beat the 76ers?

Greatest college football rivalries

LeBron on losing streak: 'I stink'

Today's Best Stuff
For Bloggers

Join the Yardbarker Network for more promotion, traffic, and money.

Company Info
What is Yardbarker?

Yardbarker is the largest network of sports blogs and pro athlete blogs on the web. This site is the hub of the Yardbarker Network, where our editors and algorithms curate the best sports content from our network and beyond.