7 Biggest Trades in Boston Bruins History, Ranked

The Boston Bruins are one of the most storied franchises in the National Hockey League. An Original Six team, Bruins fans have seen ups, downs, and everything in between.

They’ve also witnessed some of the most lopsided trades in the history of the NHL.

From Cam Neely to Joe Thornton to Adam Oates, check out the seven biggest trades in Bruins’ history.

7 Biggest Boston Bruins Trades in Team History

1. Pit Martin, Jack Norris, and Gilles Marotte for Phil Esposito, Ken Hodge, and Fred Stanfield

Everything changed for the Bruins with this trade.

The Bruins had missed the playoffs for eight years on the spin before the 1967-1968 season. Looking to shake things up, general manager Milt Schmidt acquired Phil Esposito from the Chicago Blackhawks.

Schmidt’s plan worked.

Boston made the playoffs 29 seasons in a row after the trade, and Esposito played an integral role in the club capturing a pair of Stanley Cups in 1970 and 1972.

Esposito won the Art Ross five times during his tenure with the Bruins, and his 76-goal campaign in 1970-1971 is tied with Alexander Mogilny for the fifth-most in a single campaign.

2. Barry Pederson for Cam Neely and a First-Round Pick  

This is widely considered one of the most lopsided trades in NHL history, but at the time it seemed like a fair swap. At least, that’s what fans of the Vancouver Canucks will want to think.

Barry Pederson had two 100-point seasons before he turned 24 with the Bruins, but they sold high and were able to land Cam Neely, a promising power forward, in the swap.

It turned out to be a massive coup for the Bruins.

Neely quickly became a fan favourite in Beantown and hit the 50-goal mark three times, including completing the feat in 49 games in 1993-1994. 

Neely’s number was retired by the Bruins in 2004 and he has served as the team president since 2010.

3. Joe Thornton for Marco Sturm, Wayne Primeau, and Brad Stuart

If the trade for Neely was a coup for the Bruins, this deal was the opposite.

Joe Thornton was seen as a franchise cornerstone from the moment the Bruins drafted him first overall in the 1997 NHL Draft. The hulking centre blended size and skill, and he averaged a point-per-game in the four seasons leading up to the 2004-2005 lockout.

But the Bruins’ brass felt like they needed to send a jolt into the locker room because the team was getting complacent. That led to the rash decision to trade Thornton to the San Jose Sharks in the middle of the 2005-2006 season.

It would go down as one of the worst NHL trades in league history – and it didn’t take long to age poorly.

Thornton won the Hart Trophy in the season he was traded and would become an all-time great for the Sharks, who were often listed among the NHL betting favourites during Thornton’s tenure.

4. Ron Grahame for a First-Round Pick (Raymond Bourque)

This one didn’t get much fanfare when it was made official, but it would end up being one of the most important moves in the Bruins’ history.

The Los Angeles Kings were looking to upgrade their goaltending before the 1978-1979 season, and they sent a first-round pick to Boston for Ron Grahame with that goal in mind.

Fortunately for Boston, Raymond Bourque would still be available when they selected ninth overall.

Bourque played 21 seasons with the Bruins and holds the franchise record for games played and points.

5. Andrew Raycroft for Tuukka Rask

Score this one for the Bruins.

Andrew Raycroft’s career got off to a promising start when he won the Calder Trophy in 2003-2004, but his numbers declined quickly after that season and the B’s were worried the goaltender would be a one-hit wonder.

Knowing they had a decent starting goaltender in Tim Thomas, the Bruins felt comfortable trading Raycroft to the Toronto Maple Leafs for Tuukka Rask, a blue chip goaltending prospect.

Raycroft’s career would stall out with the Leafs, while Rask would completely rewrite the goaltending record books with the Bruins.

Rask’s Bruins would spend a good chunk of the 2010s as a Stanley Cup favourite, according to hockey betting lines. 

6. Craig Janney and Stephane Quintal for Adam Oates

This was another steal for the Bruins.

Adam Oates was in a bitter contract dispute with the St. Louis Blues before the 1991-1992 season. After putting up back-to-back 100-point campaigns, Oates felt he deserved a raise.

It never came, and the relationship turned tumultuous and ended up with a trade to the Boston Bruins.

Oates would play a starring role in Boston, putting up 499 points in 368 games.

7. Ken Dryden and Alex Campbell for Guy Allen and Paul Reid

This is a double whammy.

Not only did it mean that the Bruins would lose out on Ken Dryden being their goaltender, but they sent him to their bitter rivals, the Montreal Canadiens, where he would win six Stanley Cups and five Vezina Trophies.

It was a nondescript trade at the time it was made, but it would have massive ramifications.