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Boston Bruins Flashback: Trade that cost team multiple Stanley Cups

Michael DeVito
Michael DeVito

Chowder and Champions

1974; Goalie Ken Dryden #29 of the Montreal Canadiens defends the net during an NHL game circa 1974. (Photo by Melchior DiGiacomo/Getty Images)

Boston Bruins
A view outside of TD Garden, the venue that hosts the Boston Bruins (Photo by Maddie Meyer/Getty Images)

A few great, good, bad and several truly terrible trades in Boston sports history. The Boston Bruins might have made the worst.

Teams trade all the time. There are small trades, big trades and some trades that may appear minor at the time but have monumental consequences for the teams involved. We all seem to love trades. Some work out. Some don’t. Some turn out great, and some are disastrous. The ultimate gist of this story is one that was the latter for the Boston Bruins. A colossal disaster.

First, some other trades. One all-time great Boston trade was the trade of two rather inconsequential minor league pitchers to the Montreal Expos for a certain pitcher named Pedro Martinez. That one was an all-time great trade by Dan Duquette.

Then there was the all-time terrible trade (sale actually but that’s a trade for cash isn’t it?) of a certain slugger named Babe who was shipped out of Boston by then-owner Harry Frazee. That was an all-time, all-time bad trade. Maybe THE all-time bad trade, actually.

Yet, there have been other monumentally good Boston trades as well. The trade for the rights to the all-time best winning basketball player ever, the incomparable Bill Russell was a Celtics masterpiece by the great Red Auerbach The trade for Robert Parrish and Kevin McHale by Auerbach, two Hall of Fame players was another masterpiece.

And there have been several other memorable trades by Boston teams both good and bad that have punctuated Boston Sports history. Fans for some reason love trades. Maybe it’s the mystery. Maybe it the gamble of outfoxing the other side (they hope). Maybe it’s just fun to get in new faces who may just take your team to another level. We just love trades.

Boston Bruins
Bobby Orr  Boston Bruins (Photo by Bruce Bennett Studios via Getty Images Studios/Getty Images)

And then there are some major Boston Bruins trades to consider

Probably the greatest Bruins’ trade ever happened in 1967. This trade helped set the stage for two Stanley Cup victories. This was the trade in 1967 of Jack Norris, Pit Martin and Gilles Marotte to the Chicago Blackhawks for a certain Phil Esposito, Ken Hodge Sr. and Fred Stanfield.

Esposito was an All-Time great. Hodge was a goal-scoring wing and Stanfield was a really good second line center. All were excellent components of a run of great Bruins’ teams in the 1970s, the greatest run in the team’s history.

This was less a trade than “grand theft hockey”. The three Bruins along with a player named Bobby Orr helped lead the Bruins to two Stanley Cup victories. This was one of the all-time greatest trades in hockey if not sports history. Advantage Boston.

Conversely, a terrible trade was the trade of former first-round overall pick Joe Thornton for a bunch of no-names: Marco Sturm, Brad Stuart, and Wayne Primeau.

OUCH! Thornton, of course, has gone on to play for a total of 23 seasons, 15+ with the San Jose Sharks. Thornton has over 1500 points in his long career. Meanwhile, the players the Bruins received in return amounted to not very much. Not a good trade. Not good at all.

Boston Bruins
Ken Dryden (Photo by Richard Wolowicz/Getty Images)

But, THIS is the one Boston Bruins trade no one knows about that cost them several if not many sips from the Cup

Yet, there was one really, really, really bad Boston Bruins trade that makes the Thornton trade look like a win in comparison. Yikes, you say! How’s that?

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The one I have in mind is one few Boston Bruins fans have ever heard about. The fact that no one knows about and few remember this travesty is maybe a good thing. It’s really painful to even tell the story, and I doubt the Bruins have ever even mentioned this move publicly.

But the truth must be told! This trade is the polar opposite of the Esposito trade, but with even greater negative ramifications for the Bruins than the Esposito’s positive trade occasioned. Forgive me if I try to hold back a tear.

As you might guess, this trade happened quite a while ago and it happened during the greatest period in recent Bruins history. The Bobby Orr era.

This all-time cataclysmic trade occasioned a truly terrible cost to the great teams of this era led by the greatest Bruins and arguably the greatest NHL player (to have seen him was to believe it) ever, Bobby Orr. The terrible cost Boston paid, the loss of multiple Stanley Cups.

Yes, the name of the player who represents the worst trade in Boston Bruins history and perhaps in NHL history is Ken Dryden, goaltender, traded from the Bruins to the Montreal Canadians.

For younger readers who may not know of or even heard much if anything about Dryden and certainly can’t remember him, I can sum it up this way. In my opinion as a former goaltender myself, Ken Dryden was the greatest goaltender who ever played the game. Period.

I know there were the Patrick Roy’s, the Martin Brodeur’s and further back the Jacques Plante’s and others. But the king of the hill in my view was Ken Dryden.

Boston Bruins
Goalie Ken Dryden #29 (Photo by Melchior DiGiacomo/Getty Images)

Ken Dryden, a short career, but the greatest

Dryden won the Stanley Cup six times in only seven-plus seasons That’s the picture. An awful one for the Boston Bruins and especially their older fans, many of whom “haven’t the faintest” that Ken Dryden was once a Bruin.

This trade amounted to the worst trade in Bruins’ history, the worst trade probably in NHL history and clearly one of the worst trades in sports history, as well.

To close, and this is pure speculation, if that trade was not made, the Boston Bruins of the early 1970s would likely have created one of, if not THE greatest hockey dynasty in NHL history, to rival or even exceed the exploits of the Great Gretsky’s Edmonton teams. Bobby Orr, Phil Esposito, and Ken Dryden, on the same team?

Oh … what might have been. The Boston Bruins could have even more Stanley Cup banners hanging from the TD Garden rafters. The B’s would have been the New England Patriots of the NFL.

Michael DeVito

Michael DeVito

Michael is a long-time New England Patriots fan. He closely follows the Patriots' offseason team-building activities, including the Patriots' Draft, Free Agency, and Undrafted Free Agency. Michael also follows all Boston sports. He is also a big fan of the Chelsea Football Club in the English Premier League.