Both the 2005 and 2006 seasons represented a changing of the tides for the Boston Bruins.
Over the span of those two years, Mike O’Connell, Jeff Gorton and Peter Chiarelli orchestrated a number of moves that uprooted the Original Six franchise — dealing away Joe Thornton, adding Zdeno Chara and investing in the future with youngsters like Patrice Bergeron.
Given the amount of upheaval felt in those two years, we figured we’d take a long look at all the moves taken in the post-lockout era that have allowed Boston to keep a Cup-contending window open for over a decade now.
After sorting through over 40 free-agent signings from 2005 onwards, we decided to take a look at all the trades struck by O’Connell, Gorton, Chiarelli and Don Sweeney.
In total, there were over 90 trades struck between the Bruins and other clubs since the 2004-05 lockout, although we’ve whittled this list down to 71 — with AHL-centered transactions not making the cut.
The Bruins have run the full gamut when it comes to placing your odds on the trade market, with the Original Six franchise emerging with some steals — and a number of duds — over the past 15 years.
Without further ado, let’s get started with the five worst B's deals since 2005:
71: So long, Jumbo - Nov. 30, 2005
To Boston:
Marco Sturm
Brad Stuart
Wayne Primeau
To San Jose:
Joe Thornton
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Ah, yes — the franchise-altering deal that ruined my childhood and left many Bruins fans scratching their heads.
Now, let’s be clear — O’Connell’s decision to ship Boston’s 26-year-old franchise star out to the West Coast did have some reasoning behind it. By dealing Thornton, Boston freed up cap space necessary to ink both Zdeno Chara and Marc Savard to new contracts the next summer, prompting a reset and change in leadership that eventually led to Boston hoisting the Stanley Cup a little over five seasons later.
Add in the development of youngsters like Patrice Bergeron and David Krejci, and Boston’s pipeline of talent down the middle, especially with Savard added to the fold in 2006, allowed Boston to absorb some of the hit that came with Thornton’s departure.
Still, as is always the argument when it comes to assessing this blockbuster, the Bruins could (and should) have received more, right?
While Sturm had a few productive seasons in Boston (and scored some key goals in the playoffs), Stuart was a solid blueliner and Primeau added depth, that trio failed to come close to the production Jumbo Joe put forward in San Jose — with the star center winning the Hart Trophy in 2005-06 after accumulating 92 points (20 goals, 72 assists) over 58 games. Thornton, now 41, is still kicking in San Jose, with the future Hall of Famer racking up 1,055 points over 1,104 games out in California.
Yes, Boston did manage to win a Cup before San Jose, so perhaps starting off this list might be viewed as overkill.
But considering that Brian Burke, then GM of the Ducks at the time of the Thornton deal, said earlier this year that Anaheim put forward a whammy of an offer for the B’s star — it does make this trade an even tougher pill to swallow.
I don’t know about you, but I’d take one of Ryan Getzlaf or Corey Perry over anything O’Connell managed to net in dealing away a Hall of Famer.
Sigh.
70: Shipping off Seguin - July 4, 2013
To Boston:
Loui Eriksson
Reilly Smith
Matt Fraser
Joe Morrow
To Dallas:
Tyler Seguin
Rich Peverley
Ryan Button
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Did Seguin’s immaturity and ugly showing during the 2013 Stanley Cup Playoffs pave the way for such a trade? Yes, of course.
In fact, Boston had a right to be awfully steamed, given that — had Seguin managed to chip in with more than just one goal and eight points over 22 playoff games that summer — the Bruins very well could have won their second Cup in three years.
Still, for all those frustrations, opting to deal away a 21-year-old budding star (and a pretty agreeable six-year, $34.5-million contract signed less than a year prior) looked like a foolhardy move from the jump — and this trade has continued to sour with age.
When healthy, Eriksson had a productive three-year stretch with Boston (147 points in 224 games), but he headed west to Vancouver on a six-year, $36-million deal at the end of the 2015-16 season. Smith had a very productive first year in Boston and was foolishly traded to Florida in 2015 (more on that in a bit), while both Morrow and Fraser failed to establish themselves as regular NHLers.
Meanwhile, since the trade, the 28-year-old Seguin has now tallied 223 goals and 514 total points over 538 games with the Stars.
Again, Boston managed to win a Presidents' Trophy the year after Seguin’s departure and have once again re-opened a Cup contention window for at least a few more seasons, so the Bruins haven’t faced truly dire ramifications from such a move.
Still, having an offensive dynamo like Seguin could have helped the Bruins juuuuuust a tad over the last couple of seasons.
69. Dougie dips - June 26, 2015
To Boston:
2015 1st-round pick (Zach Senyshyn)
2015 2nd-round pick (Jakob Forsbacka Karlsson)
2015 2nd-round pick (Jeremy Lauzon)
To Calgary:
Dougie Hamilton
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Now, to be fair, Boston’s hands were pretty tied in June 2015. Already dealing with cap constraints, it became rather evident that a scenario in which Hamilton re-upped in Boston was not going to pan out, as the young defenseman’s camp wasn’t entertaining any offers that the Bruins were tossing out for the RFA.
As such, Boston opted to part ways with the 22-year-old blueliner, gaining three picks in what was a loaded 2015 NHL Draft. Now, stop if you’ve heard this before, but Boston didn’t exactly hit a home run over those two days in Florida, especially during a first round in which the B’s passed on the likes of … Mathew Barzal, Kyle Connor, Thomas Chabot, Brock Boeser and Travis Konecny.
Calgary’s first-round pick was used by Boston to scoop up Zach Senyshyn — a winger already considered a reach that has yet to crack a regular spot up in the NHL ranks. In the second round, Boston did use one of the Flames’ selections to take Jeremy Lauzon (one of the few saving graces in this deal), while the other second-round selection was used on Jakob Forsbacka Karlsson — who opted to put his NHL career on pause and return to play in Sweden last year.
Given how evident it was that Hamilton did not want to be in Boston, Sweeney and his staff were between a rock and hard place with this move, but the return here was still extremely underwhelming. All it’d take is just one of Barzal, Connor or another impact forward to shoot this deal way up the rankings.
68: Versteeg breaks through - Feb. 3, 2007
To Boston:
Brandon Bochenski
To Chicago:
Kris Versteeg
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For a brief moment, this trade looked as though it was panning out — as Bochenski tallied 22 points over 31 games in his first season in Boston, while Versteeg was still toiling away down in the AHL.
But it didn’t take long for Versteeg, Boston’s fifth-round pick in the 2004 NHL Draft, to flip this deal in favor of Chicago. In his first two full seasons up in the NHL, Versteeg tallied 42 goals and 97 points over 157 games — while helping Chicago win its first Stanley Cup since 1961 by racking up 14 points over 22 playoff games in 2010.
While Versteeg eventually retired with 358 points over 643 career games, Bochenski ultimately only played in 51 total games with Boston before being dealt to Anaheim on January 2, 2008.
67. No hometown discount - July 1, 2015
To Boston:
Jimmy Hayes
To Florida:
Reilly Smith
Marc Savard
At the time, this deal seemed like a pretty solid swap for Boston.
Along with freeing up some money by dealing Savard’s contract (allowing Boston to throw cash at … Matt Beleskey!), Boston dealt what was a talented, but inconsistent, Smith to the Panthers in exchange for Dorchester product Jimmy Hayes.
What’s not to like? Well, things went off the rails rather quickly after Hayes signed a three-year, $6.9-million contract with Boston.
After tallying 29 points in 75 games with Boston in his debut campaign in 2015-16, Hayes spent about half of his second season in Boston as a healthy scratch — only tallying two goals and five total points over 58 games. The BC product was bought out before his final season in Boston, with Hayes failing to log a game in the NHL since 2018.
Meanwhile, even if Boston wasn’t crazy about Smith’s higher cap hit and up-and-down play, the winger has been a middle-six staple with both the Panthers and Golden Knights since that deal. In the past five seasons, Smith has eclipsed 50 point-threshold in four campaigns — along with 27 goals through 71 games with the Golden Knights this year.
Next up, No. 66-61 — featuring a couple other misfires during both the Chiarelli and Sweeney eras.

(Photo by Don Smith/NHLI via Getty Images)
Bruins
Ranking Bruins’ post-lockout trades: Franchise stars sent packing highlight bottom of barrel (No. 71-67)
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