Looking back at the Boston sports deadline deals that scored (and some that missed)

The acquisition of Taylor Hall is shaping up to be one of the best deadline pickups in Bruins history, if not Boston sports lore.

Taylor Hall
Taylor Hall has fit in nicely with the Bruins since being acquired at the trade deadline. Bruce Bennett/Getty Images

The Bruins coveted Taylor Hall – and as he’s since revealed, Taylor Hall coveted the Bruins – in the 2010 NHL Draft.

Owning the No. 2 overall pick, the Bruins were a spot too low to have a shot at getting the no-doubt No. 1 overall choice, ending up instead with decent consolation prize Tyler Seguin.

More than a decade later, Hall and the Bruins were finally united at the NHL trade deadline last month. He has fit in like he’s been wearing the Spoked B alongside Krejci, Brad Marchand, and Patrice Bergeron all along.

Hall has eight goals and six assists in 14 games with the Bruins, including an absolute beauty of a winning score in overtime against the Islanders Monday night. He’s reinvigorated two-time postseason scoring leader David Krejci, who hasn’t played with a winger blessed with anything close to his skill since Nathan Horton.


And I’d say he’s rather reinvigorated himself: Hall has already scored four times as many goals with the Bruins than he had in 37 games with the due-to-be-relegated-to-the-AHL Sabres this year.

He’s already shaping up to be one of the best deadline pickups in Bruins history, if not Boston sports lore.

If you think about it for even a moment, plenty of memorable deadline deals rush to mind. Across the major sports, there have been extraordinary in-season acquisitions and some regrettable ones too. They’ve tended to fall into three categories:

  • Bold moves for the moment, or trading for established stars to aid an immediate championship quest.
  • Smaller deals that enhance the quality depth of a contending roster (a Bill Belichick specialty).
  • Dealing veterans for young players that ideally help out down the road (early indications are that this could be a Chaim Bloom specialty).

The Hall deal, which also brought Curtis Lazar to Boston while general manager Don Sweeney sent forward Anders Bjork and a second-round pick in return, fits that first category. The closest trade to it in Bruins history is probably the 1992 swap with the Blues that brought Adam Oates aboard while sending Craig Janney and Stephane Quintal to St. Louis. Oates proved the ideal setup man for Cam Neely – kind of the inverse of what Hall is for Krejci – while tallying 499 points in 368 games in Boston, including a 45-goal, 97-assist season in 1992-93.

Since the Oates deal happened in February, several weeks before the deadline, we’ll have to put an asterisk on it here.


Because they almost always have had some level of championship aspirations over the last decade-plus, the Bruins have made several meaningful moves at the actual deadline, including acquiring a couple of Mario Lemieux-era former Penguins superstars in Mark Recchi (2009) and Jaromir Jagr (’13).

Recchi proved crucial on the ice and in the locker room during the Bruins’ ’11 Cup run. Jagr didn’t work out quite so well, going goalless in the ’13 postseason, but he was a blast to have around. It was mesmerizing during his snakebitten performance that postseason to watch him go out, solo, on the Garden ice after a game and put himself through a grueling workout. No wonder he lasted in the league until age 45, five seasons beyond his frustrating Bruins stint.

The biggest Bruins deadline trade actually sent away a franchise icon so he could pursue a Stanley Cup elsewhere. Fans get grief for celebrating Raymond Bourque’s championship with the Colorado Avalanche at City Hall in 2001, but the real embarrassment is that the Bruins put themselves in such a hopeless spot that such a classy player had to unite with Patrick Roy to win.

Sometimes, trading a star ends up igniting the team he left behind. Jason Bay had one-and-half excellent seasons here after the Red Sox got him in a three-team transaction that ended the Manny Ramirez era in 2008, and manager Terry Francona ranked his team that year as perhaps the best he ever had.


I think we can all agree that Nomar Garciaparra was superior to Derek Jeter from 1997-2003. [Everyone that has somehow managed to read this far nods in agreement.] But Red Sox history would be much different, and 2004 would not have been nearly as cathartic or satisfying, had Theo Epstein chickened out on trading him that July to the Cubs in a three-way trade that brought steady Orlando Cabrera and Doug Mientkiewicz to the Red Sox.

The afterthought deal that same day worked out pretty well, too: I don’t know much about Henri Stanley, sent to the Dodgers that day, but I’ll never forget a thing about Dave Roberts.

There have been many fulfilling deadline deals for quality if unheralded players that went on to have memorable runs here.

Dennis Seidenberg, acquired from Florida in 2010, was a rock-steady defensive partner alongside Zdeno Chara on the Cup champs.

Isaiah Thomas, picked up by the Celtics from the Suns in February 2016, had a truly magical run, and nothing with the franchise has gone quite right since his career-altering hip injury in May 2017.

Belichick’s deadline deals for Aqib Talib (2012) and Kyle Van Noy (2016) brought the Patriots a couple of defensive cornerstones at minimal cost.

Sweet-swinging switch-hitter Victor Martinez (2009) put up an .865 OPS over a season-and-a-half after coming to the Red Sox from the Indians. You kind of forgot about him, didn’t you?

The worst and best deadline deals in Boston sports annals involve prospects and the Red Sox. Jeff Bagwell for Larry Andersen in 1990 haunts here. Jason Varitek and Derek Lowe for Healthcliff Slocumb in 1997 haunts in Seattle.


The 1988 trade that delivered prospects Curt Schilling and Brady Anderson to Baltimore for reliable veteran Mike Boddicker worked the way those kinds of deals are designed to. Schilling and Anderson developed into stars, though it didn’t happen for Schilling until he was with his fourth organization. Boddicker was a dependable cog in the rotation on the Red Sox’ 1988 and ’90 AL East champs.

Giving up a good prospect who ultimately pans out – like the Bruins did in Blake Wheeler in 2011, along with Mark Stuart, to get Rich Peverley – is worth it if the deal aided a fulfilled championship pursuit.

Sometimes there are unsentimental deals that send a favorite away, leaving the home fans cold. Few liked Danny Ainge’s NBA deadline trade of Kendrick Perkins to Oklahoma City in 2011, though it was probably the right thing to do. And few liked it when Ainge himself was traded back in 1989, to the Kings for taller folks Ed Pinckney and Joe Kleine.

Hall is still in the early stages of etching a place in Boston sports and Bruins history. Who knows if it will even last beyond this spring given his pending free agency. But right now, he’s playing like a Bruins lifer – and with each goal, rising up the list of deadline deals to appreciate.

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