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Eight Most Shocking Trades In Boston Sports History

UPDATE (June 16, 2025): Little did I know.

It’s been just four months since this post was sent out into the ether, but a ton has changed ever since the “publish” button was clicked. I was a young, brash, bright-eyed and bushy-tailed writer back then, but the last four months have turned me into a hard-nosed, grizzled veteran of the business.

(I wish this was more of a joke than it actually is.)

I thought this post would be a bit more evergreen than it ended up being, but that’s nothing that a late entry can’t fix! Can you guess where we’re headed?

Rafael Devers gets traded to the San Francisco Giants

Devers’ shipment from one coast to another wasn’t just surprising, but perhaps the biggest shock that any of us have felt since the infamous Nomar Garciaparra trade of 2004. The Red Sox soured on the face of their franchise over the course of a few rocky months, and elected to send him away rather than solve whatever issues had reached a boiling point.

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We saw the tension start to bubble, but did anyone think this was going to happen?

ORIGINAL STORY (Feb. 9, 2025): The Dallas Mavericks shocked the world on Saturday, making the still-unbelievable decision to trade superstar Luka Doncic to the Los Angeles Lakers.

It’s probably one of the most shocking trades in the history of sports, which got us thinking about the most shocking trades in the history of Boston sports.

Let’s discuss, shall we?

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Alex Rodriguez gets traded to the New York Yankees

Rodriguez is now one of the biggest villains in Boston’s long and illustrious sports history, but there was once a time when he seemed destined to become the city’s biggest star.

The Red Sox had a deal in place to acquire the superstar shortstop from the Texas Rangers back in 2004, but it eventually fell through due to the MLBPA’s refusal to accept an amendment to his contract. The Yankees then swooped in to get a deal done, being motivated to pull the trigger after third baseman Aaron Boone tore his knee up playing pickup basketball — a truly shocking outcome at the time.

Kevin Garnett and Ray Allen get traded to the Boston Celtics

Garnett and Allen were technically acquired in two separate trades, but one quite literally needed to happen before the other.

The Los Angeles Lakers and Phoenix Suns were initially at the forefront of the sweepstakes to acquire the former, who had to sign off on any potential deal away from the Minnesota Timberwolves. The Celtics weren’t viewed as a legitimate option but found themselves in contention after acquiring Ray Allen from the Seattle SuperSonics. KG then reevaluated things and signed off on a deal to make a new Big Three.

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Randy Moss gets traded to the New England Patriots

Moss was the best wide receiver in the NFL, but two disappointing seasons with the Oakland Raiders (and some off-field troubles) forced him down the list of desirable trade targets. The Patriots weren’t scared of a challenge, though, and traded a fourth-round pick for the wideout who would go on to have the greatest season in the history of the position.

Kevin Garnett and Paul Pierce get traded to the Brooklyn Nets

Garnett’s career in Boston both started and ended with shocking trades.

The Celtics were coming off three conference finals appearances in six seasons by the time 2013-14 came around, but it was evident that Garnett and Pierce’s best days were behind them. The Nets hadn’t been informed, however, and made the shocking decision to trade a bunch of scrubs and the rights to four first-round picks in return, which essentially accelerated the rebuild in Boston.

Jaylen Brown and Jayson Tatum turned out to be pretty decent.

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Josh Beckett, Adrián González and Carl Crawford get traded to the Los Angeles Dodgers

The Red Sox had to get out from underneath the albatross contracts they signed Beckett, González and Crawford to by the time 2012 rolled around, and they did it in a really creative way.

The Dodgers were willing to take on big money even back then, but seeing as the trade deadline already passed when this deal took place, all players had to be placed on waivers first. LA then threw together a decent enough package for Boston to fully take the plunge, and nearly a quarter billion dollars exchanged hands — all for the team that was resetting to win multiple championships within the next six years.

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Nomar Garciaparra gets traded to the Chicago Cubs

Garciaparra’s time in Boston took a nosedive at the end, with multiple controversies telling the story of his final season with the club. The Red Sox needed to move on, but doing so at the deadline in the middle of a wild card run was shocking.

We all know how it worked out in the end, though.

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Bill Russell (kinda) gets traded to the Boston Celtics

Russell was far and away the best prospect entering the 1956 NBA Draft, so things had to get a little zany for him to end up with the Boston Celtics.

Red Auerbach knew that, so he not only traded Ed Macauley, Cliff Hagan, and the No. 7 pick to the St. Louis Hawks for the No. 2 pick, but he had to make sure that the player would still be available. Auerbach ensured that he would by renting out “The Ice Capades” to the Rochester Royals so they’d pass up on the greatest winner in basketball history.

Yes, that’s a true story. It might not have been shocking at the time, but it certainly is looking back.

HONORABLE MENTIONBruins: Joe Thornton gets traded to the San Jose SharksPatriots: Lawyer Milloy gets traded to the Buffalo BillsCeltics: Marcus Smart gets traded to the Memphis GrizzliesRed Sox: Babe Ruth gets traded to the Yankees

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