The Most Heartbreaking Trades in Boston History

By Shawn Dennis

If there’s one thing that New Englanders love more than iced coffee in the middle of January, it’s their sports. Once an athlete on any Boston team shows a glimpse of being legendary, has that gritty side, or plays above the rest, Bostonians flood the stores and buy all the apparel associated with them. 

There’s too many players to use as examples. From Tom Brady to Larry Bird to David Ortiz to Patrice Bergeron, die hard New England sports fans have been blessed by so many greats and hall of famers alike that have made each franchise into a dynasty. At the end of the day, professional sports is a business and regardless of how much fans love their favorite players, they get traded from time to time. 

Some trades were necessary in order to build for the future, while others have left fans scratching their heads for years wondering what the hell the GM was thinking. 

Here’s a list of the five most heartbreaking trades throughout the decorated history of New England sports. 

5. Mookie Betts traded to the Los Angeles Dodgers- February 11, 2020.

Is it tradition to trade the best player on the Red Sox on the century mark since Babe Ruth? Although the implications and reasonings for trading Mookie makes sense when you analyze the money that involves both him and the Sox, it was still as shocking as it was difficult to bear. A season where Mookie batted .346 in 2018 and having the 9th banner hung in Fenway Park, not a single Sox fan wanted to see him play for another team. To make matters worse, Betts went on to lead the Dodgers to win the World Series just two years later. Bittersweet is an understatement. 

If the Red Sox would’ve traded any other player on their roster, then fans wouldn’t have been nearly in as much of an uproar. This may be obvious, but looking at how star-studded the team was at the time, it makes a lot of sense to say that. The worst part about the entire exchange, aside from the fact that he went to a Boston rival in LA, Mookie pleaded that he wanted to retire in a Red Sox uniform.

4. Tyler Seguin traded to the Dallas Stars- July 4, 2013

Following the Boston Bruins Stanley Cup defeat to the Chicago Blackhawks back in 2013, the B’s had a solid core of guys that could easily bring them back to the Finals the following year. One of those key players in the run was 21-year-old centerman Tyler Seguin, who had arguably the brightest future out of any young player on the team. Seguin had played during the 2011 Stanley Cup victory for the Bruins as a rookie and acquired a ton of playoff experience during his first three seasons. 

For what it’s worth, Boston was too concerned with “off the ice” issues that Seguin was dealing with and were looking for a veteran to help run the Bruins offense instead. That led to the 7-player-trade with the Dallas Stars that centered around Tyler Seguin and Loui Erikkson. Now, Erikkson definitely had his fair share of great performances for the Bruins, but the impact that Seguin had for Dallas was insurmountably greater. 

In his first season in 2014 for the Stars, Seguin went on to score 37 goals and tally 47 assists in 80 games. He instantly fit right in the Stars rotation and this led to Bruins fans being in a frenzy towards what general manager Peter Chiarelli was thinking. To trade the second pick in the 2010 Draft after three seasons that were all played above-average and had certainly lived up to the expectations given from being such a high prospect, the Bruins should’ve held onto the star.

3. Isaiah Thomas traded to the Cleveland Cavaliers- August 22, 2017

This trade had so many mixed emotions swirled into it. Isaiah Thomas was a two-time All-Star in Boston and played his heart out every time he stepped on the TD Garden floor. Not a single Cetlics fan will ever forget the day that Isaiah’s younger sister, Chyna Thomas, died in a car accident a day prior to the first game of the first round in the 2017 playoffs against the Chicago Bulls. Thomas went on to drop 33 points in the opener, and although they lost the game, that performance will go down as one of the greatest in Celtics history. This was the same season that IT was a single-point behind Larry Bird for the highest average of points per game for a Celtics player with 28.93. We often forget just how good “the little guy” was. 

For what Boston received in return, the trade was a no-brainer. Yes, Kyrie Irving only played two seasons for the Celtics and had fans hopes way too high due to the words he was feeding the media in relation to his future in Boston, but Danny Ainge almost couldn’t turn down that trade. Especially knowing the health of IT and Kyrie heading into his prime years. That’s what makes this trade more heartbreaking in the grand scheme of things because of what IT brought for the fans, what he done for Boston, and what Kyrie was supposed to do for the C’s, which was hang up banners with Jayson Tatum, along with retiring his own #11 jersey. Not build a superteam over in Brooklyn. 

  1. Paul Pierce and Kevin Garnett traded to the Brooklyn Nets- June 28, 2013

When you first look at this trade, it seems Danny Ainge was making a terrible move because of how much Paul Pierce and Kevin Garnett gave for the Boston Celtics. If anyone had bled green for that team during the unforgettable 2008 Championship series against Kobe Bryant and the Los Angeles Lakers, it was Pierce and KG, and that’s the truth. Kevin Garnett was a staple in Boston, as the Celtics haven’t had a big that’s come anywhere close in filling his shoes. Paul Pierce stuck around through the Boston rebuild and created such a legendary team built around him.

However, Ainge needed to clear cap space considering the Big Three was coming to an end and the quick rebuild ignited upon this trade. And what a trade it turned out to be. 

Some make the argument that it may actually be the worst trade of all time because of the assets that came from the draft picks and pick swap in 2017. Two All-Stars with Jayson Tatum and Jaylen Brown, which is such a lopsided return due to the fact that Paul Pierce played a single season for the Nets, Jason Terry did virtually nothing for them, and KG averaged career-lows in just about every category for the three half-played seasons in Brooklyn.

So, for as much as all of Boston hated seeing the Big Three break, all good things eventually come to an end and this was the best way it could’ve panned out. Aside from Ray Allen signing with the Miami Heat to win a championship with LeBron in 2013, that one still doesn’t sit well in BeanTown. 

  1. Babe Ruth sold to the New York Yankees for $100,000- January 5, 1920

If you haven’t heard of the name Babe Ruth, you’ve either been living under a rock or… yeah, there’s no other rhyme or reason not to know the most famous baseball player of all time. This is the trade of all trades where two of the greatest teams in sports collided and altered the future of both franchises because of it. Ruth led the Sox to back-to-back World Series wins in 1915 and 1916, won another in 1918, and went on to hit 714 home runs over the span of his 22 season career. He went on to win four more titles for the Yankees. 

The story behind the Ruth trade has been told all too many times, but true Red Sox fans will never get over losing one of, if not, the best baseball player ever to their rival for a whopping $100,000. Oh what could’ve been in Boston if Harry Frazee, the Red Sox team owner at the time, didn’t ruin the franchise for decades to come because of this trade and the many that followed in the 1920 season. 86 years to be exact, but who’s counting?

If you feel there’s been a trade that’s hurt more as a Boston fan from over the years, feel free to leave a comment or share your thoughts!

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