9 Worst Trades in Massachusetts Sports History

Trading for Kevin Garnett brought the Celtics a championship and getting Randy Moss propelled the Patriots to a 16-0 regular season.

While there are plenty of famous trades for Massachusetts sports teams over the years, not all have gone according to plan. These are the nine worst trades MA franchises have made.

1. Red Sox trade Babe Ruth for cash

The Babe Ruth deal is perhaps the most infamous trade in Massachusetts sports history. It dramatically altered the trajectory of both franchises involved.

Early in his legendary career, Ruth was an excellent pitcher for the Boston Red Sox, posting multiple 20-win seasons and leading the league in ERA during the 1916 season. Over his tenure in Boston, the Sox had great success, racking up three World Series titles.

While the team was performing well on the field, owner Harry Frazee had fallen into debt due to a failed theatrical production venture. So in early 1920, Boston shipped Ruth to the New York Yankees for $100,000 in cash to help finance the musical No No Nanette, and the rest is history.

Ruth became one of the most fearsome sluggers the sport has ever seen, guiding the Yankees to four World Series titles and ultimately propelling the Yankees to become the most successful team in the sport’s history.

After the trade, the Red Sox suffered over eight decades of misery and heartbreak over a period known as the “Curse of the Bambino.”

2. Bruins ship Thornton to San Jose

In 2005, shortly after signing all-star center Joe Thornton to a three-year extension, the struggling Boston Bruins decided to abruptly change course by shipping him to San Jose for a package that included Marco Sturm, Brad Stuart and Wayne Primeau.

Stuart and Primeau were shortly flipped to Calgary for valuable pieces while Sturm put up 193 points over five solid seasons. However, it was quickly apparent that Boston got the significantly shorter end of the stick.

Thornton exploded upon his arrival in San Jose during the 05-06 season, putting up 92 points in just 58 games with the Sharks en route to winning the Art Ross Trophy (leading scorer) and Hart Trophy (MVP). All told, Thornton posted over 1,000 career points after the trade, ranking him among all-time contemporary greats such as Sidney Crosby and Alex Ovechkin.

3. The infamous 1985 Patriots draft

While there weren’t a lot of successful seasons for the Patriots before the Bill Belichick era, their run to the 1985 Super Bowl stands out.

Lost in the shuffle of their success that year was the draft that preceded it, which involved one of the biggest “what ifs” in NFL history. The Patriots had the 16th overall selection that year, but without any glaring needs to address, they traded back to an eager San Francisco team for the 28th overall pick and a second and third-rounder.

The Niners turned that 16th overall pick into a wide receiver from Mississippi Valley State University by the name of Jerry Rice, who would go on to become the most prolific target the league has ever seen.

Over his illustrious 16-year career, Rice posted more than 1,500 receptions, close to 23,000 receiving yards and more than 200 touchdowns.

Check the current Patriots Super Bowl odds.

4. Bruins unload Dryden to rival Montreal; Dryden unloads back

The Bruins selected Ken Dryden during the 1964 draft but flipped him shortly after as part of a package for Guy Allen and Paul Reid.

If you are a bit fuzzy on who Allen and Reid are, it’s because neither of them ever played in a single NHL game. On the other hand, Dryden went on to have one of the most remarkable (albeit short) careers in NHL history.

Dryden lost just 57 total games during his seven seasons with Montreal while logging 46 shutouts. He won the Vezina Trophy five times and the Stanley Cup six times, eliminating the Bruins during four separate postseasons.

Check the current Bruins Stanley Cup odds.

5. Red Sox trade Bagwell for relief help

Boston native Jeff Bagwell was drafted by his hometown team in 1989 but never played a game for them. That’s because Boston flipped him at the trade deadline for a reliever by the name of Larry Andersen to shore up the bullpen.

The Red Sox wound up finishing in third place in the AL East that season, missing out on the playoffs by six games. Andersen would leave during the offseason as a free agent.

Jeff Bagwell could have become one of the great Massachusetts sports players of all time. Instead, he would become the face of the franchise in Houston, slugging 449 home runs en route to a Hall of Fame career.

6. Impatient Celtics flip Billups

Chauncey Billups was selected with the third overall pick by Boston during the 1997 draft but would play only 51 games as a Celtic.

Coach and team president Rick Pitino shipped Billups (along with Dee Brown, Roy Rogers and John Thomas) in exchange for Kenny Anderson, Popeye Jones and Zan Tabak. The Celtics would finish the season 10 games under .500.

While Anderson gave Boston some solid seasons, Billups would become a five-time all-star and help guide the Detriot Pistons to the 2004 NBA Title, winning Finals MVP. Not to mention, Billups would ultimately earn a reputation as one of the most clutch shooters in the NBA.

Check the current Celtics NBA Championship odds.

7. Patriots desperately reach for Sanu

While Bill Belichick is rightly lauded as one of the most brilliant on-field and front office minds in NFL history, he’s had his share of misfires over the years—none more so than when he overrated Mohamed Sanu.

Looking to get an aging Tom Brady some receiving help, Belichick uncharacteristically reached by trading a second-round pick in the 2020 draft. But Sanu never synced with the offense, logging just 207 yards and one touchdown in eight games before he was cut.

8. Sox deal top prospects for Mike Boddicker

While competing for a playoff spot during the 1988 season, the Red Sox sent a pair of prospects named Curt Schilling and Brady Anderson to Baltimore for reliever Mike Boddicker.

While Boddicker did help the Red Sox in the short term as they won AL East titles in 1988 and 1990, the club failed to reach the World Series either season.

Schilling would win multiple Cy Young Awards over the next decade while leading two teams to the World Series. Brady Anderson became a three-time all-star over a successful 14-year career. While the Red Sox memorably reunited with Schilling during their 2004 World Series run, he could have been in Boston for his entire career.

Check the current Red Sox World Series odds.

9. Celtics swap Paul Westphal for Charlie Scott

Shortly after the 1974-75 season, the Celtics sent Paul Westphal and two second-round picks to Phoenix for three-time all-star Charlie Scott.

Unfortunately, this wound up as one of the worst trades the Celtics ever made. Ultimately, it involved two players heading in opposite directions. Scott’s scoring average was 24.8 points per game before the trade but dipped to 17.5 during his Celtics tenure. Westphal took his game to another level, making five all-star appearances in six seasons with the title-contending Suns.

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