9 Worst Trades in Massachusetts Sports History

The acquisition of Kevin Garnett led the Celtics to a championship, while the addition of Randy Moss propelled the Patriots to a perfect 16-0 regular season.

Throughout the years, Massachusetts sports teams have witnessed numerous trades that have gained significant attention. However, it is important to note that not all of these trades have unfolded as intended. Here, we present a compilation of the nine most regrettable trades made by franchises in Massachusetts.

1. Red Sox trade Babe Ruth for cash

The trade involving Babe Ruth stands out as one of the most notorious deals in the history of Massachusetts sports. It had a profound impact on the future course of both teams involved.

In the early stages of his iconic career, Ruth established himself as an exceptional pitcher for the Boston Red Sox. He consistently achieved multiple 20-win seasons and secured the league’s best ERA in the 1916 season. Throughout his time with the team, the Red Sox experienced remarkable triumph, capturing three World Series championships.

Despite the team’s impressive performance on the field, owner Harry Frazee found himself in financial trouble after a theater production he invested in failed. As a solution, in early 1920, Boston decided to trade Ruth to the New York Yankees for $100,000 in cash. This transaction aimed to support the financing of the musical No No Nanette, and the rest, as they say, is history.

Ruth’s remarkable prowess as a slugger elevated her to the ranks of the sport’s most formidable players. Under her guidance, the Yankees clinched an impressive four World Series championships, ultimately establishing themselves as the most triumphant team in the history of the sport.

Following the trade, the Red Sox endured a period of more than eighty years filled with sorrow and despair, famously referred to as the “Curse of the Bambino.”

2. Bruins ship Thornton to San Jose

In 2005, right after agreeing to a three-year extension with all-star center Joe Thornton, the struggling Boston Bruins made an unexpected shift in direction by trading him to San Jose. The deal involved acquiring Marco Sturm, Brad Stuart, and Wayne Primeau.

Calgary acquired Stuart and Primeau in exchange for valuable assets, while Sturm demonstrated his prowess by accumulating an impressive 193 points in a span of five solid seasons. Nevertheless, it became evident that Boston had received the considerably inferior end of the deal.

During the 2005-2006 season, Thornton made a remarkable impact in San Jose, amassing an impressive 92 points in a mere 58 games with the Sharks. This outstanding performance led him to clinch both the Art Ross Trophy for being the top scorer and the Hart Trophy for being the most valuable player. Overall, Thornton’s career soared after the trade as he accumulated over 1,000 points, placing him alongside legendary players like Sidney Crosby and Alex Ovechkin.

3. The infamous 1985 Patriots draft

The Patriots didn’t have many successful seasons prior to the Bill Belichick era, but their journey to the 1985 Super Bowl is particularly notable.

The draft that took place before their successful year went unnoticed, overshadowed by their achievements. It featured one of the NFL’s most significant “what ifs”. Despite holding the 16th overall pick, the Patriots didn’t have any pressing areas to address. Consequently, they decided to trade it to an eager San Francisco team in exchange for the 28th overall pick, as well as a second and third-round selection.

Jerry Rice, a wide receiver hailing from Mississippi Valley State University, was acquired by the Niners through their 16th overall pick. Little did they know that Rice would go on to become the most dominant and record-breaking target in the history of the league.

Throughout his remarkable 16-year career, Rice accumulated an impressive record of over 1,500 receptions, nearly 23,000 receiving yards, and a remarkable tally of more than 200 touchdowns.

Please verify the current odds for the Patriots winning the Super Bowl.

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

During the 1964 draft, the Bruins picked Ken Dryden, but they promptly traded him as part of a deal that included Guy Allen and Paul Reid.

If you’re not familiar with Allen and Reid, it’s because they never had the opportunity to play a single NHL game. However, Dryden, on the contrary, had an exceptional (although brief) career that etched his name in NHL history.

During his tenure with Montreal, Dryden only experienced defeat in a mere 57 games across seven seasons, successfully recording 46 shutouts. His remarkable achievements include securing the Vezina Trophy five times and clinching the Stanley Cup on six occasions. Notably, Dryden emerged victorious against the Bruins in four different postseasons.

Please verify the present Stanley Cup odds for the Bruins.

5. Red Sox trade Bagwell for relief help

In 1989, Jeff Bagwell, a native of Boston, was selected by his hometown team in the draft. However, despite being drafted by them, he never had the opportunity to play a game for the team. This was due to a trade that occurred at the trade deadline, where Boston traded him in exchange for a reliever named Larry Andersen. The purpose of this trade was to strengthen the team’s bullpen.

That season, the Red Sox ended up in third place in the AL East, falling short of making the playoffs by a margin of six games. Subsequently, Andersen departed as a free agent in the offseason.

Instead of becoming one of the greatest sports players in Massachusetts history, Jeff Bagwell went on to become the iconic figure of the Houston franchise. He hammered 449 home runs during his outstanding career, ultimately earning a well-deserved spot in the Hall of Fame.

6. Impatient Celtics flip Billups

In the 1997 draft, Boston selected Chauncey Billups as the third overall pick. Despite his potential, Billups had a brief stint as a Celtic, playing only 51 games.

Rick Pitino, the coach and team president, traded Billups, Dee Brown, Roy Rogers, and John Thomas for Kenny Anderson, Popeye Jones, and Zan Tabak. As a result, the Celtics ended the season with a disappointing record, finishing 10 games below .500.

Although Anderson had a successful stint in Boston, Billups surpassed him by becoming a five-time all-star and leading the Detroit Pistons to win the 2004 NBA Championship, where he was also crowned Finals MVP. Additionally, Billups gained recognition as one of the NBA’s most reliable and clutch shooters.

Please examine the present odds for the Celtics’ chances of winning the NBA Championship.

7. Patriots desperately reach for Sanu

Despite being recognized as one of the greatest minds in NFL history when it comes to on-field strategies and front office decisions, Bill Belichick has made his fair share of errors throughout the years. One notable misjudgment was his overestimation of Mohamed Sanu.

In an uncharacteristic move, Belichick traded a second-round pick in the 2020 draft to provide some receiving support for the aging Tom Brady. However, Sanu failed to integrate well into the offense, managing only 207 yards and one touchdown in eight games before being released.

8. Sox deal top prospects for Mike Boddicker

In their pursuit of a playoff spot in the 1988 season, the Red Sox made a trade with Baltimore, sending two promising prospects named Curt Schilling and Brady Anderson in exchange for reliever Mike Boddicker.

Although Boddicker contributed to the Red Sox’s success by helping them secure AL East titles in 1988 and 1990, the team fell short of reaching the World Series in both seasons.

Over the course of the next ten years, Schilling would earn multiple Cy Young Awards and successfully guide two teams to the World Series. Anderson, on the other hand, enjoyed a prosperous 14-year career, earning the title of three-time all-star. Although the Red Sox famously reunited with Schilling during their 2004 World Series victory, it is worth noting that he could have potentially spent his entire career in Boston.

Please verify the current odds for the Red Sox in the World Series.

9. Celtics swap Paul Westphal for Charlie Scott

After the 1974-75 season, the Celtics traded Paul Westphal and two second-round picks to the Phoenix Suns in exchange for Charlie Scott, a three-time all-star.

Regrettably, this trade turned out to be one of the Celtics’ most disastrous moves. In the end, it resulted in two players heading towards completely different trajectories. Prior to the trade, Scott had an impressive scoring average of 24.8 points per game, but it declined to 17.5 during his time with the Celtics. On the other hand, Westphal elevated his game to new heights, earning five all-star selections in six seasons with the Suns who were vying for the championship title.

Related Pages:

• Massachusetts Sports History’s 7 Most Disastrous Contracts