The 8 Best And 7 Worst Moves In Boston Red Sox History

The Boston Red Sox are one of the most storied franchises in American Sports. It wasn't until the 21st century when people started to take note of it, though.

When the team traded Babe Ruth in 1919, the franchise embarked on an 86-year World Series drought. The team was so good for so many years in the '70s, '80s and '90s, but they were never good enough to break through and capture the championship. But after a series of big moves in the late '90s and early 2000s, the Red Sox became THE team of baseball. They've won three World Series championships since 2004 -- only the San Francisco Giants have as many.

Boston has since been one of the model American sports organizations, but it's amazing to think they have been a lot more successful over the decades. A series of terrible trades and awful free agent signings have prevented the Red Sox from accomplishing more.

Here is a look at the eight best and seven worst moves in Red Sox history.

Continue scrolling to keep reading

Click the button below to start this article in quick view

Start Now

15 Best: Trading For Dennis Eckersley

Gregory J. Fisher-USA TODAY Sports

Dennis Eckersley was coming off a breakout year with the Cleveland Indians in 1977, but the team opted to trade him to the Boston Red Sox in exchange for four solid veterans (namely Rick Wise and Mike Paxton). The deal worked out well for both sides, but Boston probably came out on the better end of it.

In his first year with the Red Sox, Eckersley went 20-8 with a 2.99 ERA and 162 strikeouts. The following season, he went 17-10 with another 2.99 ERA and 150 strikeouts. Eckersley did struggle down the stretch, as he lost speed on his fastball and eventually found himself traded to the Chicago Cubs in 1984.

But Eckersley provided the Red Sox with a much-needed ace, and he delivered big time with a pair of Cy young-caliber seasons at a low cost.

14 Worst: Signing Edgar Renteria

via myredsoxtoday.com

On paper, signing Edgar Renteria to widen the chances of repeating as World Series champions seemed great for the Red Sox. Renteria was coming off an excellent 2014 season with the St. Louis Cardinals that saw him bat .287 with 72 RBI, 17 stolen bases and a respectable 1.8 WAR. After beating his Red Birds in the 2004 World Series, Boston signed Renteria to a four-year deal worth $40 million.

Renteria batted just .276 -- his worst since 2001, struck out 100 times, had a .385 slugging percentage and posted a WAR of just 1.1. Those were all among some of the worst totals he posted in years. The Red Sox traded him after one year in Beantown to the Atlanta Braves in exchange for Andy Marte.

13 Best: Acquiring Jason Varitek And Derek Lowe

David Butler II-USA TODAY Sports

The Boston Red Sox acquired Heathcliff Slocumb in 1995 after reaching his first All-Star Game as a member of the Philadelphia Phillies. But the Red Sox chose to end the relationship early by dealing him to the Seattle Mariners in 1997 for catcher Jason Varitek and starter Derek Lowe. Slocumb was out of the Emerald City after 1998 and the Red Sox got two franchise cornerstones.

Varitek became one of baseball's best hitting catchers and was a three-time All-Star. He batted .270 or better in four different seasons and had a trio of 20 home run seasons in Beantown. He posted a 3.7 WAR in the Red Sox' 2004 World Series-winning season and played with the team until 2011. Lowe was a two-time All-Star with Boston and posted a remarkable 21-win season in 2002. He also won 14 games in 2004 and went 3-0 in the postseason to help the BoSox win their first World Series in 86 years.

12 Worst: Trading Jon Lester For Yoenis Cespedes

Winslow Townson-USA TODAY Sports

John Lester was the Red Sox' best starting pitcher during his time in Beantown from 2006 to 2014. He was a three-time All-Star and helped them win the 2007 and 2013 World Series. Lester won 15-plus games in five seasons with the Red Sox, too.

But Boston was among the worst teams in baseball during the 2014 season despite winning the 2013 World Series. With Lester set to become a free agent, they traded him and Jonny Gomes to the Oakland Athletics for Yoenis Cespedes, who was among the American League's best hitters and defensive outfielders.

Boston had hoped that Lester would rejoin them in the offseason, but he signed with the Chicago Cubs instead. Cespedes was later traded for Rick Porcello, which has turned out nicely for Boston. But they could have gotten more for Lester; or even kept him and agree to an extension before he hit the market.

11 Best: Trading For Josh Beckett And Mike Lowell

Bob DeChiara-USA TODAY Sports

The Red Sox were obviously unhappy with their inability to defend their World Series championship in 2005. So they went out and acquired star pitcher Josh Beckett and elite third baseman Mike Lowell (Pictured Holding Commissioner's Trophy), along with Guillermo Mota, for Hanley Ramirez, Anibal Sanchez and two other players.

This was another trade that worked out for both sides, but Boston benefited more. Beckett went 16-11 in his first year with the Red Sox and followed it up with a 20-win season in 2007, helping the Red Sox win the World Series. He was among baseball's top pitchers during his time in Boston. As for Lowell, he batted .270 or better in four of his five seasons in Beantown. Lowell had 21 home runs, a career-best 120 RBI, .324 batting average and 4.7 WAR in 2007, giving the Red Sox their second World Series in four years.

10 Worst: Signing Pablo Sandoval

Dan Hamilton-USA TODAY Sports

After a miserable 2014 season, the Red Sox tried to get back into playoff contention by handing out mammoth contracts to Hanley Ramirez and Pablo Sandoval. The jury is out on if Ramirez's contract was worth it, but so far Sandoval's has been a disaster. The three-time World Series champion with the San Francisco Giants signed a five-year, $95 million deal with Boston in the winter of 2014.

In 2015, Sandoval batted .245 with a .292 OBP, .366 slugging percentage and .658 OPS with a negative 0.9 WAR. Those were all the worst totals of Sandoval's career. He came back in 2016 looking to bounce back. Instead, injuries limited him to just three games. Sandoval didn't get a single hit in six at bats and spent plenty of the 2016 offseason trying to lose weight. We'll see if Panda can make the last three (?) years worth it.

But for now, he's on the list.

9 Best: The Nomar Garciaparra Trade

via thesportspost.com

Nomar Garciaparra was the face of the Red Sox franchise in the late '90s and early 2000s. But the Red Sox opted to make a gutsy trade at the 2004 trade deadline by sending the fan favourite to the Chicago Cubs. In a four-team trade, the Red Sox acquired Orlando Cabrera and Doug Mientkiewicz from the Minnesota Twins.

Cabrera became a huge part of the Red Sox' success in 2004. He batted .294 and hit 31 RBI in just 58 games played, posting an incredible 1.7 WAR in such short time. He batted .288 in the postseason and registered 11 RBI, becoming a key piece of their World Series-winning team. Mientkiewicz struggled in his short stint with Boston, but filled out a need at first base and did bat .444 in the postseason, winning a World Series ring.

8 Worst: Trading Jeff Bagwell

Troy Taormina-USA TODAY Sports

The Red Sox drafted Jeff Bagwell (Pictured Left), a Boston native himself, in the 1989 Draft. But the Red Sox were in an intense playoff race during the 1990 season and traded away the super prospect to the Houston Astros for reliever Larry Andersen. The latter didn't disappoint in Boston, posting a 1.23 ERA, 0.95 WHIP and 1.2 WAR in just 15 appearances. But Andersen joined the San Diego Padres the following season, and Boston saw Bagwell turn into one of baseball's biggest superstars.

In 15 MLB seasons with Housotn, Bagwell batted .297 with 2,314 hits, 449 home runs and 1,529 RBI. Bagwell was the 1994 National League MVP and reached four All-Star Games. Bagwell was one of the top first basemen, and Boston never found a guy at the position as talented after the trade. He was inducted into the Baseball Hall of Fame in 2017.

7 Best: Trading For Pedro Martinez

Greg M. Cooper-USA TODAY Sports

Pedro Martinez was a superstar with the Montreal Expos from 1994 to 1997, winning the World Series in his final season north of the border. But with Martinez due for a big payday, the Expos didn't want to lose him for nothing. He got traded to the Boston Red Sox for Carl Pavano and Tony Armas Jr. Martinez went 19-7 with a 2.89 ERA and 251 strikeouts in 1998.

He followed it up in 1999 with a 23-4 record, 2.07 ERA, 313 strikeouts and 9.5 ERA. Martinez would go on to win two AL Cy Youngs in Beantown, and cemented his legacy with the franchise in the 2004 postseason. Martinez went 2-1 during the playoffs with 26 strikeouts, and pitched a nearly-flawless Game 7 of the 2004 ALCS against the Yankees. It helped Boston win the 2004 World Series.

6 Worst: Signing Carl Crawford

Kirby Lee-USA TODAY Sports

Carl Crawford was one of baseball's top outfielders during his days with the Tampa Bay Rays. Crawford was a four-time All-Star and won the 2010 Gold Glove and Silver Slugger Award. He helped the Rays win the 2008 AL Pennant and 2010 AL East banner. But Crawford couldn't pass on a big payday from the Red Sox, and signed a seven-year contract worth $142 million in the 2010 offseason.

After hitting .300 or better in five of his last six years, Crawford batted a career-worst .255. His .289 OBP was also the worst of his career, and Crawford struck out a ridiculous 104 times in 506 plate appearances. Crawford's .694 OBS was also disappointing, considering it was above .800 the previous two seasons.

Crawford posted a WAR of 0.0, meaning Boston would have been just as good without him. In the midst of a disappointing 2012 season, he was part of a blockbuster/salary dump move and got traded to the Los Angeles Dodgers. That ended a forgetful 1.5 years in Boston.

5 Best: Trading For Manny Ramirez

Jayne Kamin-Oncea-USA TODAY Sports

Manny Ramirez was an accomplished superstar with the Cleveland Indians for eight years. Coming off an impressive 2000 season, ManRam entered free agency. Despite heavy offers from the Indians, Mariners and Yankees, Ramirez signed an eight-year deal worth $160 million with the Red Sox. They wouldn't regret a penny of it.

Ramirez batted .300-plus in five seasons with Boston, and batted .292 or better in the other three. In six of his eight years with the Red Sox, Ramirez hit at least 30 home runs and 100-plus RBI. His WAR was 4.0 or better in five different seasons as well. Ramirez was a cornerstone of the team's 2004 and 2007 World Series championship teams. Even though it was a hefty contract, the Red Sox spent $160 million perfectly.

4 Worst: Trading Curt Schilling And Brady Anderson

via boston.com

Before Curt Schilling and the Bloody Sock became iconic in Boston, some may forget that he began his MLB career as a prospect in the team's farm system. Schilling and fellow future All-Star Brady Anderson were traded to the Baltimore Orioles in 1988 for Mike Boddicker, who spent just three seasons in Beantown.

Meanwhile, Schilling became one of baseball's most dominant pitchers -- reaching five All-Star Games, winning a World Series with Arizona in 2001, leading the league in wins twice and winning 14-plus games in seven different seasons. It wasn't until 2004 when he would join Boston (more on that later). As for Anderson, he was a three-time All-Star and finished with a career .256 batting average with 210 home runs and 761 RBI. Not exactly a great trade for Boston.

3 Best: Bringing Back Curt Schilling

via baseballhall.org

Looking for another star pitcher to help out Pedro Martinez, the 2003 AL runner ups traded four players to the Diamondbacks for Schilling. None of those four players blossomed into stars, while Schilling was the final piece Boston needed to finally end their World Series drought.

He didn't disappoint in his first season with the Red Sox, going 21-6 with a 3.26 ERA, 1.06 WHIP, 203 strikeouts and an insane 7.5 WAR. He went 3-1 in the 2004 postseason with a 3.57 ERA. That bloody sock game against the New York Yankees in Game 6 of the 2004 ALCS forever enshrined the legacy of Schilling.

Schilling was inconsistent in 2005 but bounced back with a 15-7 record in 2006. He would retire a World Series champion in 2007, going 9-8 in the regular season. Schilling's career technically started in Boston; and he finished it perfectly as a champion where it all started.

2 Worst: Trading Babe Ruth

via sportsonearth.com

Sure, the Red Sox have three World Series championships since 2004, but they basically let their arch-rivals, the New York Yankees, become the most historic and successful team in American sports. All it took was former owner Harry Frazee to sell Babe Ruth to the Yankees in 1919 for $100,000. This was despite Ruth leading Boston to a trio of World Series championships and dominating as one of baseball's elite pitchers and batters.

Everyone knows this story. If Ruth was never sold to the Yankees, then Fever Pitch -- starring Jimmy Fallon and Drew Barrymore -- never takes place. Ruth won four World Series rings with the Yankees and helped them become the most successful franchise that is currently enjoying 27 World Series rings.

It's a rarity to trade the best player in the league at any given time, but Boston paid the price for 86 years while the Yankees cherish this trade nearly a century later.

1 Best: Signing David Ortiz

Bob DeChiara-USA TODAY Sports

The world has seen very few things as sweet and beautiful as Big Papi's home run swing.

David Ortiz was a forgotten commodity with the Minnesota Twins, and after being released in the 2002 season, feared he wouldn't be able to play baseball again. Ortiz signed a minor contract where he would have "made" $1.25 million if he "made" the team.

14 years later, Ortiz led the Red Sox to World Series championships in 2004, 2007 and 2013. Almost every clutch Red Sox' postseason home run in the 21st century has Ortiz's name on it. Big Papi was a 10-time All-Star, seven-time Silver Slugger Award winner and led the AL in RBI three times. His 483 home runs are second in franchise history; only Ted Williams had more. His .290 batting average places him 26th in Red Sox' history, and his 1,530 RBI are the third-most in team history.

Safe to say, Boston made the right call taking a chance on Big Papi, who is easily one of the greatest players in the city's history.

More in MLB