Theo Epstein’s Moves: Good and Bad

Theo Epstein spent 10 years as general manager of the Red Sox, and while he brought the team two World Seires championships, did have a few questionable moves along the way. Here are some of his most famous moves, both the good and the bad.
Theo's Moves
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Theo Epstein spent 10 years as general manager of the Red Sox, and while he brought the team two World Seires championships, did have a few questionable moves along the way. Here are some of his most famous moves, both the good and the bad.
The Yankees reliever was one of Epstein's first signings with the Red Sox, and did not work out as planned. After inking a two-year, $6.5 million deal, Mendoza was part of the failed bullpen by committee experiment, and finished his two years in Boston 5-6 with a 5.73 ERA.
Ramiro Mendoza
(Photo by Ezra Shaw/Getty Images)
The Yankees reliever was one of Epstein's first signings with the Red Sox, and did not work out as planned. After inking a two-year, $6.5 million deal, Mendoza was part of the failed bullpen by committee experiment, and finished his two years in Boston 5-6 with a 5.73 ERA.
Mueller was brought in before the 2003 season, and made a much bigger impact than expected. He ended up winning the 2003 batting crown, and was a solid contributor to the 2004 World Series team.
Bill Mueller
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Mueller was brought in before the 2003 season, and made a much bigger impact than expected. He ended up winning the 2003 batting crown, and was a solid contributor to the 2004 World Series team.
Epstein signed Mike Timlin off the scrap heap in 2003, and the righty reliever helped solidfy the Red Sox bullpen for the next six seasons. He played a pivitol role in the 2004 World Championship, and finished his career in Boston with a 3.76 ERA.
Mike Timlin
(Photo by Stephen Dunn/Getty Images)
Epstein signed Mike Timlin off the scrap heap in 2003, and the righty reliever helped solidfy the Red Sox bullpen for the next six seasons. He played a pivitol role in the 2004 World Championship, and finished his career in Boston with a 3.76 ERA.
After the heartbreaking loss in the 2003 playoffs, Epstein went out and landed the Red Sox another pitching ace in Curt Schilling. Schilling become a Red Sox legend for years to come after helping the Red Sox win two World Series titles in his four years in Boston.
Curt Schilling
(Photo by Al Bello/Getty Images)
After the heartbreaking loss in the 2003 playoffs, Epstein went out and landed the Red Sox another pitching ace in Curt Schilling. Schilling become a Red Sox legend for years to come after helping the Red Sox win two World Series titles in his four years in Boston.
After it was apparent Boston needed a closer, Epstein courted Keith Foulke before the 2004 season. The two attended a Celtics game together, and Foulke ended up signing a three-year, $18.75 million contract. He pitched 14 innings in the 2004 postseason, and was on the mound when the Red Sox finally won the World Series. Although he was never the same after the 2004 playoffs, Foulke's performance was a big part in the Red Sox winning it all.
Keith Foulke
(Photo by Stephen Dunn/Getty Images)
After it was apparent Boston needed a closer, Epstein courted Keith Foulke before the 2004 season. The two attended a Celtics game together, and Foulke ended up signing a three-year, $18.75 million contract. He pitched 14 innings in the 2004 postseason, and was on the mound when the Red Sox finally won the World Series. Although he was never the same after the 2004 playoffs, Foulke's performance was a big part in the Red Sox winning it all.
Late in the 2003 free agency period, Epstein signed Twins DH David Ortiz. While the Red Sox were not expecting much out of Ortiz, he hit 31 homers and drove in 101 runs in just 128 games played. Ortiz went on to be one of Boston's most clutch hitters, and has enjoyed a nine-year career as one of the faces of the franchise.
David Ortiz
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Late in the 2003 free agency period, Epstein signed Twins DH David Ortiz. While the Red Sox were not expecting much out of Ortiz, he hit 31 homers and drove in 101 runs in just 128 games played. Ortiz went on to be one of Boston's most clutch hitters, and has enjoyed a nine-year career as one of the faces of the franchise.
In 2004, Epstein sent Shea Hillenbrand to the Arizona Diamondbacks for closer Byung-Hyun Kim. While Kim did not work out, the move allowed Bill Mueller to take over at third base full-time, and David Ortiz to slide into the DH position.
Shea Hillenbrand
(Photo credit: JOHN MOTTERN/AFP/Getty Images)
In 2004, Epstein sent Shea Hillenbrand to the Arizona Diamondbacks for closer Byung-Hyun Kim. While Kim did not work out, the move allowed Bill Mueller to take over at third base full-time, and David Ortiz to slide into the DH position.
At the 2004 deadline, Theo sent prospect Henri Stanley to the Dodgers for utlility outfielder Dave Roberts. Roberts provided speed on the bases, and came up with one of the biggets plays of the 2004 World Series run.
Dave Roberts
(Photo by Ezra Shaw/Getty Images)
At the 2004 deadline, Theo sent prospect Henri Stanley to the Dodgers for utlility outfielder Dave Roberts. Roberts provided speed on the bases, and came up with one of the biggets plays of the 2004 World Series run.
In his boldest moves as Red Sox GM, Epstein sent disgruntaled Red Sox star Nomar Garciaparra to the Cubs, along with Matt Murton, and received Orlando Cabrera from the Expos at the 2004 trade deadline. Cabrera's defense and attitude in the clubhouse helped spark Boston's late season run, and helped propel them to their first World Series in 86 years.
Orlando Cabrera
(Photo by Al Bello/Getty Images)
In his boldest moves as Red Sox GM, Epstein sent disgruntaled Red Sox star Nomar Garciaparra to the Cubs, along with Matt Murton, and received Orlando Cabrera from the Expos at the 2004 trade deadline. Cabrera's defense and attitude in the clubhouse helped spark Boston's late season run, and helped propel them to their first World Series in 86 years.
After Epstein decided not to re-sign Orlando Carbrera, he signed Renteria to a four-year, $40 million contract. In his only season in Boston, Renteria hit just .276 and had 30 errors, and was traded to the Atlanta Braves for prospect Andy Marte, with the Red Sox eating a lot of the contract.
Edgar Renteria
(Photo by Jim McIsaac/Getty Images)
After Epstein decided not to re-sign Orlando Carbrera, he signed Renteria to a four-year, $40 million contract. In his only season in Boston, Renteria hit just .276 and had 30 errors, and was traded to the Atlanta Braves for prospect Andy Marte, with the Red Sox eating a lot of the contract.
Clement was signed to a three-year, $25 million contract after the departure of Pedro Martinez. Clement made the All-Star team in his first season with Boston, going 10-2 before the break, but finished the season at 13-6 with a 4.57 ERA. He was struck in the head by a line drive in July, and was never the same. He finished his two seasons in Boston with a 18-11 record and 5.09 ERA.
Matt Clement
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Clement was signed to a three-year, $25 million contract after the departure of Pedro Martinez. Clement made the All-Star team in his first season with Boston, going 10-2 before the break, but finished the season at 13-6 with a 4.57 ERA. He was struck in the head by a line drive in July, and was never the same. He finished his two seasons in Boston with a 18-11 record and 5.09 ERA.
In March of 2006, Epstein sent pitcher Bronson Arroyo to the CIncinnatti Reds for slugger Wily Mo Pena. While Pena was expected to bring some more pop to the middle of the Boston lineup, he struggld mightily at the plate, he hit just 11 home runs in 84 games while batting .301. He was traded to the Washington Nationals after batting .218 over 73 games in 2007.
Wily Mo Pena
(Photo by Jim McIsaac/Getty Images)
In March of 2006, Epstein sent pitcher Bronson Arroyo to the CIncinnatti Reds for slugger Wily Mo Pena. While Pena was expected to bring some more pop to the middle of the Boston lineup, he struggld mightily at the plate, he hit just 11 home runs in 84 games while batting .301. He was traded to the Washington Nationals after batting .218 over 73 games in 2007.
Epstein long coveted Julio Lugo, and signed the short stop to a four-year, $36-million contract before the 2007 season. In his first season in Boston, Lugo hit just .237 in 147 games. He had 19 errors in 2007, and followed that up with 16 in 81 games in 2008. Lugo was traded to the St. Louis Cardinals for Chris Duncan in 2009 with Boston eating most of his remaining contract. Lugo finished his Red Sox career batting .251 with 103 RBI in two and a half seasons.
Julio Lugo
(Photo by J. Meric/Getty Images)
Epstein long coveted Julio Lugo, and signed the short stop to a four-year, $36-million contract before the 2007 season. In his first season in Boston, Lugo hit just .237 in 147 games. He had 19 errors in 2007, and followed that up with 16 in 81 games in 2008. Lugo was traded to the St. Louis Cardinals for Chris Duncan in 2009 with Boston eating most of his remaining contract. Lugo finished his Red Sox career batting .251 with 103 RBI in two and a half seasons.
Theo and crew pulled out all the stops to sign Japanese pitching sensation Diasuke Matsuzaka. After posting a $51 million bid just to talk with Matsuzaka, the Red Sox signed him to a six-year, $52 million contract.  After going 33-15 in his first two seasons with the Red Sox (including 18-3, 2.90 ERA in 2008), Matsuzaka is just 16-15 the last three years while battling various injuries and control issues. Matsuzaka had to undergo Tommy John Surgery last season, and is not expected to return to the club until August at the earliest.
Daisuke Matsuzaka
(Photo by Darren McCollester/Getty Images)
Theo and crew pulled out all the stops to sign Japanese pitching sensation Diasuke Matsuzaka. After posting a $51 million bid just to talk with Matsuzaka, the Red Sox signed him to a six-year, $52 million contract. After going 33-15 in his first two seasons with the Red Sox (including 18-3, 2.90 ERA in 2008), Matsuzaka is just 16-15 the last three years while battling various injuries and control issues. Matsuzaka had to undergo Tommy John Surgery last season, and is not expected to return to the club until August at the earliest.
To fill the void left by Johnny Damon's depature to the Yankees, Epstein traded Guillermo Mota, Andy Marte, Kelly Shoppach and Cash to the Indians for Coco Crisp, Dave Riske and Josh Bard. While Crisp never filled Damon's shoes, he spent three seasons in Boston, playing great defense in center field.
Coco Crisp
(Photo by Jim Rogash/Getty Images)
To fill the void left by Johnny Damon's depature to the Yankees, Epstein traded Guillermo Mota, Andy Marte, Kelly Shoppach and Cash to the Indians for Coco Crisp, Dave Riske and Josh Bard. While Crisp never filled Damon's shoes, he spent three seasons in Boston, playing great defense in center field.
Epstein signed Bobby Kielty in August of 2007 to give the Red Sox outfield a bit more depth as they made their postseason run. Kielty did not do much, but in his only at bat during the 2007 World Series, hit a solo home run late in Game 4 on the only pitch he saw, which went on to be the game-winning run in the 4-3 victory.
Bobby Kielty
(Photo by Stephen Dunn/Getty Images)
Epstein signed Bobby Kielty in August of 2007 to give the Red Sox outfield a bit more depth as they made their postseason run. Kielty did not do much, but in his only at bat during the 2007 World Series, hit a solo home run late in Game 4 on the only pitch he saw, which went on to be the game-winning run in the 4-3 victory.
Drew signed a five-year, $70-million contract before the 2007 season.  He will forever be remembered for his Game 6 grand slam agains the Indians in the 2007 ALCS, but never lived up to his big dollar contract. He played in 606 games over five seasons (his 140 in 2007 were the most in a season while with Boston) and finished his Red Sox career with a .264 batting average with 80 home runs and 286 RBI.
JD Drew
(Photo by J. Meric/Getty Images)
Drew signed a five-year, $70-million contract before the 2007 season. He will forever be remembered for his Game 6 grand slam agains the Indians in the 2007 ALCS, but never lived up to his big dollar contract. He played in 606 games over five seasons (his 140 in 2007 were the most in a season while with Boston) and finished his Red Sox career with a .264 batting average with 80 home runs and 286 RBI.
After finally having enough Manny Ramirez' antics, Epstein sent him to the LA Dodgers at the 2008 trade deadline in a three-team deal, landing Jason Bay with the Red Sox. Bay hit .274, clubbing 45 home runs with the Sox in his season and a half in Boston, but was not re-signed when his deal expired.
Jason Bay
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After finally having enough Manny Ramirez' antics, Epstein sent him to the LA Dodgers at the 2008 trade deadline in a three-team deal, landing Jason Bay with the Red Sox. Bay hit .274, clubbing 45 home runs with the Sox in his season and a half in Boston, but was not re-signed when his deal expired.
Penny signed a one-year, $5 million deal for the 2009 season. After starting 5-1 in his first 10 starts, Penny 2-7 before being released in August. He ended his Red Sox career with a 7-8 record and a 5.61 ERA.
Brad Penny
(Photo by Jim Rogash/Getty Images)
Penny signed a one-year, $5 million deal for the 2009 season. After starting 5-1 in his first 10 starts, Penny 2-7 before being released in August. He ended his Red Sox career with a 7-8 record and a 5.61 ERA.
Pineiro was signed to a one-year, $4 million deal for the 2007 season to help the Red Sox bullpen. In 34 innings pitched, Pineiro allowed 20 runs and 41 hits for a 5.03 ERA. He was let go mid-season, and went 6-4 for the Cardinals in 11 starts.
Joel Pineiro
(Photo by Jim McIsaac/Getty Images)
Pineiro was signed to a one-year, $4 million deal for the 2007 season to help the Red Sox bullpen. In 34 innings pitched, Pineiro allowed 20 runs and 41 hits for a 5.03 ERA. He was let go mid-season, and went 6-4 for the Cardinals in 11 starts.
At the 2009 trade deadline, Epstein traded Justin Masterson, Nick Hagadone and Bryan Price to the Cleveland Indians for catcher/first baseman Victor Martinez. Martinez spent a season and a half with the Red Sox, batting .313 with 28 homers and 128 RBI.
Victor Martinez
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At the 2009 trade deadline, Epstein traded Justin Masterson, Nick Hagadone and Bryan Price to the Cleveland Indians for catcher/first baseman Victor Martinez. Martinez spent a season and a half with the Red Sox, batting .313 with 28 homers and 128 RBI.
Epstein got lucky when third baseman Adrian Gonzalez agreed to a one-year, $10 million deal before the 2010 season. Beltre was one of the more productive offensive players during the injury plagued season for Boston, batting .321 with 28 homers and 102 RBI.
Adrian Beltre
(Photo by Otto Greule Jr/Getty Images)
Epstein got lucky when third baseman Adrian Gonzalez agreed to a one-year, $10 million deal before the 2010 season. Beltre was one of the more productive offensive players during the injury plagued season for Boston, batting .321 with 28 homers and 102 RBI.
Instead of signing Jason Bay, Epstein and the Red Sox gave 37-year old Mike Cameron a two-year, $15.5 million deal. This moved Jacoby Ellsbury to left field, where he got hurt, and relied on Cameron to be the very day center fielder. He only played in 48 games, batting .259. He was released by the Sox during the 2011 season.
Mike Cameron
(Photo by J. Meric/Getty Images)
Instead of signing Jason Bay, Epstein and the Red Sox gave 37-year old Mike Cameron a two-year, $15.5 million deal. This moved Jacoby Ellsbury to left field, where he got hurt, and relied on Cameron to be the very day center fielder. He only played in 48 games, batting .259. He was released by the Sox during the 2011 season.
Epstein signed Crawford to a monster seven-year, $142 million dollar deal last winter. Crawford did not live up to the big dollars though in his first season in Boston, batting just .255 with 11 homers and 56 RBI. He hit nearly everywhere in the Red Sox lineup, but saw most of his time at their number-eight hitter.
Carl Crawford
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Epstein signed Crawford to a monster seven-year, $142 million dollar deal last winter. Crawford did not live up to the big dollars though in his first season in Boston, batting just .255 with 11 homers and 56 RBI. He hit nearly everywhere in the Red Sox lineup, but saw most of his time at their number-eight hitter.
Epstein sent four prospects to San Diego to get Gonzalez, who signed a seven-year, $154 million contract extension with his new team. Gonzalez thrived in Fenway Park, setting career highs in batting average (.338), hits (213) and runs scored (108) in his first year in Boston. He stuggled at the end of the season, but finished with 27 home runs and 117 RBI.
Adrian Gonzalez
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Epstein sent four prospects to San Diego to get Gonzalez, who signed a seven-year, $154 million contract extension with his new team. Gonzalez thrived in Fenway Park, setting career highs in batting average (.338), hits (213) and runs scored (108) in his first year in Boston. He stuggled at the end of the season, but finished with 27 home runs and 117 RBI.
Epstein found a gem off the scrap heep, signing Alfredo Aceves to a one-year, $650,000 deal. Aceves was one of the more steady arms on the Boston pitching staff, alllowing just 37 runs in 114 innings pitched. He finished the year 10-2 with a 2.61 ERA, mostly seeing time out of the bullpen. Aceves also made four starts during the season, and by the end of the year had teammates pushing for his spot in the starting five.
Alfredo Aceves
(Photo by Ed Zurga/Getty Images)
Epstein found a gem off the scrap heep, signing Alfredo Aceves to a one-year, $650,000 deal. Aceves was one of the more steady arms on the Boston pitching staff, alllowing just 37 runs in 114 innings pitched. He finished the year 10-2 with a 2.61 ERA, mostly seeing time out of the bullpen. Aceves also made four starts during the season, and by the end of the year had teammates pushing for his spot in the starting five.
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