Boston Red Sox: Theo Epstein's 10 Worst Decisions as General Manager

Adam MacDonald@adammacdoAnalyst IIJune 3, 2011

Boston Red Sox: Theo Epstein's 10 Worst Decisions as General Manager

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    BOSTON, MA - DECEMBER 11:  Theo Epstein, general manager of the Boston Red Sox, answers questions about Carl Crawford during a press conference on December 11,  2010 at the Fenway Park in Boston, Massachusetts.  (Photo by Elsa/Getty Images)
    Elsa/Getty Images

    Some people rave about Theo Epstein. He is the young, handsome, Yale-educated wunderkind who masterminded two World Series championships and finally broke the Curse.

    It is true he has made some good moves. The signing of Jon Lester and Dustin Pedroia to relatively low-paying contracts has worked out great. He also acquired Adrian Gonzalez without giving up any notable major-league players.

    But there are other decisions that have not worked out so well for Epstein and the Red Sox. Here, we take a look at 10 of the worst.

Why Eric Gagne Is Not on This List

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    BOSTON - OCTOBER 24:  Eric Gagne #83 of the Boston Red Sox pitches in the ninth inning of Game One of the 2007 Major League Baseball World Series against Colorado Rockies at Fenway Park on October 24, 2007 in Boston, Massachusetts.  (Photo by Jed Jacobsoh
    Jed Jacobsohn/Getty Images

    Gagne was an unmitigated disaster. He had a 1.88 WHIP and an earned run average of 6.75 in 18 innings after he was acquired from Texas.

    But in 33.1 IP with the Rangers, Gagne had been great, with an ERA of just 2.16. The Red Sox were making a run at the postseason, and while they were not crying out for bullpen help, another arm is always good. The reasons behind the trade were sound; the end result was borderline embarrassing.

The Gorilla Suit

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    FORT MYERS, FL - FEBRUARY 19:  General Manager Theo Epstein of the Boston Red Sox watches the team during a Spring Training Workout Session at the Red Sox Player Development Complex on February 19, 2011 in Fort Myers, Florida.  (Photo by J. Meric/Getty Im
    J. Meric/Getty Images

    On October 31, 2005, Theo Epstein resigned as GM, only to return two-and-a-half months later. In his absence, incidentally, the Red Sox acquired Josh Beckett and Mike Lowell from the Florida Marlins, a move Theo probably would have been loathe to make since it meant parting with prospect Hanley Ramirez.

    The fact he resigned and returned is a little unusual, but there is nothing wrong with it. Epstein's crime was driving away from Fenway Park dressed in a gorilla costume to avoid the press and fans. Just as Doug Mirabelli's police escort is still a source of derision, Theo's Hallowe'en dress-up is still a ridiculous, sorry chapter in his tenure as GM.

    However, there are no photos of him in the suit. Alas.

Letting Alex Gonzalez Leave

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    BOSTON - AUGUST 18:  Alex Gonzalez #11 of the Boston Red Sox is late with the tag as Bobby Abreu #53 of the New York Yankees safely steals second on August 18, 2006 at Fenway Park in Boston Massachusetts.  (Photo by Jim McIsaac/Getty Images)
    Jim McIsaac/Getty Images

    Theo Epstein has struggled to find a solution at shortstop. He had fan favourite Nomar Garciaparra but traded him at the deadline in 2004. He was replaced with former Expo Orlando Cabrera, who was electric in the postseason en route to Boston’s first championship in 86 years. Then began the revolving door.

    Edgar Renteria, Alex Gonzalez, Alex Cora, Julio Lugo, Nick Green, Jed Lowrie and Marco Scutaro have all tried their hand at short, and none has entrenched himself at the position. Lowrie has made the best stab at it of late, but his time there will not last long with Jose Iglesias coming up through the minors.

    The best shortstop the Red Sox had in that time was Gonzalez. Offensively, he was poor. Very poor. But with the glove, one could argue that there was no one better in the game. Epstein let him walk too.

Edgar Renteria

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    CHICAGO - OCTOBER 05:  Shortstop Edgar Renteria #3 of the Boston Red Sox throws to first base for an out against the Chicago White Sox during the first inning of Game Two of the American League Division Series at U.S. Celluar Field on October 5, 2005 in C
    Jonathan Daniel/Getty Images

    Speaking of shortstops, we have Edgar Renteria.

    The Sox looked set with Orlando Cabrera—who is still playing well in Cincinnati—but they let him walk after 2004 and traded for Renteria.

    He was not atrocious like Gagne, but he was far from good. A .276 average, his lowest home run total in seven years and seven stolen bases (75 percent below his career average) was not what Theo had envisioned, and Renteria did not return for 2006.

J.D. Drew

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    BOSTON, MA - APRIL 12:  J.D. Drew #7 of the Boston Red Sox reacts after he struck out in the bottom of the ninth inning as Kelly Shoppach #10 of the Tampa Bay Rays catches on April 12, 2011 at Fenway Park in Boston, Massachusetts. The Tampa Bay Rays defea
    Elsa/Getty Images

    Is there a more infuriating player in baseball today than J.D. Drew? He has everything you could want as a player: a good team, a great contract and bucketloads of talent. The problem is he doesn’t care.

    Or, at least, he does not appear to. Drew just never seems to give it his all when he is on the field. He is not on the field as often as you would like either, since he has asked out of games with "hamstring tightness" or "a sore neck" more times than one can count. With Boston he has never hit 25 home runs in a season, and his high in RBI is 68.

    But he had that grand slam against Cleveland in 2007, right? So he must be worth the $14 million a year.

Letting Alex Gonzalez Leave Again

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    NEW YORK - SEPTEMBER 27:  Alex Gonzalez #3 of the Boston Red Sox fields the ball against the New York Yankees on September 27, 2009 at Yankee Stadium in the Bronx borough of New York City.  (Photo by Jim McIsaac/Getty Images)
    Jim McIsaac/Getty Images

    Fool me once, shame on you. Fool me twice, shame on me.

    The Red Sox knew exactly what they were missing in Gonzalez and brought him back in 2009. Again, he performed well, but Epstein elected not to sign him after the season. The next year, he hit career highs in home runs (23) and RBI (88) with Toronto.

Julio Lugo

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    ANAHEIM, CA - MAY 14: Shortstop Julio Lugo #23 of the Boston Red Sox plays in the field against the Los Angeles Angels of Anaheim on May 14, 2009 at Angel Stadium in Anaheim, California.   The Angels won 5-4 in 12 innings.  (Photo by Stephen Dunn/Getty Im
    Stephen Dunn/Getty Images

    .251 average, 10 home runs and 101 batted in. That would be bad for one season, but those are Lugo’s totals in his three years in Boston. That stellar production cost the Red Sox $35.6 million.

Mike Cameron

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    BRADENTON, FL - MARCH 13:  Outfielder Mike Cameron #23 of the Boston Red Sox throws the ball in against the Pittsburgh Pirates during a Grapefruit League Spring Training Game at McKechnie Field on March 13, 2011 in Bradenton, Florida.  (Photo by J. Meric/
    J. Meric/Getty Images

    You have a good center fielder in Jacoby Ellsbury and a spare $9 million a year in the bank. What do you do? Of course, you go out and sign 37-year-old CF Mike Cameron.

    For short money and as a backup, that is a fine signing. But no. Theo Epstein inked him to a two-year, $18 million deal and moved Ellsbury to left, with the intention of bringing him back to CF in a few years’ time.

    It did not make sense then. It makes even less now. Cameron was injured last year and has been terrible in 2011. Quelle surprise.

John Lackey

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    ANAHEIM, CA - APRIL 24:  John Lackey #41 of the Boston Red Sox throws a pitch against the Los Angeles Angels of Anaheim on April 24, 2011 at Angel Stadium in Anaheim, California. The Red Sox won 7-0.  (Photo by Stephen Dunn/Getty Images)
    Stephen Dunn/Getty Images

    Sure, it is early days. Last year, with his 4.40 ERA, Lackey was awful but could just have been acclimatising to a new team and new division. This year, his wife is battling breast cancer, and playing baseball is probably the last thing he wants to do.

    It is still a terrible signing, though, especially to a five-year, $82.5 million contract.

Letting Victor Martinez Leave

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    NEW YORK - SEPTEMBER 24:  Jonathan Papelbon #58 of the Boston Red Sox meets with Victor Martinez #41 during the ninth inning against the New York Yankees on September 24, 2010 at Yankee Stadium in the Bronx borough of New York City. The Red Sox defeated t
    Andrew Burton/Getty Images

    We all thought Victor was going to command a huge contract when he was a free agent last winter. In the end, he signed a rather tame four-year, $50 million deal with the Detroit Tigers.

    He was not going to be able to catch for much longer, of course; Detroit is using him as a full-time DH right off the bat. But he could have taken over the DH role when David Ortiz left or even just platooned at catcher for a few years.

    A part-time Victor Martinez, who had the highest batting average against lefties in all of baseball last year, or a part-time Jarrod Saltalamacchia: Which would you rather have?

Daisuke Matsuzaka

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    ANAHEIM, CA - APRIL 23:  Daisuke Matsuzaka #18 of the Boston Red Sox throws a pitch against the Los Angeles Angels of Anaheim on April 23, 2011 at Angel Stadium in Anaheim, California.  (Photo by Stephen Dunn/Getty Images)
    Stephen Dunn/Getty Images

    Matsuzaka has brought the Red Sox quite a lot (and no, not just a migraine). In terms of marketing and sponsorship he has been a valuable commodity. He had a brilliant 18-3 record and 2.90 ERA in 2008 and at times since then has shown glimpses of his potential to be a dominant pitcher in North America.

    Unfortunately, he is the only player who would rival J.D. Drew for the title of "most infuriating." He takes ages to throw a pitch, and when he does, he is afraid of throwing strikes. He could go out and pitch a one-hitter but five days later give up seven runs in the first inning. Even with the off-the-field upside, he has not been worth the $100 million investment.