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The Legacy of Theo Epstein: The Final Verdict

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With former Red Sox general manager Theo Epstein officially signed with the Chicago Cubs for the forseeable future, and Ben Cherington in charge of the Red Sox, I believe now is the perfect time for a true and fair reflection on Theo’s nine years of service for the tenants of Fenway Park.

While several media outlets have led a smear campaign against the onetime “young genius” of the Sox, I attempt to analyze the context of his decisions, and attempt to judge the ultimate impact that each of his decisions had during his run.

Sure, the young GM has had his faux pas, but he also had his successes, including bringing the Red Sox a pair of World Series titles during his tenure and reversing 86-years of futility. Below I present both the good and bad of the Theo Epstein era, and a final verdict on his time on Yawkey Way.

The Good


When Epstein began his Red Sox career in November 2002, the then 28-year-old retooled a roster that had missed the playoffs for three consecutive seasons. During that offseason, Epstein signed David Ortiz, Kevin Millar and Bill Mueller in free agency, all of which were major contributors to the their first World Series title.

The Red Sox offense had a dramatic turnaround during that 2003 campaign, scoring 961 runs (102 more than the previous season). Boston advanced to their first ALCS since 1999, but lost Game 7 on an Aaron Boone extra-inning walk-off home run.

Realizing that a lack of rotation depth and sufficient closer marred the team from their ultimate goal, Epstein convinced then-Diamondbacks’ starter Curt Schilling on Thanksgiving 2003 to accept a trade to Boston. Epstein also signed Athletics’ closer Keith Foulke as a closer to fix the ninth inning hole caused by his “closer-by-committee” experiment during 2003. Despite an atrocious start that had the team 9.5 games behind the Yankees on July 22, 2004, the Boston GM needed just one more change to turn the team into a championship contender during that famous 2004 season.

At the trading deadline, Epstein traded away Nomar Garciaparra, a franchise legend and fan favorite, for Expos’ SS Orlando Cabrera, Twins 1B Doug Mientkiewicz, and also acquired OF Dave Roberts from the Dodgers in a separate deal. The Red Sox went 42-18 the rest of the way to qualify for the post-season for the second straight year.

Boston swept Anaheim in the Divisional Round, and rallied from a 3-0 deficit to New York in the ALCS to advance  to their first Fall Classic since 1986. The Cardinals’ proved no issue for the Red Sox, who swept St. Louis to win their first World Series championship since 1986.


Following the atrocious 2006 campaign, Epstein once again retooled a roster on the brink of championship contention. Ownership opened the checkbook, so Epstein signed outfielder JD Drew, SS Julio Lugo, and pitchers Daisuke Matsuzaka and Hideki Okajima to strengthen to team. Dustin Pedroia was called up from the minors, and raked after a tough April.

The team was dominant all season, finishing 96-66 and clinching home field advantage over the Cleveland Indians. Boston again swept the Angels in the Divisional Round, and faced off against the Indians for the pennant.

Cleveland jumped out a 3-1 series lead, but Josh Beckett pitched a fantastic Game 5 to bring the series back to Boston. Jacoby Ellsbury, a September rookie stud, was inserted into the lineup and provided immediate dividends to the offense. Offseason acquisitions J.D. Drew and Matsuzaka were vital in Games 6 and 7, respectively, sending the Red Sox to their second Fall Classic in four years.

Boston easily dispatched the Rockies in a another sweep, with Mike Lowell, another aspect of the Josh Beckett trade,  getting MVP honors.

2008 was another difficult season for the team, but the Red Sox managed to earn the American League Wild Card with a 95-67 season. Curt Schilling missed the entire year with an injury, while Manny Ramirez’s shenanigans finally evicted him from the locker room. Ramirez was shipped to the Dodgers in a three-team deal that saw the Red Sox acquire Jason Bay at the trade deadline.

Boston trounced the Angels in four games in the Divisional round, but battled the rejuvenated Tampa Bay Rays in the ALCS. The team climbed out of another 3-1 hole to force a Game 7, but Matt Garza and David Price outdueled Jon Lester to take the series finale 3-1 to advance the Rays to their first ever World Series and end the Red Sox season.

The Bad


Following the championship performance in 2004, Epstein changed directions with a myriad of key players hitting free agency. Pedro Martinez and Orlando Cabrera signed with the Mets and Angels, respectively, while Curt Schilling’s ankle injury limited him to just 93-1/3 innings and a 5.69 ERA.

Edgar Renteria replaced Cabrera at shortstop, but was ineffective from day one, while World Series hero Mark Belhorn struggled and was released at mid-season. Theo tried to improve the rotation by bringing in Matt Clement and David Wells, but both pitchers could not put together an effective, complete season. Boston went 95-67, but was swept by the eventual champion Chicago White Sox.

Epstein had a tumultuous offseason, resigning on October 31, 2005, and even wearing a gorilla suit to avoid reporters. The Red Sox shipped Renteria to Atlanta for then-stud prospect Andy Marte that winter. Marte was later part of the package that was used to acquire Coco Crisp.

The Red Sox biggest move that offseason was the blockbuster trade that brought Marlins’ starter Josh Beckett to Boston. The team shipped off Hanley Ramirez, Anibal Sanchez and two other prospects. The Red Sox also acquired future 2007 World Series MVP Mike Lowell in the deal prior to Epstein rejoining the front office.

The moves proved to be fruitless however, as Boston battled a rash of injuries en route to an injury-riddle 86-76 record and a missed postseason.


The Red Sox went into 2009 will a deteriorating roster and several question marks long-term. Epstein once again made a July 31st splash by trading for Victor Martinez from the Indians to help accommodate a declining Jason Varitek, but the roster was not deep enough for a postseason run. Boston clinched the Wild Card, but were finally eliminated by the Angels in the Divisional Round in a three-game sweep.

Epstein decided not to retain Jason Bay, but picked up Martinez’s option and signed Anaheim starter John Lackey. Unfortunately for Boston, the 2010 season was marred by an 11-12 start, and an injury-plagued roster that saw significant playing time from Darnell McDonald, Daniel Nava, Bill Hall, and Eric Patterson. Boston finished 89-73, seven games behind in the division and six in the wild card.

It was a busy offseason for the front office with Victor Martinez leaving via free agency, Adrian Gonzalez coming to Fenway Park in a December trade, and a surprise signing of Carl Crawford to man the Green Monster.

Boston again struggled in 2011, getting off to a 2-10 start, but they became one of the best teams in the league from that point until the end of August. Despite struggles from Crawford and Lackey, the team possessed a nine-game lead on the postseason heading into the final month. At that point, the Red Sox collapsed by going 7-20 in September, and rumored clubhouse turmoil has plagued the Boston sports’ landscape ever since. Manager Terry Francona left, Epstein signed with Chicago, while John Lackey was ruled out for the 2012 season for Tommy John Surgery.

The Verdict

Regardless of having zero postseason wins in the last three seasons and an ugly divorce from the team, Theo Epstein will be remembered as the man who assembled a pair of World Series titles, including the first one in 86 years. While he certainly had his mistakes (and some were colossal), the fact is that no team in Major League Baseball has more than one title since 2001 (St. Louis could change that in this year’s World Series).

Epstein will now look to change the fortunes of another plagued franchise, the Cubs, who have a talented roster but are a few pieces away. Franchise cornerstones like Aramis Ramirez and Starlin Castro are key to the future success of Chicago, but it is how Epstein will morph the rest of the franchise that will determine his fate in the Windy City.

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2 comments for “The Legacy of Theo Epstein: The Final Verdict”

  1. […] Sports of Boston analyzed Theo Epstein’s legacy with the Red Sox. […]

    Posted by Baseball Blogs Weigh In: Lowe, Hanley, Frasor | Forex News | November 4, 2011, 6:34 pm
  2. A truly enept piece of writing…at least he seemed to have spell checked

    Posted by paul | November 4, 2011, 7:06 pm

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