Boston Red Sox General Manager Theo Epstein: Boy Wonder or Just Lucky?

William PenfieldCorrespondent IIJune 23, 2011

Boston Red Sox General Manager Theo Epstein
Boston Red Sox General Manager Theo EpsteinElsa/Getty Images

Theo Epstein, is he a boy wonder or is has he just been lucky?

Ever since his hiring on Nov. 25, 2002 at the ripe age of 28, Epstein has been praised as the next big thing among general managers in Major League Baseball. He has accomplished some amazing feats as general manager of the Boston Red Sox, breaking the 86-year "Curse of the Bambino" in 2004, but has had some head-shaking blunders as well.

So how good of a general manager is Theo Epstein really? Does he deserve all the praise he gets in the baseball community?

Epstein has had some great signings in his tenure as general manager of the Boston Red Sox. The biggest, to date, has probably been David Ortiz, one of the biggest bargains in baseball during his time with the Red Sox.

In his eight full seasons with the Red Sox, Ortiz has earned just $69,837,000—a lot of money, but compared to baseballs other top-tier hitters such as Alex Rodriguez, who has earned $208,389,252, Ortiz has been a huge bargain for Epstein and the Red Sox. With what Ortiz did for the Red Sox in the 2004 playoffs alone, Epstein gets an A+ for the signing.

Other notable Epstein transactions include luring Curt Schilling away from the Arizona Diamondbacks for pennies on the dollar, pitchers Casey Fossum, Brandon Lyon and Jorge De La Rosa along with a minor league player to be named later. This trade could go down as one of the all time steals in MLB history with Fossum, Lyon and De La Rosa never amounting to much and Schilling leading the Red Sox to a World Series victory in 2004.

Epstein should also be praised for trading away young, "can't miss" prospects to obtain a veteran to help win the World Series as he did trading Casey Kelly for current first baseman Adrian Gonzalez. All though not GM at the time, Epstein played a large roll in the trade involving Red Sox top prospects Hanley Ramirez and Anibal Sanchez for Josh Beckett and Mike Lowell, the 2007 World Series MVP. Not all GM's would have the guts to pull the trigger on such deals. 

To go along with his successes, Epstein has had just as many, if not more, failures. Perhaps his biggest downfall being the inability to find a starting shortstop. Since the departure of Nomar Garciaparra in 2003, the Red Sox have had a plethora of shortstop's take the field, from Pokey Reese to Jed Lowrie to Edgar Renteria, Epstein has been unable to find a solid fit.

Epstein's two biggest mishaps at the shortstop position have been the signings of Renteria and Julio Lugo to long term deals. Renteria came first, signing a four-year $40-million deal after Orlando Cabrera departed for the Los Angeles Angels. He went on to commit a league high 30 errors and ended up being traded the following offseason for Andy Marte.

After a one year term for Alex Gonzalez, Epstein took another stab at finding his long term solution at shortstop, Julio Lugo. Lugo signed a four-year $36-million deal after the 2006 season and went on to hit just .242 with 42 errors in 266 games over three seasons for the Red Sox.

It would appear that the shortstop position is Epstein's "kryptonite" as a general manager but it seems as though he may finally have his man in Cuban-defector Jose Iglesias, currently playing for the Red Sox triple-a affiliate the Pawtucket Red Sox. Iglesias is said to already have gold glove defense at the shortstop position and if he can develop a major league bat, he could become an all-star as a big-leaguer.

Not far behind Epstein's shortstop mishaps is the signing of J.D. Drew to a five year $70-million deal in 2007. Drew was viewed as a can't miss player coming out of Florida State University, and in the beginning of his career, the hype seemed real. Drew peaked in 2006, the year before signing with the Red Sox, for the Los Angeles Dodgers, hitting .283 with 20 home runs and a 100 RBI to go along with a .393 OBP.

Epstein, enamored with OBP, jumped at the chance to sign Drew when he became a free agent after the 2006 season. Drew failed to live up to the hype in a Red Sox uniform failing to knock in more than 68 runs in four-plus years with the team.

Many have described Drew's attitude this season as disinterested as if he is set on retiring after the season and just laces up the cleats to cash a pay check. This perceived attitude and Drew's decreasing production has Red Sox Nation calling for his head. To put it in monetary terms, Drew will have made more money as a Red Sox, $70 million, in five seasons with the team as David Ortiz earned in eight seasons, $69,837,00, as previously mentioned.

Epstein may never admit it but he made a mistake signing Drew, a $70 million mistake but it may not be his biggest mistake. That mistake could end up being the signing of John Lackey to a 5-year $85.2-million deal in 2009. Lackey has been anything but stellar posting a mediocre 4.40 ERA with a 10-5 record in his first year with the team.

Lackey appears as if he could be headed towards a complete meltdown this season, currently with a 7.36 ERA and a 5-5 record and one of the most infamous sound bytes of the season with his quote, "Everything in my life sucks right now, to be honest with you," after he got shelled by the Toronto Blue Jays in the beginning of May. To this point Lackey has been a huge disappointment and potentially Epstein's worst signing ever. 

Epstein receives a failing grade for both his inability to find a long term fix at the shortstop position and J.D. Drew signing but gets an incomplete on the Lackey signing because it is possible, all though unlikely, that Lackey could turn his ailing career around in Boston. 

So is Theo Epstein a boy wonder? No. Does he deserve praise for winning two World Series championship's, bargain shopping for Ortiz and trading for the star veteran when need be? Yes, of course. Has he just got lucky on a few signings and trades? No, it takes a good GM to do the things that he has done. Does he also deserve criticism for his short comings? Definitely. Probably more than he has received but it is hard to complain about his results.