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Should Theo Epstein Be on the Hot Seat?

Theo Epstein At Press Conference (AP Photo/Elise Amendola)

(Disclaimer): I can already see your faces as you read this article title. I mentioned my planning to write this article to my roommate and I was met with instant dismissal. I would, however, like to point out that I am not advocating Theo’s firing, or even expressing a dislike for him. This article is merely meant to show readers that Theo is not as great of a General Manager as we all assume.

Theo Epstein has been the General Manager for the Boston Red Sox since 2002 (or if you count his brief resignation, since 2006). When Epstein was hired, he became the youngest GM in baseball history at the ripe old age of 28. Since his employment as GM, the Boston Red Sox have won two World Series titles, been to four AL Championship Series, and captured one AL East Championship.

Much of this success of the Red Sox comes from the new attitude brought in by owners John Henry, Tom Werner, and Larry Lucchino. They came in and brought a new attitude of winning to the Boston Red Sox organization. The Sox began to rival the Yankees in more than just the standings. The payroll for the Red Sox increased to a point where they had the second highest payroll, right behind the Evil Empire themselves.

This is where Theo comes in. As we have seen with the Yankees under the George Steinbrenner administration, spending lots of money on high profile free agents can help “buy” a World Series. It was not long until Theo was given a pretty hefty payroll to work with as well.

Theo’s Body of Work


Initially, Theo did not spend too much. He made a great signings in 2003 by signing David Ortiz, a not-yet aging Mike Timlin, and infielder Bill Mueller. Timlin proved to be a solid reliever for the Red Sox. Ortiz began to become the great hitter we know him as, and Mueller won the batting title. As we all know, however, the Red Sox lost to the Yankees in the ALCS that season.


Theo then started to break into the bank account. Realizing the team was in need of a closer, he signed free agent Keith Foulke to a three-year,  $20.25 million contract. In that same off-season, Theo made the first of his blockbuster trades that led the Red Sox to their first World Series title in 86 years. Theo traded Casey Fossum, Brandon Lyon, Jorge de la Rosa, and Michael Goss to the Arizona Diamondbacks for starting pitcher Curt Schilling. Schilling, teamed with Pedro Martinez, finally gave the Red Sox the 1-2 punch they needed in their starting rotation.

Theo did not stop there. With the Red Sox gearing up for the playoffs, Theo made quite possibly the second biggest trade in Red Sox history. Epstein traded the face of the franchise, Nomar Garciaparra, along with Matt Murton, and received Orlando Cabrera and Doug Mientkiewicz. On the surface, this trade did not look that appealing to Boston fans. Although Garciaparra was falling out of favor with the fans for his lack of team effort, he was still Boston’s Favorite Son.

However, after Foulke fielded Edgar Renteria’s grounder and tossed it to Mentkiewicz for the final out in the 2004 World Series, Epstein’s move looked genius. He had taken the former face of a franchise, a franchise searching for hope, and turned it into a World Series Championship.

Also worth noting, Theo acquired Dave Roberts in a separate deal to give the team desperately needed speed off the bench. After one critical stolen base in the ALCS, Roberts also made Theo look like a genius.

Instantly, Esptein became thought of as one of the best General Manager’s in all of baseball. The young, stud GM had just made one of the riskiest trades in baseball and turned a doubtful fanbase into the fans of the World Champion Boston Red Sox.

Fans stopped doubting Epstein. He was a genius in their eyes. Every move that Theo made was thought of as a good move because he must have known what he was doing. Hell, he brought this city a World Championship, something 95% of Red Sox fans had never known.


Then, Henry and Werner opened up the checkbook. Epstein started to spend more money because he could. He kicked off the free agent signing period by inking David Wells, Edgar Renteria, and Matt Clement to contracts. Theo also re-signed one of the keys to the championship, Jason Varitek, to a four-year, $40 million contract. Between those four, Theo spent $193.95 million dollars. Now, that number pales in comparison to the half billion dollars that the Yankees spent this past offseason, but $193.95 is still a lot of money.

The 2005 season for the Red Sox did not live up to the previous season. The Sox scooped up the Wild Card on their way to a three-game sweep at the hands of the Chicago White Sox. Epstein failed to make an impact trade during that season either. The Renteria signing failed. He struggled playing in a big market where there is always pressure to win. Matt Clement pitched decent, but nowhere well enough to live up to his contract. David Wells had a slightly better season than Clement, and with a much cheaper contract, it made the signing look a lot better.

The end of 2005 almost brought an end to the Theo Epstein-era in Boston. Following a contract dispute and an ownership dispute, Epstein left the team after rejecting a three-year, $4.5 million contract offer. The Red Sox front office was in turmoil, but assistant GMs Ben Cherington and Jed Hoyer took Epstein’s place.


The resignation of Epstein did not last long, and rumors are even though he was not with the team, he was still working with Cherington and Hoyer. During his unemployment, the Red Sox made several key trades.

Top prospect Hanley Ramirez was shipped off to Florida along with Anibal Sanchez, Harvey Garcia, and Jesus Delgado. In exchange, the Red Sox received pitching ace Josh Beckett, third baseman Mike Lowell, and reliever Guillermo Mota. This was the biggest trade the organization had made since the Nomar deal. The trade was highly regarded as a win-win for both squads, with the main pieces being Ramirez and Beckett.

The trades did not stop there. Tim Wakefield’s catcher, Doug Mirabelli, was shipped off to San Diego for Mark Loretta. Edgar Renteria, after one year in Boston, was traded to Atlanta for Andy Marte, who was thought of as a highly touted prospect.

Soon after those deals were made, Epstein made amends with the Red Sox organization and officially returned to the team as General Manager and Executive Vice President. As soon as Epstein sat back down at his desk, he began dealing again.

After letting Johnny Damon walk due to concerns about age, health, and playing ability, the Red Sox flipped newly acquired Andy Marte, Guillermo Mota, and top catching prospect Kelly Shoppach to Cleveland for Coco Crisp, David Riske, and Josh Bard. Crisp became the new starting centerfielder for the Red Sox, and Bard’s job was to take over catching duties for Wakefield. The Bard experiment failed, and he was shipped to San Diego along with Cla Meredith to bring back Doug Mirabelli.

Epstein had brought in some strong players in order to bring Boston back into the postseason. However, that plan did not work. The Red Sox struggled immensely, and ended up finishing third in the AL East. A lot of the failure had been chalked up to injuries, but some started to question Epstein’s skill as a GM.


Poised to end those thoughts, Epstein again decided to break the bank. Still without a solid starting shortstop, Epstein signed Julio Lugo to a four-year, $36 million dollar contract. Epstein then signed outfielder J.D. Drew to a five-year, $70 million contract to replace Trot Nixon.

Meanwhile, Japanese phenom Daisuke Matsuzaka decided that he wanted to play in the MLB. During the bidding process for the rights to negotiate with Matsuzaka, the Red Sox bid $51.1 million to win negotiation rights. On the eve of the signing deadline, the Red Sox and Matsuzaka agreed to a six-year, $52 million contract.

Between those three players, Epstein spent $158 million, plus the $51.1 million posting fee. The Red Sox began doing exactly what their rival Yankees did: spend a large sum of money and hope it brings them a World Championship.

Luckily for Theo (and Red Sox Nation), the Red Sox captured their second World Series title in four seasons. Epstein almost made a fatal mistake during the season, however. Eric Gagne had begun a career resurrection with the Texas Rangers. He was starting to pitch as effectively as he did as a member of the Los Angeles Dodgers. Epstein decided that he wanted Gagne to create an almost unbeatable set-up/closer combination of Gagne and Jonathan Papelbon.

Epstein pulled the trigger on a deal with the Texas Rangers that sent Kason Gabbard, David Murphy and Engel Beltre to the Rangers for Gagne. Gagne struggled for the Red Sox, giving up 14 runs in 14 innings pitched to go along with three blown saves. On the other hand, Murphy is playing well in Texas. The 27-year-old has a .278 batting average with 35 homeruns and 147 RBI in his career. Murphy also plays decent defense and could have been a solid, young fourth outfielder for Boston.

The Red Sox re-acquired Gabbard from the Rangers for cash considerations in 2009, meaning that the Gagne trade was essentially Murphy and Beltre for Gagne. However, this trade began the downfall in Theo’s effectiveness as a General Manager. Even though the Red Sox won the World Series in 2007, the sure-fire trade that Theo made almost prevented the Red Sox from winning the title.


Before the 2008 season, Theo decided not to make many moves. He re-signed the reigning World Series MVP, yet aging Mike Lowell, the even older Mike Timlin, the injured Curt Schilling, and knuckleballer Tim Wakefield. Resigning all of them broke the mold of the Red Sox organization. The team began to shy away from re-signing older players on the down slope of their careers.

Lowell has been solid since the start of the 2008 season, but he has been injured often. He has a bad hip, and that has hurt his level of production. He is a lot slower than he used to be, and is ineffective as an everyday player. Schilling did not throw a pitch in the 2008 season and has since retired. Timlin, who had already shown signs of wear and tear, had a terrible year, posting a 5.56 ERA in 47 appearances. Wakefield is the only exception, but he has been a solid contributor his entire career.

Theo made another big splash during the 2008 season. After Manny Ramirez proved to be too much of a distraction, he was traded to the Dodgers in a three-way deal that brought Jason Bay to Boston. The Red Sox also traded young, but struggling pitcher Craig Hansen and young outfielder Brandon Moss to the Pirates. Bay, currently a free agent, has flourished in Boston. Bay helped the Red Sox reach their fourth ALCS of the decade, but the Sox ultimately lost to the Rays in seven games.


The following off-season, Theo tried making a splash by signing one of the big name free agents available. However, Theo failed to sign CC Sabathia, Mark Teixeira, or A.J. Burnett. Instead, the Yankees were able to sign all three of those players. Epstein instead decided to go for low-risk contracts with other free agents. He signed Brad Penny, John Smoltz, and Rocco Baldelli to cheap, incentive-based contracts. Both Penny and Smoltz were cut by Boston due to their lack of production. Both players were thought of as low-risk, high-reward players, but instead they turned out to hurt the team more than help.

The 2009 season also saw the departure of Julio Lugo. Lugo was traded to the Cardinals for Chris Duncan, who the Red Sox later released. The Lugo trade showed another weakness in Epstein: his inability to find a full-time shortstop for the Red Sox. He later acquired Alex Gonzalez, which turned out to be a wise move.

However, Theo ended up making a huge impact at the trade deadline. Epstein was able to acquire Victor Martinez without giving up many of the Red Sox top prospects. Epstein did have to trade Justin Masterson to the Indians, who was the only true long reliever that the Red Sox had in the bullpen. The departure of Masterson did hurt the bullpen, but Martinez will be an offensive force for Boston for a long time, provided Epstein can retain him.

The Hot Seat

You may be asking yourself why I think Theo should be on the hot seat if I have not been too critical of him. The truth is that Theo has done a pretty solid job as the Red Sox General Manager. Epstein is an absolute genius when it comes to drafting. While the Red Sox still do trade for, or attempt to sign big name players, the team is loaded with home grown talent.

Epstein has drafted the 2008 AL MVP in Dustin Pedrioa, the Red Sox single season steals leader in Jacoby Ellsbury, a future ace in Clay Buchholz, and one of the most feared closers in Jonathan Papelbon.

So why the hot seat?

The entire Boston Red Sox front office runs under a mentality that they have to make the big move. The Red Sox did not have to go out and get Victor Martinez last season, because they already had an excess of corner infielders and designated hitters. The Martinez deal forced the Red Sox to sit one of Mike Lowell, Kevin Youkilis, and David Ortiz on most nights.

Theo also almost gave up their entire farm system in pursuit of potential franchise players. Epstein was willing to trade Buchholz along with some of the Sox’ top prospects in order to obtain Roy Halladay, Felix Hernandez, or Adrian Gonzalez.

Epstein has changed his mentality as General Manager. Instead of looking out for what is best for the team, he is trying to get big name players in order to one-up the Yankees. The Bay trade helped the team, but it has not brought a championship to Boston. The Martinez trade helped the offense out a little bit, but all that brought the city was a sweep at the hand of the Angels.

The bottom line is that Theo has made plenty of mistakes in his career, and he can afford to do so. If he makes a bad signing (i.e. Julio Lugo and potentially Matsuzaka) he can trade him away, eat the contract, and shrug it off because the Red Sox have the money to do so. Theo has made plenty of mistakes as GM that he has gotten away with.

I firmly believe that if the Red Sox do not make a move during Free Agency this offseason and either re-sign Bay or sign Matt Holliday, and then fail to bring home a championship, Epstein’s job could come into question. Although, as we all have seen as baseball fans, the managers are typically blamed before the front office.

Now that the city of Boston has to watch the New York Yankees bring home another World Series title, the pressure will be on for Theo to bring the Red Sox back to the World Series. If he cannot do that, his future as General Manager of the organization will come into question. Theo has to show he can build another championship winning team, because in Boston, anything less than first is unacceptable.

About A.J. Szczerbinski

I am a 20-year old sophomore at Bentley University in Waltham, MA. After living in Central Massachusetts my entire life, I moved to Northern Virginia. I've been a fan of the Red Sox and Celtics my entire life, but I also cheer for the Buffalo Bills and Sabres.

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4 comments for “Should Theo Epstein Be on the Hot Seat?”

  1. Should Theo Epstein Be on the Hot Seat?: (Disclaimer): I can already see your faces as you read this article title. …

    Posted by Sports of Boston | November 10, 2009, 1:32 pm
  2. Wow.
    Compare this statement:
    “Epstein has changed his mentality as General Manager. Instead of looking out for what is best for the team, he is trying to get big name players in order to one-up the Yankees.”
    With this one,two paragraphs later:
    “I firmly believe that if the Red Sox do not make a move during Free Agency this offseason and either re-sign Bay or sign Matt Holliday, and then fail to bring home a championship, Epstein’s job could come into question.”
    So what do you want? Do you want him to make a big move, or not? do you want him to spend a couple hundred million on guys who are now or have recently been at the top of their game? Do you want him to sign 35 year olds, or 25 year olds with promise but no track record? Truth is, a lot of moves don’t work out because of injuries, inability to play the big market, or what have you.
    I, for one, think Theo has his head on facing forward. It may not work out all the time, but even when it hasn’t worked out the team has still been in there for 95 plus wins and a crack at the season. Easy to second guess. So tell me, you tell me what he should do, how much he should spend, and we will judge you at the end of the season. How’s that???

    Posted by OW Holmes | November 10, 2009, 9:56 pm
  3. Should Theo Epstein Be on the Hot Seat? | Sports of Boston

    Posted by bigdreams1102 | November 10, 2009, 11:12 pm
  4. i think theo is the best gm in baseball, but all he needs is one impact player to get them to the top again

    Posted by Enice24 | November 11, 2009, 8:33 pm

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