Theo's Five Worst Free Agent Signings

The Red Sox have enjoyed an incredible amount of success since the organization made the decision to hire Theo Epstein as the General Manager in November of 2002.  Not only was the “curse of the Bambino” lifted during his reign, but the Sox managed to clinch a second World Series title and have been one of baseball’s best teams year after year. 

At the time of his hiring, Epstein was the youngest GM in the history of baseball.  But with age comes wisdom and if he were given the opportunity to go back and do a few things differently, I’m sure he would agree that these are a few he wished he would have avoided.

5.  Last week the Red Sox decided to designate veteran outfielder Mike Cameron for assignment.  This announcement signaled the surrender of Red Sox management on Cameron and kicks off this list of forgettable blunders. 

In the winter of 2009 Theo Epstein inked Cameron to a two-year, $15.5 million contract to try and fill the gaping hole that was left field for the Sox.  With the trade of Manny and the failure to re-sign Jason Bay, the move was a peculiar one that obviously has winded up backfiring and yielded minimal results.

During his short tenure with Boston, the 38-year-old has suffered a plethora of injuries and has only played in 81 games.  His pathetic .219 batting average is laughable and he’s only managed to hit a total of seven home runs and drive in 24 RBIs.  His recent demotion means he will either have to be traded or accept a minor league assignment (neither of which are very plausible scenarios).  Therefore the Sox will most likely be forced to cut him and then eat the rest of his remaining salary.

4.  Some Sox fans may not remember the name Matt Clement, but back in 2004 he signed a three-year $25 million contract and was projected to be an integral part of Boston’s rotation.  The plan went better than expected early on as Clement began the 2005 season 10-2 and made the American League All-Star team.  Unfortunately, it was all downhill from there.

Shortly after that all-star appearance, Clement was nailed by a screaming line drive and his psyche and mound skills never seemed to return to him.  From that point on he compiled an 8-9 record and only appeared in 12 games in 2006 before pitching in his final game for the Sox on June 14^th.  He ended his Sox career at 18-11 with underwhelming 5.09 ERA.

3.  The short stop position has been a point of much consternation during the Epstein regime and the search to replace Boston favorite Nomar Garciaparra has proven much more difficult than he originally anticipated.  However, Theo thought he had found the solution in 2006 when he employed Julio Lugo to man the position.

It was a four-year $36 million contract and his production certainly did not warrant such a substantial salary.  In his four years in Tampa prior to coming to Boston he showed some promise as his season averages were a .287 average with 10 HRs, 53 RBIs and 22 stolen bases.  In his entire time with the Sox (266 games) he batted .251 with a meager total of 10 HRs, 103 RBIs and 48 steals.  Given his mighty struggles the Red Sox found themselves in another Mike Cameron situation and ended up cutting him just to watch him eventually be snatched up by another team while Boston picked up the tab.

2.  Although this next player’s contract is not yet complete, it’s fair to say that by the end of next season Daisuke Matsuzaka’s time in Boston will be viewed as a monumental disappointment.  Out of all the potential free agent pitchers available in the ’06 offseason, none were surrounded with the type of hype that accompanied this Japanese star.

The six-year, $52 million contract is just the tip of the iceberg because the Red Sox had to fork out $51.1 million just to own the rights to negotiate with Dice-k.  So, in reality, the Sox basically signed him to a $103.1 million deal.  That is a ton of money to dole out for one good season.  Matsuzaka was 18-3 with a 2.90 ERA in 2008.  That effort placed him fourth in the Cy Young voting but also ultimately proved to be the ceiling of what was, at one point, a very hopeful, young talent.

After a subpar 2009 campaign he followed it up with two seasons of extensive DL stints (including season-ending surgery earlier this year).  With these displays of deterioration and patterns of significant decline, it’s difficult to imagine that 2012 will be any different, and it looks as though this will just have to be another one chalked up under the loss column.

1.  Let’s just say that 2006 wasn’t exactly Theo Epstein’s greatest year.  The final three players on this list were all signed within that timeframe.  Rounding out this undesirable group is another player whose time in Boston has yet to expire, but will be celebrated once that time arrives.  J.D. Drew was a number one overall draft pick who never quite lived up to the expectations that follow a prospect of that magnitude. 

Although he did have a couple good years prior to signing with the Sox, the five-year, $70 million contract has not been viewed favorably amongst the Fenway faithful.  Throughout his Red Sox career, Drew has never played in more than 140 games in any season and has never reached 500 at bats.  He is currently on pace to hit 8 HRs, knock in 36 RBIs and his average now sits at .231 for the season.  Those aren’t exactly the eye-popping stats that would be associated with a corner outfielder pulling in over $14 million a year.

Despite these shortcomings it’s very difficult to criticize Theo too harshly.  Even with overpaying Lugo, Dice-K and Drew he managed to field a championship team in 2007 and in his profession that is ultimately the only thing that matters.  Hindsight is always 20/20, so for whatever few poor decisions have been made, the good decisions have far outnumbered the bad. His dedication and proven track record make it easy for Red Sox nation to place their trust in his hands and there’s no reason not to believe that as long as he remains in the front office that this will be the status quo for many years to come.