Theo Epstein's 10 Worst Free Agent Signings with the Red Sox

Theo Epstein, the architect and GM of two World Championships, has been a master at his craft.

He has built the Boston Red Sox through the farm system and some of the gutsiest trades in Sox history.

But, he has shown flaws under his reign and the most glaring has been his free agent signings.

Epstein has had gems like David Ortiz, Mike Timlin and Bill Mueller.

Yet, he's whiffed on most of his signings.

Here is a look at the Top 10 worst free agent signings under his helm.

No. 10. Keith Foulke

Okay, I've gone back and forth on this one. I thought Keith Foulke didn't deserve to be on this list because of 2004. But, it was his complete meltdown after 2004 that he made this list.

What looked like a Theo Epstein coup, Foulke was signed by the Sox in the winter of 2003 to shore up a glaring hole for Boston.

Coming off Rolaids Reliever of the Year, Foulke saved 32 games for the Sox during their championship run of 2004 and should have won World Series MVP.

But, his impending meltdown the next season was hard to believe.

2005, Foulke had 15 saves and a 5.91 ERA and lost the closer role to Jonathan Papelbon in 2006.

Foulke spent '05 and '06 off and on the DL. He didn't help himself with the Boston fans referring to them a 'Johnny from Burger King'.

Foulke soon retired but now is pitching in the minors with the Newark Bears.

No. 9 Ramiro Mendoza

Coming off of four World Championships with the hated rival, New York Yankees, the versatile Mendoza was signed to help out a Sox bullpen.

Mendoza was thought to be useful to the Sox as a starter, long reliever and possibly a set up man.

Epstein missed.

Mendoza finished 2003 with a 3-5 record and an orbiting 6.75 ERA.

2004 seemed a little better with 2-1 record and a 3.75 ERA. Yet, injuries took a toll on Mendoza and he was left off of the 2003 and 2004 playoff roster.

Boston released him on Nov. 1 of 2004.

No. 8 J.C. Romero

The numbers were deceiving. 1-0 with a 3.15 ERA. What wasn't deceiving was his control. Fifteen walks to 11 strikeouts.

Thought to be the left-handed specialist that Epstein craved, Boston signed Romero before the 2007 season.

Too often Romero would come on and leave runners on base. Sox bullpen would have to bail him out.

Romero allowed 24 hits and the 15 walks in only 20 innings pitched.

He didn't even make to the All-Star break as Romero was released by the Sox on June 19, 2007.

Romero has since won a World Series with Philadelphia and was given a 50 game suspension for using PED's

No. 7 Julian Tavarez

Tavarez was coming off two successful years as a late inning pitcher for the St. Louis Cardinals. Epstein swooped in and signed Tavarez before the 2006 season for added bullpen help.

From there, the Boston nut-case, showed instability on the mound and in his head.

From 2004-2008, his ERA ballooned faster than Kirstie Alley:
2004- 2.38
2005- 3.34
2006- 4.47
2007- 5.15
2008- 6.39

Tavarez was used primarily as a sixth and seventh inning reliever for the Sox and when injuries decimated the Sox, he became their fifth starter.

But, too often Tavarez became unreliable on the mound and was eventually released on May 20, 2008.

No. 6 David Wells

Looking for a left-handed pitcher, Epstein sought out veteran David Wells to fill out an already shaky starting rotation in 2005.

Boomer went 15-7 with a 4.45 ERA, the highest he had since 1999, with Toronto.

The following year, Wells became more of a distraction and a hassle in the clubhouse. This is nothing new to Wells, but for the Sox, they looked to rid of the troubled clubhouse.

Wells spent most of his 2006 season with the Sox on the DL because he was out of shape and had shoulder issues.

With Boston in the midst of a lagging 2006, mostly due to injuries, Wells was shipped to San Diego for George Kotteras.

No. 5 Joel Piniero

With Jonathan Papelbon suffering from shoulder subluxation in September of 2006, Epstein went after Joel Piniero. The thought behind the signing was Piniero would become the closer for Boston and Papelbon would go back to starting.

How quickly that didn't work out.

During Spring Training of 2007, Piniero has getting hit harder than Ricky Hatton. Papelbon was tiring after the third inning of each of his Spring Training starts.

Papelbon pleaded his case to become the Sox closer and the rest was history.

Piniero became a seventh inning reliever for the Sox.

He pitched 31 games but was tattooed on the mound. He finished his Sox short stint with 5.03 ERA and was subsequently traded to St. Louis for the infamous, 'payer to be named later'.

No. 4 Matt Clement

With Pedro Martinez taking off to the Mets and Derek Lowe going to the West Coast for the Dodgers, Epstein needed to re-tool his pitching staff.

Theo went out and signed Matt Clement for the 2005 season.

Clement got off to an unbelievable start with the Sox, going 10-2 with a 3.85 ERA and making the All Star team.

Then on July 26, 2005, Clement was beaned in the head with a line drive, in Tampa. Clement recovered but was never really the same. He went 3-3 with a 6.00 ERA the rest of the way and was shelled in his only outing of the 2005 playoffs.

2006 was a disaster for Clement, as he went 5-5 with a 6.61 ERA, before having season ending shoulder surgery.

Clement was released after the 2007 season and has never pitched an inning since 2006.

No. 3. Edgar Renteria

Theo Epstein made the trade of a lifetime, a deal with the devil and has paid the consequences since.

Sending Boston icon, Nomar Garciaparra, to the Chicago Cubs in a three-way trade and receiving Orlando Cabrera, Epstein had firmed up a defensively weak position.

After winning the Series in 2004, Epstein let Cabrera walk and the shortstop carousel began.

In came Renteria.

Renteria was a complete flop for the Sox. He hit .277, second worst in his career, eight home runs and only stole nine bases.

If his hitting wasn't bad enough, Renteria's fielding was atrocious. He committed 30 errors, the most in his entire career and blamed Fenway's infield as his problem.

Theo saw enough and shipped Renteria to Atlanta for Andy Marte.

No. 2. J.D. Drew

After a dismal 2006 season, Epstein let Boston 'Dirt Dog', Trot Nixon, go and thought signing J.D. Drew to a $14M contract would be the answer.

He was wrong.

Drew suffered a miserable transition from the N.L. to the A.L.

Drew hit a career low 11 home runs. He also drove in 64 runs and only hit .270.

These were numbers Nixon would hit.

He would go one and hit what was called the '$14M Grand Slam' during Game 6 of the 2007 ALCS.

With David Ortiz out with a wrist injury, Drew came up clutch for the Sox in 2008, but, what hampered him though out his career, injuries took it's toll with Drew.

Drew is not known to be one to fight through injuries and is often referred to in Boston as 'Nancy Drew'.

So far in 2009, Drew is off to another slow start, hitting .258.

No. 1. Julio Lugo

Julio Lugo has been Theo Epstein's 'binky' for years. Epstein saw speed and power from Lugo. Rumors swirled in 2005 that Manny Ramirez would be dealt to Tampa for Lugo, Aubrey Huff and others.

Epstein would finally get to cash in, sign Lugo in 2007 and hopefully solidify the shortstop position once and for all.

He missed big time.

Lugo has been a major disappointment in a Sox uniform. He hasn't been able to hit nor field.

The Boston shortstop hit a putrid .237 in 2007. Last season, Lugo hit .268 before a knee injury ended his season.

With the glove, Lugo committed 19 errors in 139 games in 2007 and 16 in only 82 games during the 2008 season. This season he's already committed four errors in 14 games and has cost games for the Sox with his defense.