The Unlucky 13: Worst Free Agent Signings

by Paulie Knep
Love of Sports Correspondent

This week the Giants demoted Barry Zito to the bullpen, just a season and change into his 7-year, $126 million contract. Zito’s deal is one of the worst free agent signings in baseball history and his struggles bring to mind a number of other atrocious contracts.

There are a number of reasons why a free agent signing may turn out unsuccessful. A team may overrate a player or overestimate his market value. Sometimes players give less effort after securing the big money. Other times a contract seems reasonable when it’s signed but the player doesn’t produce as expected due to injuries.

This is a list of the thirteen worst free agent signings in baseball history.

13. Jason Giambi, New York Yankees - 7 years, $120 million

Giambi hit 41 home runs in each of his first two seasons in the Bronx, after signing with the Yankees in December 2001. Since then his body has become brittle and his average has plummeted. He’s a terrible first baseman, but the Yankees are forced to play him in the field because he doesn’t hit nearly as well when he is the DH.

12. Albert Belle, Baltimore - 5 years, $65 million

The Orioles made the combative slugger the highest paid player in baseball following the 1998 season. He was a disruptive presence in the clubhouse and had two mediocre seasons in Baltimore before retiring with a degenerative hip condition.

11. Carl Pavano, New York Yankees - 4 years, $40 million

Pavano appeared in 17 games for the Yankees in 2005, his first season in Pinstripes. He missed the entire 2006 season due to a series of bizarre injuries and after making just two starts in April 2007, underwent Tommy John surgery. He’s won a total of five games for the Yankees. That’s $8 million per win.

10. Greg Vaughn, Tampa Bay - 4 years, $33 million

The one-time fifty home run hitter was moderately productive for the Devil Rays in 2000, his first season with the team. Then his average dropped to .233 in 2001 and .163 in 2002. Tampa Bay released him after the 2002 season with one year remaining on his contract.

9. Russ Ortiz, Arizona - 4 years, $33 million

The Diamondbacks signed this hurler following the 2004 season. Ortiz went 1-14 from May 2005 - May 2006. After beginning the 2006 season 0-5 with a 7.54 ERA the Diamondbacks released him in June, with two-and-a-half years and $22 million remaining on his contract.

8. Kei Igawa, New York Yankees - 5 years, $20 million, plus $26 million bid

Between his contract and the fee paid to the Hanshin Tigers, the Yankees committed $9 million a year for Igawa’s services. He went 2-3 with a 6.25 ERA last season before being demoted to the minors, where he remains today, despite the struggles of the Yankees’ starting pitchers. He wasn’t even called up when Phillip Hughes was placed on the disabled list.

7. Jason Schmidt, Los Angeles Dodgers - 3 years, $47 million

When the Dodgers signed Schmidt in December 2006 he was a month shy of his 34th birthday, had a history of shoulder problems and his best years were behind him. He was limited to just 25 innings in 2007 before undergoing shoulder surgery and has yet to pitch this season.

6. Kevin Brown, Los Angeles Dodgers - 7 years, $105 million

The Dodgers made Kevin Brown baseball’s first $100 million man after the 1998 season. He was in his mid 30’s at the time and no other team was willing to offer him nearly that much money. Though he had a couple of great years for the Dodgers, the surly right-hander averaged just nine wins a season for the Dodgers and Yankees over the duration of the contract.

5. Mo Vaughn, Los Angeles Angels - 6 years, $80 million

Vaughn gave the Angels two productive seasons after they signed him in 1998, but he put on a lot of weight, which his knees couldn’t handle. He missed all of 2001 due to injury, then was traded to the Mets, where he struggled through two injury-plagued seasons before retiring.

4. Chan Ho Park, Texas - 5 years, $65 million

Following the 2001 season, the Rangers made the South Korea native one of the highest paid pitchers in baseball. Upon his arrival in Texas his velocity was down and he was beset by injuries. Park went 9-8 with a 5.75 in 2002 and 1-3 with a 7.58 ERA in 2003. The Rangers traded him to San Diego in 2005.

3. Mike Hampton, Colorado - 8 years, $121 million

In 2001, the Rockies severely overpaid a couple of average hurlers, Hampton and Denny Neagle (five years, $55 million). Hampton pitched two seasons for the Rockies compiling a 22-25 record, with a 5.78 ERA. He’s had just one productive season since signing the deal and hasn’t pitched since 2005.

2. Barry Zito, San Francisco - 7 years, $126 million

The Giants signed Zito to this enormous contract, despite indications that his career was on the decline. He’s lost at least 5 MPH on his fastball, which is now in the low 80’s, leaving no discrepancy between his fastball and curveball. Zito’s pitching coach, Dave Righetti said Zito will likely never throw 90 MPH again. 

1. Darren Dreifort, Los Angeles Dodgers - 5 years, $55 million

Dreifort had minimal success and a history of arm trouble when the Dodgers gave him a long-term contract before the 2001 season. He injured his arm during the first year of the deal and missed the next season and a half. Dreifort never threw more than 94 innings or won more than four games in a season during the life of the contract. 

Honorable Mentions

Juan Pierre - 5 years, $44 million with the Dodgers in 2006
Scott Rolen - 8 years, $90 million with the Cardinals in 2002
Kevin Appier - 4 years, $42 million with the Mets in 2000
Richie Sexson - 4 years, $50 million with the Mariners in 2004
Wilson Alvarez - 5 years, $35 million with the Devil Rays in 1997
Shawn Green - 6 years, $84 million with the Dodgers in 1999