10 of the Worst Baseball Contracts Ever

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Sometimes the best course of action is to do nothing. This is doubly true when the time comes to offer large sums of guaranteed money over the course of several years to players who might, or might not, deserve it. Sometimes these terrible decisions are the fault of no one. Injuries can play a large factor in a player’s career. Then again, some decisions are so egregious that they cannot be forgiven. For one reason or another, here are ten of the worst baseball contracts ever signed.

10. Mo Vaughn - Anaheim Angels (1999) - 6 Years, $80 Million

At the time, this didn’t seem like a terrible deal. Vaughn just mashed pitchers. In the six previous years he averaged 36 home runs and 110 RBIs while maintaining a .315 batting average. He was a premier offensive player and the Angels were absolutely thrilled to sign the 31-year-old. His first two years weren’t terrible, but injuries and excess weight took their toll. Vaughn was eventually traded to the Mets, and while he continued to hit home runs he never really regained his pre-contract form.

9. Russ Ortiz - Arizona Diamondbacks (2005) - 4 Years, $33 Million

Russ Ortiz should have been worth the money the Diamondbacks threw at him. Leading up to 2005 he’d won at least 14 games in six consecutive seasons. He had years where he won 17, 18 and 21 games and his ERA was routinely under 3.85. Arizona jumped at the opportunity to add Ortiz to their staff – and no one could blame them. Ortiz won five games for the Diamondbacks, total. He missed several months with an injury and was never ever the same. The start of his 2006 season was so bad that the D-backs actually cut Ortiz with two and a half years and $22 million left on his contract! At the time it was the largest buy-out in major league baseball history.

8. Denny Neagle - Colorado Rockies (2001) - 5 Years, $51.5 Million

Denny Neagle was a ground ball pitcher heading to a team in desperate need of keeping the ball on the ground. He’d been effective for other teams and finished third in the National League Cy Young voting in 1997 while pitching for Atlanta. Neagle seemed less than bothered by the number of home runs hit at Coors Field. He was in for a shock. His 31 starts netted him a 10-10 record and a 5.77 ERA. Amazingly, he wasn’t any better outside of Colorado, going 9-13 and posting an obscene 5.36 ERA. In an odd twist of fate the Rockies caught a bit of a break when Neagle was arrested for soliciting a prostitute, which allowed the club to void the final year of his contract.

7. Darren Dreifort - Los Angeles Dodgers (2001) - 5 Years, $55 Million

For the majority of his career, Dreifort was a serviceable pitcher. He posted decent numbers, but nothing to get overly excited about. In seven years with the Dodgers, Dreifort won 39 games and lost 45. His 4.38 ERA and 1.38 WHIP were average, at best. Then, at the tail end of the 2000 season, Dreifort went on a tear. He finished the last three months of the season with an 8-2 record, a 3.43 ERA and 96 strikeouts in just over 99 innings pitched. That prompted the Dodgers to sign the 32-year-old to a five-year, $55 million deal that never quite worked out for anyone. Dreifort only started 10 more games for the Dodgers and battled a constant stream of injuries before being converted to a reliever. Even that didn’t work. Dreifort retired, largely because of injuries, in 2005.

6. Kei Igawa - New York Yankees (2007) - 5 Years, $46 Million

This contract is a bit deceiving since it includes the $26 million posting fee the Yankees paid just to negotiate with Igawa. Even if you remove that fee it’s still a bad deal. Igawa played in a total of 16 professional games, starting 14 in 2007 and another two in 2008. His numbers were abysmal. His career ERA is 6.66 and his WHIP 1.75. The Yankees buried Igawa in AAA, where he was surprisingly solid. He finished his career well-paid, but never again pitched in the major leagues.

5. Barry Zito - San Francisco Giants (2006) - 7 Years, $121 Million

Barry Zito earned every right to negotiate this massive contract. He was far and away the best free agent pitcher heading into the 2007 season. He’d won a Cy Young Award and 102 games with the Athletics. His demands? Only the richest contract in baseball history. Amidst the chaos emerged the Giants, who ponied up the money with the expectation that they’d be getting a front-line starter for the better part of a decade. Zito won 15 games while posting a 4.15 ERA in 2012, marking it the only season he’d posted a winning record since joining the Giants. To say Zito has been average since signing the contract is an understatement. He hasn’t posted an ERA under 4.00 yet. He’s received something of a pass since the Giants have managed to win two World Series since he joined them, but Zito has never fully lived up to what the Giants expected when they signed him.

4. Mike Hampton - Colorado Rockies (2001) - 8 years, $121 Million

At the time, this was the largest contract in baseball. Mike Hampton spent the previous six seasons pitching in Houston and New York where he racked up 84 wins, including 22 in 1999 when he finished second in Cy Young voting. He was the best pitcher available at the time and his repertoire of sinkers, cutters and other ground-ball-inducing pitches were thought to be a commodity in the lighter Colorado air. Hampton pitched for the Rockies for two years, posting a 21-28 record. His walk rate, ERA and WHIP were awful. He was traded twice during the 2003 off-season, and while he had a couple decent seasons, injuries and ineffectiveness on the mound ensured he'd never fulfill the expectations of his mammoth contract.

3. Carlos Silva - Seattle Mariners (2008) - 4 Years, $48 Million

Silva was an average ground ball pitcher who played with one of the best infield defenses in the mid-2000s. Even so, he wasn’t all that good to begin with. Silva gave up a league-leading 38 home runs in 2006. He also walked a lot of batters. That didn’t stop the Mariners from offering him an obnoxious four-year deal that Silva would have been insane to pass up. Needless to say, it didn’t work out well. Silva’s best year in Seattle was his first, when he went 4-15 with a 6.46 ERA. Yes, that was his best year. The following season, he was 1-3 with an 8.60 ERA and only appeared in 8 games. Silva was traded to the Cubs the following year where he put numbers which better matched his career marks.

2. Jason Schmidt - Los Angeles Dodgers (2007) - 3 Years, $46 Million

Like others before him, Jason Schmidt earned this deal. He was stellar for the Giants, making three All-Star appearances and finishing in the top-five in Cy Young voting twice. He’d won 11 or more games in each of the previous five seasons and his ERA was more than respectable. Even though he was 34, the Dodgers plucked Schmidt off the free-agent market thinking they’d get a top-end starter. They were so wrong. Schmidt experienced numerous shoulder injuries which limited him to six starts in 2007. Those injuries cost him the entirety of the 2008 season and again limited him to four more starts in 2009. All told, the Dodgers ended up spending $46 million for 10 starts and a 6.02 ERA from Schmidt.

1. Alex Rodriguez - New York Yankees (2008) - 10 Years, $275 Million

Rodriguez actually opted out of his previous 10-year, $252 million deal to sign this one. At first glance it doesn’t look all that bad. Rodriguez posted some impressive numbers in the first three years of this deal. But A-Rod was 32 years old when this contract was inked and it was unreasonable to believe he’d continue to put up the gaudy numbers of his past. A-Rod’s stats began to decrease significantly in 2011, largely because of injuries. In fact, Rodriguez hasn’t played in more than 138 games since singing this deal. He constantly battled a wide variety of injuries and of course, there’s his implication in a PED scandal which has put him out for the entire 2014 season. Although he's losing $25 million this season, the Yankees are still obliged to fork over $5.9 million to him in salary and a signing bonus.