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Top 10 Worst Baseball Contracts

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The toughest question for the general manager of any baseball team is whether to pull the trigger and offer a player coming off a big year a huge contract. No matter what fans think there’s no way to tell for sure if a player will continue at the top of his game after re-signing. The World Series features two teams, the Kansas City Royals and the San Francisco Giants, who eschewed off-season splurges and relied on smaller contracts and young, untested, players — particularly the Royals. 

For every Derek Jeter who plays well until the end of his career, there are tales of those who fall off the career cliff after hitting the big payday. Maybe it’s the pressure of the big contract. Sometimes injuries hamper performance.

Whatever the case, teams are left on the hook for big salaries that can’t be used to pay players who can produce. Few teams have the budget to overcome such a situation.

With that in mind we decided to look at the Top 10 Worst Baseball Contracts. There was no shortage of candidates. For instance, some would argue that Ryan Braun of the Milwaukee Brewers, who has been plagued by a long suspension and a bad thumb, should make the Top 10. And he’s not the only one we considered.

(To see other bad (and some good) contracts check out the Top 10 Best & Worst Baseball Contracts.)

Although there are plenty of bad contracts to mull over, one player from that earlier list managed to make this one. Click through to find out how we ranked the worst contracts and who managed to stay on our list.

Dan Uggla, second baseman for the Atlanta Braves. (Photo: AP)

10. Dan Uggla

Money: $39 million

Duration: 3 seasons (2012-2014)

Team on the Hook: Atlanta Braves

Uggla would be higher on our list but his salary of just $13 million per year for two seasons makes him somewhat of a bargain among the worst contracts. The second baseman never hit for a high average, but he had three seasons with more than 30 home runs and hit a career high .287 in 2010 for the Florida Marlins. His 36 homers in 2011 were enough for the Braves to sign him to a three-year deal (the team had acquired Uggla in a trade). A .179 average and 22 homers in 2012 were just the start of his woes at the plate. Uggla hit just .149 the following season and was cut this past season with his average at .162. Amazingly, the San Francisco Giants gave him a shot, but that lasted just four games and 12 plate appearances.

Mark Teixeira, first baseman for the NY Yankees . (Photo: AP)

9. Mark Teixeira

Money: $180 million

Duration: 8 years (2009-2017)

Team on the Hook: New York Yankees

The Gold Glove first baseman was riding high when he became a free agent. He had regularly hit more than 30 home runs and driven in more than 100 with the Texas Rangers, Atlanta Braves and Los Angeles Angels. His left-handed stroke seemed perfect for the reconstituted House that Ruth Built. His stint as the Yanks first baseman started out well, with three seasons of more than 30 homers and 100 RBI, though with a declining batting average. But injuries have taken their toll, along with teams employing a defensive shift, and Teixeira’s numbers have plummeted. He hit just .216 in 2014 with 22 homers. With three more seasons left on the deal, Yankee management and fans can only hope he gets things turned around.

Josh Hamilton, outfielder for the Los Angeles Angels. (Photo: AP)

8. Josh Hamilton

Money: $125 million

Duration: 5 years, (2013-2017)

Team on the Hook: Los Angeles Angels

Hamilton was touted as a can’t miss prospect with the Cincinnati Reds until a well-documented struggle with drug and alcohol addiction derailed his career. Overcoming those problems gave him a new chance with the Texas Rangers and he made the most it, parlaying it into a big contract with the Angels. Alas, his batting average has plummeted (.250 and .263 the last two seasons) and he has hit just 31 home runs total with the Halos. Injuries hampered him this season. Does he have another comeback in him?

Joe Mauer, catcher for the Minnesota Twins. (Photo: AP)

7. Joe Mauer

Money: $185 million

Duration: 8 years (2010-2017)

Team on the Hook: Minnesota Twins

Hometown boy makes good is such a time-honored cliché in the sports world. For the St. Paul, Minnesota, native the cliché came true as he rose to stardom as the Minnesota Twins catcher. And with success came a big contract meant to lock Mauer up for the rest of his career. As with many great plans, reality did not quite match the blueprint. Though he has hit well for the first three years of his new contract, Mauer has suffered a series of concussions that decreased his productivity in 2014. He was moved to the less stressful position of first base to try to extend his career.

B.J. Upton, outfielder for the Atlanta Braves. (Photo: AP)

6. B.J. Upton

Money: $75.25 million

Duration: 5 years (2013-2017)

Team on the Hook: Atlanta Braves

If it seemed like a dream, maybe that’s all it was. B.J. Upton starred for the Tampa Bay Rays, helping lead them to the 2008 World Series. Meanwhile, his brother Justin was enjoying success with the Atlanta Braves. They even managed to reach the 100 home run mark for their careers on the same day. Life became even sweeter when B.J. entered free agency and signed with the Braves. The dream though turned nightmarish. Although the brothers socked back-to-back homers early in the season, B.J.’s first season with the Braves was awful. He batted just .184 with 26 RBI. His batting average for 2014 “bounced back” to .208.

Albert Pujols, infielder for the Los Angeles Angels. (Photo: AP)

5. Albert Pujols

Money: $240 million

Duration: 10 years, (2012-2021)

Team on the Hook: Los Angeles Angels

Albert Pujols was one of the few power hitters that escaped the steroid era without a whiff of scandal. When he got his turn at free agency, the St. Louis Cardinals offered him a handsome contract. Pujols, though a Cardinal his entire career, went for the dollars in Anaheim. After a horrid start, Pujols has played better for the Angels, but not enough to justify his big payday in the minds of many. Meanwhile, the Cardinals fans that were so upset when Pujols left have watched their team continue to be among the elite of the National League, and make it back to the World Series.

Carl Crawford, left fielder for the Los Angeles Dodgers. (Photo: AP)

4. Carl Crawford

Money: $142 million

Duration: 7 years (2011-2017)

Team on the Hook: Boston Red Sox & Los Angeles Dodgers

It’s hard to say which team was more reckless, the Boston Red Sox for granting the gargantuan contract to Crawford, or the Dodgers for assuming the last five years and $100 million of the deal. In two seasons with the Dodgers, Crawford has managed to hit just 14 homers and drive in 77 base runners. The Red Sox, meanwhile, won the World Series last year. The free-spending Dodgers, meanwhile, have fallen short of winning the title the last two seasons.

Prince Fielder, infielder for the Texas Rangers. (Photo: AP)

3. Prince Fielder

Money: $214 million

Duration: 9 years (2012-2020)

Team on the Hook: Detroit Tigers & Texas Rangers

Fielder was truly the big man on his team. Less than 6 feet tall and wide of body, Fielder packed a wallop. He helped lead the Milwaukee Brewers back to the playoffs after nearly a quarter-century of futility. Then, following the money, he ended up in Detroit, joining the same Tigers that his power-hitting father, Cecil, had played for in the 1980s. The Brewers haven’t been the same since he left, but two horrible postseasons spurred the Tigers to send Fielder packing. He was traded to Texas where he missed much of this past season with a neck injury. Time will tell if his best seasons are behind him.

Ryan Howard, Infielder for the Philadelphia Phillies. (Photo: AP)

2. Ryan Howard

Money: $125 million

Duration: 5 years (2012-2016)

Team on the Hook: Philadelphia Phillies

The Phillies have had a long history. Losing has marked most of it. Howard was the key power hitter in a lineup that helped propel the team to a World Series win in 2008. For his home runs and excellent play at first base, Howard reaped the rewards. Then disaster struck in the form of a torn Achilles tendon on the last play of the 2011 National League Championship series. Howard made the last out of the game and crumpled to the ground before he reached first. He hasn’t been the same player since. After struggling for two seasons in which he produced 25 total home runs, he bounced back a little in 2014 with 23 to go with 95 RBI. That’s a far cry from the feared slugger the Phillies thought they had signed for five years.

Alex Rodriguez, third baseman for the NY Yankees. (Photo: AP)

1. Alex Rodriguez

Money: $275 million

Duration: 10 years (2008-2017)

Team on the Hook: New York Yankees

A-Rod is the man who was on our previous list of baseball contracts in 2011. He actually was cited for two contracts then, one deemed good and one not so great. Rodriguez has set the gold standard for achievement throughout his career. First, as a teenager he quickly became a superstar by belting home runs and playing a superb shortstop for the Seattle Mariners. Then it was on to Texas, where the Rangers made him the highest paid player the sport had seen. Then the Yankees rewarded him with the biggest contract ever. The contract started out well with A-Rod having three stellar seasons, but injuries and a season-long suspension for PEDs made it even worse. The Yankees are in luck though as they think about next season: he’s baaaaaaaaack.

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