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Examining the 10 Worst Baseball Contracts of the Decade

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There have been plenty of free agent signings that have left fans puzzled and confused. Here are the 10 worst contracts in baseball in the 2010s.

10. Jacoby Ellsbury: Seven years, $153 million

When the New York Yankees stole Ellsbury from the Red Sox back in 2014, fans thought that it was the beginning of a championship roster for the pinstripes. They were severely mistaken. Injuries have ruined the outfielder’s New York tenure. He only made 111 and 112 appearances in 2015 and 2017, respectively, and was kept off the diamond entirely in 2018 and 2019. New York recently cut ties with the former Gold Glove outfielder but the club is currently in a battle over the remaining $26 million owed to him.

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9. Pablo Sandoval: Five years, $95 million

Sandoval was released in early 2018, and the only numbers that went up was his weight during his tenure with the Red Sox. He will make $5 million from the club this season to play for the Giants due to his retained salary. What did the Red Sox get out of him? Essentially one season’s worth of games (as he missed nearly the entire 2016 season), a .237/.286/.360 slash line, 14 home runs, and a WAR of -2.0, which means he was worth two wins fewer than a random, hypothetical, league average (and cheap) replacement would have provided. And, because of Sandoval, the Red Sox traded Travis Shaw after the 2016 season, only to watch him become a star for the Milwaukee Brewers.

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8. Josh Hamilton: Five years, $125 million

This one is hard to write about considering everything that surrounded Josh Hamilton. His contract with the Angels of $125 million over a five-year span was risky considering his history with drug addiction. At times, Hamilton looked like he was worth the risk, but those moments were in the minority. Injuries and a relapse with addiction led to his early retirement.

7. Matt Cain: Six years, $112.5 million

Cain rewarded the team with a perfect game (the 22nd in major league history) during the 2012 season, his best in the majors, but it was all downhill from there. After going 8-10 with a 4.00 ERA in 30 starts in 2013, the three-time All-Star was hampered by injuries and inconsistency. His 2017 year was a “comeback” of sorts as he started over 20 games for the first time since 2013 (23), but his numbers were among the most dismal. He went 3-11 with a 5.43 ERA and career-worst 1.657 WHIP and promptly retired.

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6. Jose Reyes: Six years, $106 million 

In 2012, the Marlins overpaid for the infielder. In those six years, Reyes was traded to Toronto after a lone great season with the Marlins in 2012 and the Blue Jays were so unimpressed with his lack of defense they flipped him to Colorado at the 2015 deadline for Troy Tulowitzki. He was neither very good nor very bad. After a suspension and 47 games with the Rockies, he was bought out and designated for assignment before latching back on with the Mets. They paid him the league minimum for parts of two seasons when he hit .246 in 2017 and just .189 in 2018. He became a free agent and another job in the majors has not appeared since.

5. Albert Pujols: 10 years, $240 million

This is not slander towards the future first-ballot Hall of Famer, but this contract itself was horrible. He recently joined the 3,000 hit club (which earned him an extra $3 million) and is sixth on the all-time home run leaderboard with 646 career dingers. If he actually plays out his contract, he could get into the top five by passing the likes of Willie Mays (660) and Alex Rodriguez (686). The problem is that Pujols signed an obscenely large contract with the Angels back in December 2011 — a ten-year, $240 million deal that will pay him until he is 41 years old. The contract was backloaded, meaning he actually gets paid more as he ages, which also comes with a decline in production.

4. Ryan Howard: Five years, $125 million

Ryan Howard quietly slipped away from baseball in 2016, hitting a horrible .196 with 25 homers just four years removed from signing a lucrative five-year, $125 million deal with the Phillies prior to the 2012 season. If it wasn’t injuries, it was poor production that made the former All-Star and deemed-best first baseman disappear.

3. Prince Fielder: Nine years, $214 million

When the Tigers signed Fielder to this massive deal, he was in his prime.With 228 homers in six seasons, he looked the part of an unstoppable force at the plate. Then, he had a .071 batting average in a World Series sweep at the hands of the San Francisco Giants in 2012, only to follow that up with an equally dismal turnout in the 2013 playoffs, when he hit .182 in the ALCS against Boston with no homers and no RBI. Fielder faded in the worst possible way and was dealt immediately following the season as the Tigers ate $30 million in salary. Fielder faded in Texas, with his 2015 All-Star season being the lone bright spot. As for his lone postseason appearance with Texas, the 2015 ALDS against Toronto, he hit .150 with one RBI. He hit just .212 in 89 games in 2016 and was forced to quit baseball due to serious neck injuries. He didn’t officially retire, though, as by not doing so he can collect the rest of that cushy deal until the end of 2020.

2. Carl Crawford: Seven yearss, $142 million

Crawford never hit his stride in Boston, as the former Devil Ray never played like he used to, only to complain and even grow a hatred for the franchise and its fanbase. He was subsequently traded to the Dodgers and added fuel to an unhappy chorus about his play by calling Boston fans “toxic.” He enjoyed a bit of a renaissance with the Dodgers in 2013 and 2014, but the injury bug bit again and his numbers declined precipitously in the last two seasons of his career, which ended after just 30 games (.185 batting average) in 2016. He still got paid, though.

1. Alex Rodriguez: 10 years, $275 million

A-Rod took a lot of grief for bad years in 2011 and 2012, hitting just 34 total homers between the two years and playing just 44 games in 2013 before being punished severely by MLB for his steroid use and missing a whole season via suspension. The 33-homer campaign of 2015 was a one-off, especially after he hit .200 in 65 games during the 2016 season with nine homers. He didn’t get quite the self-congratulatory retirement tour he probably envisioned as he slowly phased out in the waning months of 2016. Of course, he still got paid to the bitter end.

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