Ranking the Worst MLB Free-Agent Signings of the Last 10 Years

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Ranking the Worst MLB Free-Agent Signings of the Last 10 Years
Stephen Dunn/Getty Images
Hamilton is an early candidate for a future "Worst Contract of All Time" list.

Teams hoping to upgrade their roster via free agency each offseason have more than a few examples of why they should be cautious. Exhibit A would be Alex Rodriguez and his ten-year, $275 million contract, which doesn’t expire until after the 2017 season. Rodriguez will be 42 years old, and his best days are far behind him. 

If this past offseason was any indication, teams will be trying to stay away from these types of long-term deals that will pay players well past their prime. Only seven free agents signed deals for longer than three years, and only one, Josh Hamilton, will be over 35 years of age at the end of the contract. 

Zack Greinke will be 34 years old when his six-year deal with the Dodgers expires. Angel Pagan will be 35 when his contract in San Francisco runs out. The Indians’ big free-agent signings—Michael Bourn and Nick Swisher—could become free agents at ages 33 and 34 respectively. Edwin Jackson of the Cubs and Anibal Sanchez of the Tigers will both be 33 when they can become free agents again. 

The Angels’ signing of 31-year-old Josh Hamilton to a deal with less than half the financial commitment (five-year, $133 million) of Rodriguez’s was still considered a huge risk because of his prior off-the-field issues. It’s his early season performance, however, that should have the Angels worried. 

Through his first 20 games, Hamilton is hitting .221 (17-for-77) with two homers, five walks and 23 strikeouts. The five-time All-Star also looked bad at the end of last season. 

While it’s not the first time a superstar player has struggled out of the gate, it should be noted that Hamilton’s career numbers at Angel Stadium, where he’ll play half of his games, are just average (.779 OPS). The same goes with Oakland Coliseum (.751 OPS.) and Safeco Field (.746 OPS), home stadiums of division rivals A’s and Mariners. 

For the next five years, Hamilton will play more than 60 games less per season at Rangers Ballpark in Arlington, where he has a career .961 OPS. Even if he’s still the same player and his skills haven’t declined, he might not come close to the numbers he had with Texas. 

This time last year, the Angels were worried about the guy they had just signed to a ten-year, $240 million deal. Albert Pujols being “done” with ten years left on his deal probably would’ve put him at the top of the “Worst Free-Agent Signing Ever” list. 

Fortunately for the Angels, he showed he had plenty left in the tank with a strong finish after posting a .506 OPS through his first 27 games. The 33-year-old has an .803 OPS through 19 games this season, although he’s playing with plantar fasciitis and could eventually land on the disabled list because of the ailment.   

Pujols will be 41 during the last year of his deal, and as is the case with Rodriguez, there are plenty of valid concerns regarding his health and declining skills as he approaches his mid-30s. He’ll have eight years and $211 million remaining on his deal after this season.  

Along with Hamilton, it wouldn’t be a huge surprise to see Pujols on a similar “Worst Free Agents” list a few years from now. In case you needed a refresher on Rodriguez and some other bad contracts, here’s my top 10 from the past decade.

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