On the Ball: MLB’s Worst Free Agent Signings of the Last 10 Years

December 11, 2014 Updated: April 24, 2016

I don’t see Jon Lester and his new $155 million deal ending up on this list in five years, but then again, few saw Barry Zito’s deal becoming an albatross back in 2006. But it happens nearly every offseason: Owners bid against each other, driving up the price, and eventually someone’s spending $50 million on Gary Matthews Jr.

Here are the worst of those signings over the last 10 years.

10. Albert Pujols, Los Angeles Angels: 10 years, $240 million, starting in 2012—Just when everyone was collectively gasping at how awful the 10-year deal with A-Rod was looking, the Angels decided they needed one of their own. Admittedly, it looked like the production in Pujols’s early years would even out the back end, but that’s not been the case. Pujols is still an above-average first baseman—though not an All-Star anymore—but there’s still seven years and $189 million left for the soon-to-be 35-year-old.

9. Gary Matthews Jr., Los Angeles Angels: 5 years, $50 million, starting in 2007—Matthews hit .313 with 19 home runs for Texas in 2006, in a season where he turned 32 years old. Unfortunately for the Angels, it would be the only high point of his career. After foolishly out-bidding everyone for his services, Matthews hit 18 home runs the following season, with a .252 average, but that was his best as an Angel. Two years and a measly 12 home runs later, they traded him to the Mets, eating $22.3 of the $23.4 million remaining.

8. Chone Figgins, Seattle Mariners: 4 years, $36 million, starting in 2010—While the Angels have several players on this list, they were wise not to re-up one of their own in Figgins. The speedster had a great 2009, hitting .295, drawing 101 walks, and stealing 42 bases for L.A. After the Mariners signed him away, Figgins hit a career-worst .259 in 2010 in 161 games before the real slump kicked in. Chone hit just .188 in 81 games the next season and topped that with a .181 clip in 66 games in 2012 before being released by the Mariners, who ate the remaining $8 million.

7. Andruw Jones, Los Angeles Dodgers: 2 years, $36.2 million, starting in 2008—The talented Jones was MVP runner-up in 2005, but by 2007 he had slumped to a .222 average, and the Braves let the 10-time Gold Glover test free agency as a 30-year-old. Two years actually seemed like a reasonable deal, but Jones, who reportedly showed up to spring training 20 pounds overweight, continued his sharp regression, hitting just .158 in 75 games in 2008, and was released after the season.

6. Carl Pavano, New York Yankees: 4 years, $39.95 million, starting in 2005—Most people forget that Pavano was a Yankee at one time—mainly because they rarely saw him in pinstripes. After going 18–8 with a 3.00 ERA for Florida in 2004, Pavano came to the Bronx and promptly sported a 4.77 ERA in 2005 while making just 17 starts. That was his high point as a Yankee. Various injuries, including to his elbow, limited Pavano to just nine starts combined over the final three seasons.

5. Jason Schmidt, Los Angeles Dodgers: 3 years, $47 million, starting in 2007—Here’s all you need to know about this deal: Schmidt made just 10 starts over the duration of this contract, going 3–6 with a 6.02 ERA. That averages out to one win per season. In hindsight, it’s easy to bash the Dodgers for paying him this much money despite his age (he was 34 at the beginning of 2007), but he had made at least 29 starts in each of the five previous seasons. Unfortunately a shoulder injury robbed him of any value Los Angeles could get from him.

4. Barry Zito, San Francisco Giants: 7 years, $126 million, starting in 2007—Zito had great credentials when he came to the Giants—a Cy Young Award and three All-Star nods—so it was quite a surprise when he struggled. Despite pitching in a pitcher’s park, Zito never put up an ERA below 4.00 in his seven years with the Giants and even led the league in losses (17) in 2008. Amazingly, the Giants won a pair of World Series titles in his time, and Zito actually contributed to the cause in 2012 when he was put on the playoff roster and garnered a pair of wins.

3. Jason Bay, New York Mets: 4 years, $66 million, starting in 2010—The good news for Mets fans is that this one is finally over. A puzzling collapse for sure, Bay was one of the more feared power hitters in the game with Pittsburgh and Boston—he hit 36 home runs the year before he signed with New York. But he hit just 26 total homers in three seasons for the Mets before being released. Injuries and a power-sapping home ballpark contributed to his demise.

2. Josh Hamilton, Los Angeles Angels: 5 years, $125 million, starting in 2013—Hamilton has hit .250 and .263 in his two seasons in California thus far—his two lowest batting averages of his career—this after five straight All-Star seasons and an MVP in his time with the Rangers. His power has disappeared as well, as he’s hit 31 home runs in 240 games. What makes this even worse for the Angels, though, is that the contract is heavily back-loaded. Hamilton, who turns 34 next May, is scheduled to make $25 million this year and then $32 in 2016 and 2017.

1. Alex Rodriguez, New York Yankees: 10 years, $275 million, starting in 2008—This was a head-scratcher from the day it was signed—the length of it, that is. A-Rod was coming off his third MVP in five seasons, but he was 32 years old. Who’s still worth $20 million a year into their 40s? This was also before the alleged PED use and subsequent suspension in 2014. The Yankees got in at the worst time, and they were only bidding against themselves.