The worst free-agent signings in baseball the last 10 years

Major League Baseball free agency is not without its risks. The next franchise-altering player can be sitting on the market, waiting to lead your team to glory. The same can be said about the next franchise-killing player.

That’s not to say teams shouldn’t get involved in the process. There are also plenty of times a key free-agent came through and helped lead their team to glory. Just ask Chicago Cubs fans how they feel about Ben Zobrist. Without him, the team may not have broken the curse.

MLB owners and general managers should probably take note of that this winter. Bad contracts can hurt a franchise temporarily, but a World Series win is priceless.

But let’s face it, it’s a lot more fun to focus on the bad deals. We went through each signing from the past 10 offseasons and singled out the worst one from that year. We’ll start with 2008 and make our way to last winter.

Ready? let’s do it:

Carlos Silva struggled after signing a deal worth almost $50 million. (AP Photo/Elaine Thompson)

Carlos Silva signs a four-year, $48 million deal with the Seattle Mariners
It was fair to question the Seattle Mariners’ bet on Carlos Silva almost immediately. In his four previous seasons with the Minnesota Twins, Silva was almost the definition of average. He compiled a 4.42 ERA with the club, which was good for a 102 ERA+, meaning he was only two percent better than the league average. To make matters worse, Silva had one of the worst strikeout rates in the league before signing his deal.

Silva posted an awful 6.81 ERA over two years with the Mariners before he was involved in a bad contract swap with the Cubs for Milton Bradley. He was exactly league-average during his one season in Chicago. The team cut him the following year, deciding it was better to pay him $11.5 million than keep him on the team for another season.
Runner-up: Aaron Rowand’s five-year, $60 million deal with the San Francisco Giants.

Oliver Perez signs a three-year, $36 million deal with the New York Mets
It’s pretty incredulous to think a deal under $40 million could have been the worst of the offseason, but here we are. There were other contenders, but Perez had the worst performance of the bunch. In just two years with New York, he posted a 6.81 ERA over 112 1/3 innings. He was released a year early and did not appear in the majors in 2011. To his credit, Perez worked his way back to the majors as an effective left-handed reliever after some time away.
Runner-up: Milton Bradley’s three-year, $30 million deal with the Cubs.

Chone Figgins signs a four-year, $36 million deal with the Mariners
There were few reasons to expect Chone Figgins to completely collapse after joining the Mariners. He was coming off an All-Star season, in which he hit .298/.395/.393 and finished 10th in the MVP voting. He looked like the ideal leadoff candidate: A speedy, high-contact player who relentlessly worked the count against pitchers and gave you excellent defense.

All of that came crashing down when he signed with Seattle. He still made solid contact, but it didn’t lead to the same success. His batting average plummeted, and pitchers started pounding the zone once they realized he couldn’t produce, leading to a diminished walk rate. Perhaps inexplicably, he completely lost his value on defense. He hit just .227/.302/.283 in three years with the team and was released before his contract ended.
Runner-up: Jason Bay’s four-year, $66 million deal with the Mets.

Carl Crawford declined mightily after joining Boston. (AP Photo/Winslow Townson)

Carl Crawford signs a seven-year, $142 million deal with the Boston Red Sox
In seven seasons before joining the Red Sox, Carl Crawford was a monster for the Tampa Bay Rays. He averaged .301/.344/.461 at the plate, while adding strong speed and great defense. He was coming off his fourth All-Star appearance in seven years and had just turned in his first top-10 MVP finish.

His performance took a turn upon joining Boston. Crawford posted an on-base percentage under .300 for the first time since his rookie season in 2011. He then spent most of 2012 injured before he was shipped to the Los Angeles Dodgers in a clear salary dump. Crawford briefly regained some of his value with the Dodgers initially, but injuries struck toward the end of that contract. Los Angeles cut him in June of 2016 with $35 million still on his deal.
Runner-up: Adam Dunn’s four-year, $56 million deal with the Chicago White Sox.

Albert Pujols signs a 10-year, $240 million deal with the Los Angeles Angels
Albert Pujols has been a productive player at times during his tenure with the Los Angeles Angels, but it’s tough to say he’s been worth that massive deal. Consider this: With St. Louis, Pujols hit .328/.420/.617, and averaged 40 home runs, over 11 seasons. With the Angels, he’s hit .262/.319/.459, and averaged 28 home runs. And he still has four years to go. Pujols is set to average $28.5 million until 2021. He’ll turn 38 before next season.

There’s a valid argument to be made for Prince Fielder, but it’s tough to blame him for the neck injury that forced his retirement. Not only that, but Fielder wasn’t as bad as you might remember after signing a nine-year, $214 million deal with the Detroit Tigers. He made the All-Star team three out of five seasons after inking the contract. Fielder’s deal was also insured, so the Texas Rangers aren’t paying full price on it after picking up Fielder in a trade.
Runner-up: Prince Fielder’s nine-year, $214 million deal with the Detroit Tigers.

Josh Hamilton’s free-swinging ways came back to bite him with the Angels. (AP Photo)

Josh Hamilton signs a five-year, $125 million deal with the Angels
There were signs Josh Hamilton was on the decline with he signed his massive deal with the Los Angeles Angels. Always a free swinger, Hamilton started chasing pitches out of the zone at an alarming frequency in 2012. That trend continued in 2013, and pitchers took advantage. Hamilton hit just .255/.316/.426 in two seasons with the Angels. He was traded back to the Rangers, but only played 50 games with the team in 2015. He spent the final two years of his deal trying to work his way back from various injuries.
Runner-up: Edwin Jackson’s four-year, $52 million deal with the Cubs.

Jacoby Ellsbury signs a seven-year, $153 million deal with the New York Yankees
It seemed like Jacoby Ellsbury was being paid for his breakout 2011, in which he smashed 32 home runs. Ellsbury failed to retain that power, but did turn in yet another solid year before the Yankees swooped in with their huge offer.

Since signing that deal, Ellsbury has hit .264/.330/.386 in four years with New York. He’s still owed $68.5 million, and the Yankees are reportedly willing to pay half of that to send him to another team.
Runner-up: Ubaldo Jimenez’s four-year, $50 million deal with the Baltimore Orioles.

Pablo Sandoval signs a five-year, $95 million deal with the Red Sox
Things fell apart the moment Pablo Sandoval left the Giants. The third baseman hit just .245/.292/.366 his first year in Boston, and spent his second year injured. Sandoval’s struggles led to even more focus on his weight during the offseason … to the point where his conditioning has become an annual spring training story. After slumping in 2017, Sandoval was released two-and-a-half years before his contract was up. He attempted to regain his stroke with the Giants, but failed to produce in his return.
Runner-up: James Shields’ four-year, $75 million deal with the San Diego Padres.

Chris Davis’ struggles with contact have limited his upside the past two seasons. (AP Photo/Gail Burton)

Chris Davis signs a seven-year, $161 million deal with the Baltimore Orioles
This was a tough one, as Davis was coming off a monstrous season in which he mashed 47 home runs before hitting the market. Over his career, though, Davis’ performance has varied wildly. His approach may have something to do with that. Davis isn’t a high-contact hitter, so it’s tough for him to sustain a high batting average. If he’s off, he struggles to hit .220. But when he’s on, he’s one of the most feared hitters in the majors. The Orioles have been stuck with the down version of Davis the past two years. He’s hit just .218/.322/.443 since signing that deal.

You could make the argument for Jason Heyward, who signed an eight-year, $184 million deal with the Cubs. But Heyward still plays exceptional defense. That should give him value and longevity over Davis, who only really has his bat to keep him afloat.
Runner-up: Jason Heyward’s eight-year, $184 million deal with the Cubs.

Ian Desmond signs a five-year, $70 million deal with the Colorado Rockies
Ian Desmond’s deal with the Colorado Rockies didn’t make sense from the start. The team already had plenty of outfield talent, and using Desmond at first seemed foolish. Not only that, but some questioned the money, especially after Desmond was two years removed from a sub-.300 on-base percentage. In his first year in Colorado, he proved the skeptics right, hitting .274/.326/.375, with just seven home runs.

Desmond’s always been a streaky hitter, so there’s still a chance he can rebound. He’ll make $15 million annually over the next four seasons. While that’s not crushing like some of these other deals, it’s not great compared to what else was out there last winter.
Runner-up: Kendrys Morales’ three-year, $33 million deal with the Toronto Blue Jays.

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Chris Cwik is a writer for Yahoo Sports. Have a tip? Email him at or follow him on Twitter!