MLB is the only league in the Big Four that doesn’t have a salary cap—and as a result, it has one of the most aggressive free-agent markets out there.
This has led to quite a few big-name players getting signed to enormous deals that they can’t even come close to living up to.
Let’s take a look at the 10 worst free agent signings the league has ever seen.
Barry Zito – Giants
It isn’t entirely clear who the Giants were bidding against when they gave Barry Zito a seven-year, $126 million contract ahead of the 2007 season. After all, he was coming off the worst season of his career and was five years removed from winning his Cy Young.
Things quickly went from bad to worse for Zito, who never pitched to an ERA below four for the Giants.
Albert Pujols – Angels
The St. Louis Cardinals shocked everyone when they let their longtime slugger and surefire future Hall of Famer walk after the 2011 season.
Pujols packed his back and went out west to join the Angels on a ten-year, $250 million deal. He had a couple of decent years at the beginning of the contract, but by 2013, his average started floating around .250 and his power had all but deteriorated entirely.
To make matters worse for the Angels, he played out the entire deal all the way through his age-42 season, at which point he was absurdly overpaid considering his production.
Mo Vaughn – Angels
The Angels clearly didn’t deploy the eye test when signing a 30-year-old Mo Vaughn to a six-year, $80 million contract in 1998. Plain and simple, the man didn’t look built to last.
And he wasn’t. He played just two seasons in Anaheim before they shipped him off to the Mets, where he continued to under-perform.
Alfonso Soriano – Cubs
Alfonso Soriano was a stud during his lone season in Washington, 2006, and thus masterfully executed his contract year by going for 46 home runs and 41 stolen bases.
The Cubs bought it hook, line, and sinker, and signed the 31-year-old to an eight-year $136 million contract—a deal that Soriano never came close to earning.
Jason Bay – Mets
Signing Jason Bay ahead of the 2010 season, was an absolutely horrendous move—even to the Mets’ standards. To say that he didn’t live up to his four-year, $66 million contract is the understatement of the century.
Bay went from slugging 36 homers in ’09 for the Red Sox to six in 2010—and totaled just 39 across all four seasons he played in New York, before the Mets mercifully bought out the last year of his deal.
Gary Matthews Jr. – Angels
Gary Matthews Jr. was an All-Star exactly one time in his career—and it was during his age-31 season when he hit .313 for the Rangers.
The Angels, for reasons unbeknownst to me, then thought it was a good idea to sign the journeyman outfielder to a five-year, $50 million contract, after which he never got above .252 and continued to deteriorate defensively.
Anthony Rendon – Angels
Anthony Rendon was a huge part of the Washington Nationals shocking 2019 World Series run and the Angels decided they had to have him. They ponied up $245 million over seven years, but Rendon never came close to earning his keep.
He’s still yet to play more than 54 games in a season for the Angels and his production has plummeted well below league averages.
Jacob Ellsbury – Yankees
After dealing with Jacob Ellsbury as a member of the Red Sox for several years, the Yankees decided to try and lure Boston’s beloved outfielder to the dark side with a massive seven-year, $153 million contract.
It felt like an overpay right off the bat—and that was confirmed year after year, as Ellsbury struggled to live up to the expectations from his time in Boston. He really had just one decent season, then it got so bad that the Yankees attempted to void the end of his deal, citing his visit to an unapproved doctor.
Pablo Sandoval – Red Sox
Few MLB players have fallen off a cliff in the way that Pablo Sandoval has. One second, he is a Word Series hero for the Giants and widely considered one of the top third basemen in the game, the next, he is designated for assignment by the Red Sox three games into his second year of a five-year $95 million deal.
Carl Crawford – Red Sox
During his heyday in Tampa Bay, Carl Crawford was one of the most exciting baseball players to watch. He regularly led the league in triples and stolen bases and leading up to the fateful 2010 free agency period, he had his best season to date, posting a 7.0 WAR.
Crawford parlayed that performance into a seven-year $142 million deal with the Red Sox, but unfortunately, the good times came to a screeching halt there. His batting average plummeted from .307 to .255 and his stolen bases tumbled from 47 to 18 during his first season in Boston. All in all, he looked like a shell of himself, and Boston shipped him out of town 31 games into the second year of his deal.
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