Top 5 Worst MLB Contracts of All-Time
With the unsurprising news on Wednesday that the LA Angels' $245 million man Anthony Rendon will be out "long-term", we present to you the Top 5 Worst MLB Contracts of All-Time.
1. Anthony Rendon, LA Angels, 7 years, $245M
Yes, Rendon has completely robbed the Angels blind over the past five years, and today's announcement of hip surgery and another lost season could be the last anyone ever sees of Rendon on a baseball field.
He has missed 451 of 708 potential games since signing that albatross of a contract before the 2020 season. If he misses the entire 2025 season (and why wouldn't he?), he'll have missed a full 70% of his team's games in his six years in Anaheim. By then, his 22 total home runs for the $207M in salary he'd have collected at that point will work out to $9.4M per HR in an Angels uniform.
What makes his horrendous first five years under this contract even worse, is that he's never seemed to care one iota that he let the organization, or the fans, down.
I used to be a big Rendon guy. But he has zero ability to stay on the field, and what's worse is he doesn't give a shit as baseball is 100% just a job to him. Stealing money for 6 seasons now and he doesn't care if he ever plays another inning. Screw this guy. https://t.co/asBCZFngPX
— Paul Valle III (@PaulValleIII) February 12, 2025
2. Stephen Strasburg, Washington Nationals, 7 years, $245M
After winning the World Series (with Rendon) in 2019, the Nats rewarded their injury-prone starter Strasburg with this massive deal, but they had no idea at the time of the magnitude of his injury issues. He would only ever start 8 more games—with 1 victory—over the course of the next three seasons before his career was over. That one win in the middle of May, 2021, was one expensive victory.
3. Chris Davis, Baltimore Orioles, 7 years, $161M
Davis was the game's pre-eminent slugger in the winter of 2015, after mashing 126 home runs in the three previous seasons alone. The Orioles rewarded him with this insane deal, and watched as he disintegrated before their eyes, year after year, watching his HR totals go from 38 to 26 to 16 to 12 to 0, and his batting average plummet year over year all the way down to .115 in his final season in 2020, and he never appeared in the majors again.
4. Pablo Sandoval, Boston Red Sox, 5 years, $95M
Panda went from a cuddly, clutch hitter for the San Francisco Giants, averaging .285 over 11 seasons with them, and an OPS just a tick under .800. After he signed his huge deal with the Red Sox in 2015, he showed up to spring training grossly out of shape, and his average proceeded to drop 50 points to just .237 in three years in Boston, while his OPS plummeted 150 points to .646 over that time. He managed to play just 161 games over a three-year period. They finally DFA'd him, and he wound up back in San Francisco, where he found a bit of his game, leaving even more humiliation for the Red Sox.
5. Josh Hamilton, LA Angels, 5 years, $125M
Who could forget the infamous Josh Hamilton deal? Certainly not Angels fans, who find themselves on this list twice. Hamilton was a 5-time All-Star with the Texas Rangers, mashing 150 HR over that period. After he signed with the Angels in 2013, injury problems and repeated drug & alcohol relapses completely derailed his career and he managed just 39 homers over three years until his career came crashing to an end.
Bonus: 6. Chris Sale, Boston Red Sox, 5 years, $145M
Suffering a series of injuries that team head honcho Chaim Bloom would call "an incredibly bizarre run of events," Sale would pitch in just 11 games in his first three seasons after signing this massive extension in 2020, and finally, after starting 20 games in 2023, he was dealt away to the Atlanta Braves, having won 11 games total over the course of that contract.
Of course, to add to the Red Sox' embarrassment once again, Sale went on to win the Cy Young award in his first season last year with the Braves.
Photo: © Frank Becerra Jr / USA TODAY NETWORK
