MLB's Worst Free-Agent Deals
With big money comes big expectations. Plenty of baseball players have had to face that harsh reality over the years. Detractors often shout "overpaid" before big-money contracts even get finalized.
This sentiment is not without merit. Many big-money signings have failed to live up to their contracts. Some have crumbled entirely under the pressure of a new market, big money or both.
These players delivered little return on investment. Now, they are major league cautionary tales for teams looking to make a free-agent splash.
Note: Stats for active players are through April 9, 2019.
30. Edgar Renteria — Boston Red Sox
Contract: Four years, $40 million
Return on investment: 153 games played, .276 BA, .721 OPS, 8 HR, 172 hits, 1.4 WAR
Bottom line: Shortstop was a revolving door for the Boston Red Sox in the mid-2000s, despite their success. By signing veteran Edgar Renteria, they hoped to close the turnstile. It didn't work out.
His one year in Boston was a disaster in the field, where he had been a reliable defender. He committed a career-high 30 errors and had a career-low .954 fielding percentage with the Red Sox.
In the 2005 offseason, Renteria was traded to the Atlanta Braves for cash and Andy Marte.
29. A.J. Burnett — New York Yankees
Contract: Five years, $82 million
Return on investment: 98 games started, 34-35 W-L, 4.79 ERA, 584 IP, 513 Ks, 3.7 WAR
Bottom line: There’s no denying his talent. A.J. Burnett was a stud for the Marlins and Blue Jays prior to inking a big contract with the Yankees.
He was affected by the bright lights of New York, as his ERA soared to above a 5.00 in two of his three seasons, until the Yankees sent him to Pittsburgh, where he was a solid started once again.
28. Carl Pavano — New York Yankees
Contract: Four years, $39.9 million
Return on investment: 26 games started, 9-8 W-L, 5.00 ERA, 145 IP, 75 Ks, 0.4 WAR
Bottom line: By Yankees standards, the dollar figure isn’t too lofty, but the production still fell well short of expectations.
Carl Pavano was a curious signing to begin with, having posted just one All-Star season before joining the Bronx Bombers, and his three years as a Yankee were filled with injuries and lots of home runs.
27. Esteban Loaiza — Oakland A’s
Contract: Three years, $21.4 million
Return on investment: 28 games started, 12-9 W-L, 4.62 ERA, 169.1 IP, 102 Ks, 1.3 WAR
Bottom line: Esteban Loaiza joined a stellar A’s rotation in 2006 and was supposed to be a reliable fifth starter to solidify the corps for years to come. He was not that.
The right-hander posted a 4.89 ERA in his first year, and a dreadful 7.36 ERA in the playoffs.
Luckily for the A’s, the Dodgers grabbed him off waivers in 2007, getting Oakland off the hook for the remaining salary.
26. Heath Bell — Miami Marlins
Contract: Three years, $27 million
Return on investment: 73 games played, 4-5 W-L, 5.09 ERA, 63.2 IP, 19 SV, -0.4 WAR
Bottom line: Heath Bell was lights out with the Padres after taking over at closer for Trevor Hoffman. But Bell's numbers in Miami were brutal from the start.
He posted a 5.09 ERA in his first year before being traded to Arizona.
25. Darryl Strawberry — Los Angeles Dodgers
Contract: Five years, $20.25 million
Return on investment: 214 games played, .243 BA, .786 OPS, 38 HR, 185 hits, 2.9 WAR
Bottom line: Darryl Strawberry was an All-Star right fielder in his last seven season with the New York Mets and one of the game’s best young power hitters when the Los Angeles Dodgers locked him up to a high price for the time.
Drug issues no doubt affected his performance in Los Angeles, where the local legend out of Crenshaw High School fizzled out in his third season after another All-Star campaign in the first.
His Baseball Reference page tells the story of a man with all the tools who couldn’t keep it together.
24. Gary Matthews Jr. — Los Angeles Angels
Contract: Five years, $50 million
Return on investment: 370 games played, .248 BA, .708 OPS, 30 HR, 312 hits, 0.0 WAR
Bottom line: Regarded as a top-notch defensive center fielder, Gary Matthews Jr. was coming off his best offensive season as a Texas Ranger when the Angles inked him to big money.
He never approached that production level again and was shipped to the Mets for a relief pitcher three years later.
23. Yasmany Tomas — Arizona Diamondbacks
Contract: Six years, $68.5 million
Return on investment: 305 games played, .268 BA, .769 OPS, 48 HR, 295 hits, -2.4 WAR
Bottom line: The legacy of the short-lived Tony LaRussa regime in Arizona is to blame for this. Yasmany Tomas looked to be a good young player from Cuba, but few saw him commanding this price tag.
The detractors were correct, as Tomas has had one solid year as outfielder/third baseman bookended by two poor ones.
He is now back in the minors.
22. Mo Vaughn — Los Angeles Angels
Contract: Six years, $80 million
Return on investment: 300 games played, .276 BA, .865 OPS, 69 HR, 314 hits, 3.6 WAR
Bottom line: Mo Vaughn cashed in after years of bashing homers over the Green Monster in Boston by signing with the Angels following his third All-Star season with the Red Sox.
Injuries and personal care cost him years off his career and slowed his production in Anaheim.
He had two decent seasons at the plate, but missed one entirely due to injury and only lived out three of those six contracted years in the big leagues.
21. Nick Swisher — Cleveland Indians
Contract: Four years, $56 million
Return on investment: 272 games played, .228 BA, .688 OPS, 32 HR, 230 hits, 1.6 WAR
Bottom line: The Indians thought they got a steal when Nick Swisher signed with the club in 2013 after posting an OPS above .800 in six of his previous seven seasons.
Looks like Yankee Stadium may have inflated those numbers, and Swisher was dealt to the Atlanta Braves in the deal’s third year.
By 2016, he was out of baseball.
20. Ian Desmond — Colorado Rockies
Contract: Five years, $70 million
Return on investment: 266 games played, .246 BA, .705 OPS, 29 HR, 230 hits, -2.2 WAR
Bottom line: Maybe this is a bit premature, but two years into this deal, and the Rockies have severe buyer’s remorse.
Colorado has not lifted Desmond’s power number. In fact, Coors Field has done just the opposite, as his OPS hovers around .700.
With three years more to go, Desmond needs to a big rebound to make this move a good deal for the Rockies.
19. Milton Bradley — Chicago Cubs
Contract: Three years, $30 million
Return on investment: 124 games played, .257 BA, .775 OPS, 12 HR, 101 hits, 0.3 WAR
Bottom line: Milton Bradley was volatile player on and off the field, but there's no denying his talent.
Bradley had been an outstanding hitter for the Padres and Rangers before landing this deal with Chicago.
But he battled with the media and other teammates, which stifled his production and led to an exit after just one season.
18. Ian Kennedy — Kansas City Royals
Contract: Five years, $70 million
Return on investment: 85 games started, 19-33 W-L, 4.47 ERA, 473.1 IP, 422 Ks, 5.0 WAR
Bottom line: Ian Kennedy’s deal with the Royal puzzled plenty of analysts around the league. He had been a solid No. 3 or No. 4 starter in San Diego, with not a great upside.
Despite this reality, the Royals were desperate for pitching and locked down Kennedy, who has posted back-to-back dreadful seasons after a decent debut year in Kansas City.
17. Albert Pujols — Los Angeles Angels
Contract: 10 years, $254 million
Return on investment: 999 games played, .259 BA, .767 OPS, 189 HR, 1,018 hits, 13.2 WAR
Bottom line: It’s clear by the payday that the Angels expected to get the St. Louis version of Albert Pujols for at least a few more years. That is not what showed up to Anaheim.
Pujols has been a far less efficient and dynamic hitter — hitting for a lower average and far less power.
His contact rate is still good, and he is a threat to hit 30-40 homers, but he is a long way from his prime as a ballplayer.
16. Chan Ho Park — Texas Rangers
Contract: 5 years, $65 million
Return on investment: 68 games started, 22-23 W-L, 5.79 ERA, 380.2 IP, 280 Ks, 1.2 WAR
Bottom line: Chan Ho Park was an innings eater and overall stud for the Dodgers, making the All-Star team in his final year in Los Angeles, before heading to Texas.
He couldn’t take the heat. Maybe it was that, or maybe the expectations, as Park pitched poorly to start his tenure and was injured throughout.
He returned to Los Angeles a few years later and had a brief resurgence in his old stomping grounds.
15. Russ Ortiz — Arizona Diamondbacks
Contract: Four years, $33 million
Return on investment: 28 games started, 5-16 W-L, 7.00 ERA, 137.2 IP, 67 Ks, -2.2 WAR
Bottom line: Russ Ortiz appeared poised to enjoy a long career as an innings eater after stints with the San Francisco Giants and Atlanta Braves. That was until he got paid.
He was a disaster in Arizona, nearly doubling his career ERA to that point.
He never rebounded and was out of the game at 36 years old.
14. Jason Schmidt — Los Angeles Dodgers
Contract: Three years, $47 million
Return on investment: 10 games started, 3-6 W-L, 6.02 ERA, 43.1 IP, 30 Ks, -0.6 WAR
Bottom line: Jason Schmidt came into his own as the ace of some terrific Giants teams in the early-mid 2000s, making the All-Star team in 2006.
Something about Los Angeles did not agree with him. He battled injuries and was atrocious when he did play, leaving plenty to ask, "What happened?"
13. Jason Bay — New York Mets
Contract: Four years, $66 million
Return on investment: 288 games played, .234 BA, .687 OPS, 26 HR, 231 hits, 1.8 WAR
Bottom line: After hitting a career-high 36 home runs for the Boston Red Sox in 2009, Jason Bay was an utter disaster in New York.
A hitter who had posted better than a .900 OPS five times couldn’t crack .800 in any year with the Mets, when his durability also fell sharply.
The Mets released Bay in 2012 after three seasons, and he was out of baseball a year later.
12. Prince Fielder — Detroit Tigers
Contract: Nine years, $219 million
Return on investment: 324 games played, .295 BA, .878 OPS, 55 HR, 356 hits, 6.6 WAR
Bottom line: That number is correct. The Tigers gave Fielder $219 million, thinking he and Miguel Cabrera would terrorize American League pitching for a decade. Did not quite work out that way.
Fielder had two solid years, but showed significant regression in the second, and the team bit the bullet and sent him to Texas before his 30th birthday.
He was out of the game at 32.
11. Denny Neagle — Colorado Rockies
Contract: Five years, $51 million
Return on investment: 65 games started, 19-23 W-L, 5.57 ERA, 370.1 IP, 271 Ks, 1.3 WAR
Bottom line: The Rockies were determined to overhaul their rotation heading into 2001, and they spent nearly $200 million to do it, only for it to come immediately crumbling to the ground.
Denny Neagle showed serious regression when the Yankees acquired him in the middle of the 2000 season, and that continued in Colorado, where he didn’t post an ERA below 5.00 in any of his three seasons.
10. B.J. Upton — Atlanta Braves
Contract: Five years, $72.5 million
Return on investment: 267 games played, .198 BA, .593 OPS, 21 HR,180 hits, -2.1 WAR
Bottom line: B.J. Upton had just come off his best season as a pro with the Rays, belting 28 homers with 31 steals in 2012, when he cashed in for a big payday in Atlanta.
Upton struggled to hit the ball at all in the ATL, striking out 324 times to just 180 hits in his two years before being shipped to San Diego.
9. Wei-Yin Chen — Miami Marlins
Contract: Five years, $80 million
Return on investment: 53 games started, 13-18 W-L, 5.03 ERA, 293.2 IP, 241 Ks, -0.8 WAR
Bottom line: According to former Marlins president David Samson, Scott Boras sold the Marlins a false bill of goods in 2016, and they’re still paying for it.
After a few solid years as an Oriole, Wei-Yin Chen has been unreliable for Miami, and a massive overpay given his production.
8. Jacoby Ellsbury — New York Yankees
Contract: Seven years, $153 million
Return on investment: 520 games played, .264 BA, .716 OPS, 39 HR, 511 hits, 9.8 WAR
Bottom line: Jacoby Ellsbury’s production has been in line with his early years in Boston, with the exception of an insane output in 2011, but he has not been able to stay on the field.
It remains to be seen when he will wear pinstripes again, but the value has fallen well short of the big payday.
7. Barry Zito — San Francisco Giants
Contract: Seven years, $126 million
Return on investment: 197 games started, 63-80 W-L, 4.62 ERA, 1139.1 IP, 787 Ks, 2.4 WAR
Bottom line: Barry Zito became the highest-paid pitcher in major league history when he signed on the dotted line for San Francisco.
That also ramped up expectations, and Zito did not live up to his pre-Giants numbers, although he did have a couple solid years in the Bay.
6. Pablo Sandoval — Boston Red Sox
Contract: Five years, $95 million
Return on investment: 161 games played, .237 BA, .646 OPS, 14 HR, 136 hits, -2.1 WAR
Bottom line: One of the best pure hitters in baseball saw his skills seemingly evaporate the moment he stepped into Fenway Park.
Pablo Sandoval averaged a plus-.800 OPS in his seven years in San Francisco, and couldn’t crack .700 in less than a full season of at-bats in Boston.
He now is back with the Giants, but his hitting has not returned.
5. Carlos Silva — Seattle Mariners
Contract: Four years, $48 million
Return on investment: 34 games started, 5-18 W-L, 6.81 ERA, 183.2 IP, 79 Ks, -2.8 WAR
Bottom line: This is an odd one, because Carlos Silva never had a breakout season, posting a 4.31 career ERA at the time the Mariners decided to give him a solid payday.
His near-7.00 ERA in a season’s worth of starts was enough to bite the bullet and send him to the Chicago Cubs.
4. Carl Crawford — Boston Red Sox
Contract: Seven years, $142 million
Return on investment: 161 games played, .260 BA, .711 OPS, 14 HR, 162 hits, 0.9 WAR
Bottom line: Carl Crawford spent his formative big league years in Tampa Bay, racking up big steals numbers and four All-Star appearances for the Tampa Bay Rays.
His tenure in Boston was rocky at best, as he batted close to .220 for the bulk of his first year, was injured in his second and traded to the Dodgers with Josh Beckett, Adrian Gonzalez, Nick Punto and cash in August 2012.
3. Chris Davis — Baltimore Orioles
Contract: Seven years, $161 million
Return on investment: 422 games played, .199 BA, .684 OPS, 80 HR, 302 hits, -0.2 WAR
Bottom line: Even at the time, this contract felt like a massive overpay. But Chris Davis just had hit 47 homers for the Orioles in 2015.
The team chose to ignore his 208 strikeouts and outlier of an OPS and ponied up the money.
Since then, Davis has hit around the .200 mark in batting average and has struck out 621 times in three-plus years.
2. Mike Hampton — Colorado Rockies
Contract: Eight years, $121 million
Return on investment: 62 games started, 21-28 W-L, 5.75 ERA, 381.2 IP, 196 Ks, -1.6 WAR
Bottom line: For the first few months of Mike Hampton's Rockies tenure, this contract looked like a win-win deal for both sides as the left-hander earned a trip to the 2001 All-Star Game.
But things went off the rails in a hurry, and then Hampton fell off a cliff, posting a 7.41 ERA in the final half of his debut season.
He spent one more year in Colorado before being sent to Atlanta, where he more or less returned to his old form.
1. Josh Hamilton — Los Angeles Angels
Contract: Five years, $125 million
Return on investment: 240 games played, .255 BA, .741 OPS, 31 HR, 233 hits, 2.8 WAR
Bottom line: Josh Hamilton may have had the most up-and-down pro baseball career of all time.
The former top prospect got mixed up with drugs, came back and became an MVP-caliber player. Then, he fizzled out again after getting his big payday.
In 2015, the Angels traded him back to the Rangers, his former team, where he spent 50 games, prior to retiring after another battle with his addiction.