The 15 worst MLB free-agent signings of all time

The deal: Five years, $125 million. 

The debacle: Somehow, Hamilton’s time with the Angels managed to be worse than most worst-case scenarios presented at the time of his signing (and those were plentiful). Not only did Hamilton struggle greatly when actually healthy in the regular season — he posted a .255/.316/.426 slash line with only 32 homers in 240 games (he hit 43 in 148 games in his last year with the Rangers) — but he was 0-for-13 in the 2014 postseason as his 98-win team was eliminated by the wild-card Royals.

Then, the disastrous offseason that resulted in the trade that sent him back to the Rangers. The worst part, and what makes Hamilton sit on top of this list is, to actually get rid of him, the Angels paid Hamilton a ton of money to play for their division rival. Short of bringing a plague of locusts to town, it’s hard to see how this could have played out any worse for the franchise. 

The signing: 10 years, $240 million

The debacle: He just wasn’t the same player with the Angels that he was with the Cardinals. Almost like giving a player entering his Age 32 season a 10-year deal wasn’t a good idea. Pujols still hit a lot of home runs with the Angels (222, to be exact), but that was about all his body would allow; injuries, especially to his legs and feet, kept him from doing much else. In the final five years of his 10-year deal, Pujols played 545 games and hit 88 home runs, but he produced a minus-1.8 bWAR. Not a typo. 

But befitting a player who was a no-doubt Hall of Famer before he left St. Louis, his final year in the bigs — back with the Cardinals — restored his legacy, as he popped 24 homers, produced a 154 OPS+ and passed the 700-home run mark. 

The signing: Eight years, $121 million

The debacle: The Rockies were determined to overhaul their pitching staff after the 2000 season, and Hampton, the lefty who owned a career 3.44 ERA, was their answer. So they gave him gobs of money, but Denver's thin air rendered him highly ineffective (as it tends to do to breaking-ball pitchers). After just his second season in Colorado (and a 5.75 ERA in 62 stars), Hampton was traded away in a complicated three-team deal with the Marlins and Braves.

The signing: 7 years, $153 million

The debacle: We’ll start with this: Ellsbury’s deal with the Yankees was for seven years, but he played just four seasons in the majors after signing the deal. Injuries suck. Yankees fans seemingly hated the former Red Sox All-Star right from the beginning because he didn’t produce multiple seasons like his 2011 campaign in Boston, when he hit 32 homers, stole 39 bases, batted .321 and finished second in the AL MVP voting. Truth is, though, looking back his numbers weren’t horrible. His bWAR, year by year: 3.6 in 2014, his first with the Yankees, 1.8, 2.7, 1.8. Not up to the levels expected by the contract, of course, but not Joey Gallo, either. 

Spending the entire 2018 and 2019 seasons on the disabled list, for a variety of ailments, secured his legacy of infamy in the Bronx, though. 
 

The signing: 8 years, $184 million

The debacle: Look, flags fly forever. Especially in a place where a new title flag hadn’t flown in, well, forever. No doubt about that. Do the Cubs win the 2016 World Series without Heyward? Who knows. But they did win with Heyward, and that matters. That championship alone is reason enough to keep J-Hey from the top of this list. 

But it’s not enough to keep him off this list. In his walk-year season in St. Louis — the Cardinals had traded for him the previous offseason — Heyward produced a 6.9 bWAR, with a  .293/.359/.439 slash line, along with a 117 OPS+. He was heading into just his Age 26 season. There were very few reasons to think he wouldn’t be productive throughout the length of his eight-year deal with the Cubs. But, he wasn’t. 

Heyward has one year left on his deal, but the Cubs announced during the 2022 season that he won’t be back in 2023. His final numbers with Chicago: 744 games, 8.9 bWAR, .245/.323/.377 slash line, with an 86 OPS+.

The signing: Five years, $95 million

The debacle: Sandoval was coming off his second amazing World Series performance with the Giants when the Red Sox gave him this massive contract in November 2014 to take over the job at third base. Sandoval had hit .500 with three homers in helping San Francisco beat the Tigers in the 2012 World Series, then hit .429 with 12 hits in seven games as the Giants outlasted the Royals in the 2014 World Series. 

But his time in Boston was almost a complete disaster. He was often overweight, and never very productive on the field. In his first year with the Red Sox, Sandoval compiled a .245/.292/.366 slash line (all career worsts) with 10 homers in 126 games. He missed all but three games of the 2016 season with shoulder issues, and any optimism that bubbled up this spring with his slimmed-down physique quickly fizzled out. By the time the Red Sox designated him for assignment on July 14, he'd hit just .212 in 32 games. 

How much did Boston want him gone? He's still owed $67.1 million on his deal, and the Red Sox have to pay every cent. 

The signing: Five years, $72.5 million

The debacle: Two years shouldn’t be enough to call a five-year deal a complete bust, but in Upton’s case — then known as B.J. — it was enough.

He was awful on an epic level for the Braves (.198 average, -1.7 WAR) and to get rid of him and his contract, the franchise had to trade All-Star closer Craig Kimbrel to San Diego in the deal. So maybe it wasn’t a great idea to give all that money to a guy who batted just .242 in his previous four seasons and struck out more times in those four years than all but just three other players in the game (and hit at least 30 fewer homers that those three guys).

He split time between the Padres and the Blue Jays in 2016, hitting just .196 with Toronto in 57 games.

The signing: Seven years, $126 million

The debacle: For the most part, Zito stayed healthy in the Giants’ rotation for the life of the contract, and he did have some brilliant moments in a San Francisco uniform. In retrospect, maybe it wasn’t good to guarantee that much money to a guy who had a 4.05 ERA (and 4.57 FIP) in the three seasons before he reached free agency. Zito never had an ERA (or a FIP) better than 4.03 and finished his time with the Giants with a 4.62 ERA.

The signing: Five years, $51 million

The debacle: The same offseason that brought Mike Hampton to Denver also brought lefty Denny Neagle to the Rockies. His time with the franchise was a disaster. After three awful years (a 5.57 ERA), Neagle missed all of 2004 with injuries, then was charged with soliciting a prostitute in December 2004, ending his time with Colorado. Yep.

The signing: Four years, $39.9 million

The debacle: The Yankees have made a lot of bold moves on the free-agent market, but no one’s time in the Bronx went as poorly as the pitcher who was dubbed “American Idle” during his time with the Yankees. In his four years in — or out — of pinstripes, Pavano made just 26 starts and finished with a 5.00 ERA. He spent most of his time on the disabled list, including his famous “bruised buttocks” injury. 

The signing: Three years, $30 million

The debacle: Nobody, aside from Cubs GM Jim Hendry, apparently, was surprised this deal ended badly. Bradley was a disaster in his lone season — on and off the field — and after he was suspended the final 15 games of 2009, he was dumped to Seattle in an offseason deal that brought back Seattle’s worst free-agency decision of all time, Carlos Silva. 

The signing: Seven years, $142 million

The debacle: Crawford admittedly never felt comfortable in Boston, and he was only a shadow of the player he’d been for Tampa Bay (.296/.337/.444, average of 45 stolen bases). Because of injuries, he only played two of those seven years before he was included in a salary-dump trade to the Dodgers. He hit .260 with 23 stolen bases, total, in 161 games for the Red Sox.

After four seasons with the Dodgers, Crawford was released, and LA paid over $43 million for Crawford to not play for them in 2016 and 2017.

The signing: Five years, $50 million

The debacle: Matthews was an elite defensive outfielder from the moment he arrived in the majors, but had never been much of a hitter. Until his age-31 season for the Rangers, that is, when he produced a .313 batting average (his career mark to that point was .249), 19 homers and a 5.2 WAR. The Angels gave him riches based on that level of production, which he never came close to matching; in 370 games over three seasons, he hit just .248 and was traded to the Mets for Brian Stokes, a 30-year-old reliever with a career 5.02 ERA.

The signing: Five years, $65 million

The debacle: For whatever reasons — pressure of the money, change of scenery, hitter-friendly home ballpark, injury — Park was awful with the Rangers. He made 68 starts over four seasons and posted a 5.79 ERA before he was traded to San Diego. 

The signing: Five years, $65 million

The debacle: Belle hit 60 home runs during his first two seasons with the Orioles, a pretty good start to the long-term deal. But he never played in the bigs again, sidelined by a chronic hip condition kept him off the field.

The signing: Four years, $66 million

The debacle: Bay, who hit 36 home runs for Boston in 2009, was a disastrous signing for the Mets. He dealt with all kinds of injury issues and wasn’t very productive even when he was on the field; in 288 games over three seasons, he hit just 26 home runs and batted .234 before the team and player parted ways.

The signing: Six years, $80 million

The debacle: For two seasons, Vaughn was good (average of 34 homers and a .865 OPS) but didn’t produce up to the standards he set in Boston, where he was the 1995 MVP (he averaged 40 homers with a .986 OPS in the four years before he signed with the Angels). But he spent the 2001 season on the disabled list, then was traded to the Mets that December. 

The signing: Four years, $33 million

The debacle: Ortiz was a mess in Arizona. He made just 28 starts for the Diamondbacks — he was released in June of the second year of his four-year deal — and compiled an amazingly bad numbers: 7.00 ERA, 1.896 WHIP, 5.7 BB/9, to name just a few.