Contracts. They can’t be undone (well, in most cases) and athletes won’t work without them.
Those signed sheets of paper, riddled with clauses, conditional terms, and fine-print addendums, can — and have! — grown into the bane of professional sports. But as much as they are a reality, they are necessary, and with this necessity come moments of repent.
Major League Baseball isn’t alone in the world of worst contracts, but the league certainly has had its share of bad examples and without a cap, the sky is the limit for well-to-do teams.
Whether it is the result of overpaid non-performers, ill-timed due to long-term injuries, or plain-old bad luck, all of it matters absolutely nil when the millions (at times, hundreds of millions) of dollars are seen flushed down the toilet, with nothing left to do but assess the damage done.
In that regard, the New York Yankees are sure hoping they get good value out of the remainder of Giancarlo Stanton’s monstrous $325 million contract that doesn’t run out until 2028.
With all the millions being thrown around, it warrants recounting some of the worst contracts in the history of the game, many of which were doled out in recent memory.
20. Vernon Wells – Toronto Blue Jays
It a given that good to great players get paid for what they did before, not what they do after signing a big contract. In the Toronto Blue Jays case, management probably wished they’d had a crystal ball when they handed All-Star outfielder Vernon Wells a seven-year, $126 million contract after his monster 2006 season. It is tied for the 60th biggest contract in sports, all-time. By 2007, his batting average dipped nearly 60 points from 2006 (.303 to .245) and his homers were halved (32 to 16). In an injury shortened 2008 season, he did make a marginal comeback, hitting .300 in 108 games, but for five more seasons, two with Toronto, two with the Angels and one with the Yankees, Wells was strictly ho-hum at the plate. It’s a good thing Wells was an exemplary human being, what with the induction into the Baseball Humanitarians Hall of Fame in 2010.
19. Matt Cain – San Francisco Giants
For a five-year period late in the last decade and into this one, there weren’t many pitchers as durable or as busy as the Giants Matt Cain. Starting in 2007, the big rightie started 32 games and pitched 200 innings. For the next five campaigns, Cain started anywhere from 33 to 34 games and recorded well over 200 innings each year. In that time his record was 70-65 and his ERA clocking in from a low of 2.79 in 2012 to a high of 3.76 in 2008. For all his hard work, the Giants rewarded him with a six-year, $112.5 million extension in early in 2012. He rewarded the team with a perfect game (the 22nd in major league history) during that 2012 season, his best in the majors, but it’s been all downhill since. After going 8-10 with a 4.00 ERA in 30 starts in 2013, the three-time All-Star has been hampered by injuries and inconsistency. His 2017 year was a “comeback” of sorts, as he started over 20 games for the first time since 2013 (23), but his numbers were among the most dismal. He went 3-11, with a 5.43 ERA and career worst 1.657 WHIP and then promptly retired.
18. Yasmany Tomas – Arizona Diamondbacks
The only thing the D-Backs could be forgiven for in handing so-so OF/3B Yasmany Tomas a fat six-year, $68.5 million contract in late 2014 was not being left behind in the Cuban baseball player sweepstakes. As his countrymen Jose Abreu and Rusney Castillo (more on him later) signed bigger deals elsewhere, Arizona thought they were getting a pretty good bargain. However, the big Cuban slugger was pretty one-dimensional, which has come back to haunt Arizona, and cost GM Dave Stewart his job in 2016. Tomas, prized for his booming bat, hit just nine homers in 118 games in 2015, while striking out 110 times and drawing just 17 walks. He was better in 2016, smacking 31 homers, but still whiffed 136 times and posted a lackluster .966 fielding percentage in the outfield. Surgery cut short what was turning into a mediocre campaign in 2017, where Tomas appeared in 47 games, hitting eight homers and registering a .294 OBP and -0.5 WAR.
17. James Shields – Chicago White Sox
Like Matt Cain, Chicago White Sox hurler James Shields is — well, was — one of those dependable and durable starting pitchers every team needs. He just hasn’t been outstanding, save for one year, but sure gets paid like it. In early 2015, the San Diego Padres reward the one-time All-Star for all his years of hard work elsewhere, inking him to a four-year, $75 million contract. He did start over 30 games (33) for the ninth straight season, but he gave up an average of one homer every game (including one to Bartolo Colon) to have the highest total in the NL, along with a 13-7 record and 3.91 ERA. He started slowly, going 2-7 with a 4.28 ERA in 11 starts (nine homers against) and was shipped to the Chicago White Sox, who are now overpaying him. In 22 starts with the Chisox, Shield surrendered an eye-popping 31 homers against in 22 starts and finished 4-12, including a lousy 6.77 ERA. His 2017 year was an “improvement” as he posted a 5-7 ledger with 5.23 ERA and just 27 homers against in 21 starts. Chicago has to be choking on the fact they are on the hook for another $18.75 million this season.
16. Rusney Castillo – Boston Red Sox
The Boston Red Sox will pay Rusney Castillo $11 million not to play for them in 2018. In 2014 the Bosox tripped all over themselves to sign the speedy centerfielder to a fat seven-year, $72.5 million pact. He’s been making them regret it ever since. Since 2014 he’s played in just 99 big league games, registering a .262 batting average, below average OBP of .301 and mustered 21 extra base hits, seven stolen bases and 35 RBI. Castillo, 30, has spent the majority of his well-paid time with AAA Pawtucket of the International League the last two seasons. He’s been decent there, but if there is a poster boy for “buried money” he is the face of it. On whatever bright side is left, he did get an invite to spring training this year.
15. Ubaldo Jimenez – Baltimore Orioles
At least the Orioles have washed their hands of a terrible contract. Finally. Before the start of the 2014 season, the Orioles handed Jimenez a four-year, $50 million contract — not bad for a guy who struggled with control of his pitches and had one good MLB season (2010 with Colorado). The O’s should weighted his bounceback 2013 season with Cleveland against a pretty terrible 2012. In 2012, he went 9-17 with a 5.40 ERA, gaudy 1.613 WHIP and an AL high 17 wild pitches. He went 13-9 in 2013, lowered his ERA to 3.30 and his WHIP to a still unimpressive 1.330. He did not impress in Baltimore at all, despite being paid $12.5 million a year. Overall, he started 104 of 117 games, with a 5.22 ERA (6.81 in 2017), 1.496 WHIP and 32-42 record. Good luck to him finding a contract in free agency.
14. Pablo Sandoval – San Francisco Giants
This season, the San Francisco Giants will finally pay Pablo Sandoval what he’s worth. At $535,000, it’s a far cry from the $18 million average he was making in Boston for a couple of years after signing a whopping five-year, $90 million deal in late 2014. Kung Fu Panda, who was a two-time All-Star with the Giants and played seven good to great seasons with them, took the money and ran to Beantown. Well, let’s say the portly third baseman waddled there and struggled to maintain a healthy weight for all of 161 games in parts of three seasons. He had just six at bats in 2016 and was shut down for shoulder surgery and then struggled badly in 2017, hitting just .212 in 32 games with four homers before being bought out and waived by Boston. The Giants picked him up for the league minimum and he batted .225 with five homers and 20 RBI in 47 games. Yep, that’s (sort of) worth $535,000.
13. Matt Garza – Milwaukee Brewers
Matt Garza was so bad near the end of the 2015 season that the Milwaukee Brewers shut him down with a month to go — and he wasn’t injured. Good but never great, the Brew Crew signed the veteran starter in early 2014 to what was then the richest contract in Brewers’ history, four years and $52 million. However, Garza was already 30 when he signed that deal and in due time lost velocity off a once prime fastball. He was OK in 2014 but his 2015 campaign was lousy, before he was sat down unceremoniously that September. He posted a 6-14 record in 26 games, with a terrible 5.63 ERA and 1.567 WHIP. Over the course of the final two seasons of that ludicrously rich pact, Garza wen 12-17 in 41 starts and had a WHIP just under 1.500. He is a free agent in 2018 and will find it hard to get a contract worth even 1/10th what he was paid the last four years.
12. Hector Olivera – Los Angeles Dodgers
The Los Angeles Dodgers included a sweet, sweet $28 million signing bonus in the $62.5 million contract they gave Hector Olivera in March 2015. Clearly, they thought he could be an immediate upgrade on what they had at third. Less than a year later, “bust” was the only word being associated with Olivera. He ended up with the Braves in July 2015 and proceeded to be a very sub-par major league hitter. He logged just a .674 OPS in 30 career games and had all of eight extra base hits. He went from mediocre to downright toxic in 2016, getting arrested for assault in April that year, subsequently suspended for 82 games in May and then convicted and sentenced to jail time in September. He hasn’t been seen since, though the Dodgers are still on the hook for $4.6 million of that signing bonus.
11. Jose Reyes – New York Mets
After six mostly uninspiring and controversy fueled seasons (he was suspended 51 games in 2016 for alleged domestic violence), shortstop Jose Reyes six-year, $106 million contract he signed with Miami way back in 2012 has finally run its course. In those six years, Reyes was traded to Toronto after a lone great season with the Marlins in 2012 and the Blue Jays were so unimpressed with his lack of defence they flipped him to Colorado at the 2015 deadline for Troy Tulowitzki. He was neither very good, nor very bad, in 47 games with the Rockies after that, however, in the aftermath of the suspension he was bought out of that contract and designated for assignment, where he was picked up for a second go around with the New York Mets. They paid him the league minimum for parts of two seasons and he is officially a free agent in 2018.
10. Juan Uribe – Los Angeles Dodgers
In 2016, his last mediocre year in the majors, Juan Uribe made a very modest, by MLB standards, salary of $4 million. What we take issue with was Uribe’s previous contract extension with the Dodgers, which, while nowhere remotely near the hundreds of millions that have been shelled out to many of the MLB players that reside on this list, was still an awful contract. The $21 million over three years the Dodgers paid to the veteran infielder between 2011 and 2013 netted the team one of the worst hitters in all its 130-year history. Uribe hit .191/.258/.284 with two home runs in 66 games in 2012. The year previous: the six foot slugger hit .204/.264/.293, with four home runs over a 77-game campaign. In 2014, after signing a two-year, $15 million extension, Uribe did hit .311, but had just nine homers in 103 games.
9. Jayson Werth – Washington Nationals
Jayson Werth’s contract is a perfect example of paying for what a man has done previously. After an all-star campaign with Philadelphia in 2009, followed by seven homers in Phillies run to a World Series triumph and then another great year in 201o the hirsute slugger rewarded his new club with a horrendous 2011 campaign, highlighted by a June where he boasted a .154 batting average, a .291 on-base percentage, and a .286 slugging percentage. In 2012, Werth broke his left wrist on a diving catch, against his ex-team no less, missing exactly half the schedule. In 2013, Werth finished 13th in NL MVP voting after batting .318 with 25 homers and 82 RBI and had a decent 2014, hitting .292 with 16 HR and 82 RBI. It’s been a severely sliding scale since, as he hit .221 an injury filled 2015 and “improved” to .244 in 2016. Now a free agent, Werth managed just 70 games in 2017 for his $21 million, hitting .226 with 1o homers.
8. Albert Pujols – Los Angeles Angels
In November, 2011, Pujols joined the Anaheim Angels, with owner Arte Moreno — who is probably cursing it now — inking the former three-time NL MVP for $240 million over a ten-year period. The 30-something slugger saw his numbers steadily decline to .258/.330/.437 in 2013 (from .299/.366/.541 in 2011 with St. Louis), which was well below his career average and drive in 95. He did bounce back in 2016 with a 31 HR, 119 RBI season, but his overall numbers, again, were far below the halcyon days in the Gateway City. What’s clear is the Santo Domingo native is past the beast-like consistency he showed with cards, if his .241 average and crummy .286 OBP in 2017 were any indication. That massive contract, which has probably precluded the middling Halos from signing decent pitchers, also sees him make a million dollars more each year, from $26 million last season to $30 million in 2021, when he’s 41 (and most likely out of baseball).
7. Prince Fielder, Texas Rangers
In 2012, the Detroit Tigers signed the portly Fielder to a 9-year, $214 million contract, which is still the ninth richest deal ever signed. In short, it seemed like money well spent, as Fielder hit 228 homers and drove in 646 runs in six seasons with Milwaukee between 2006 and 2011. Fielder did hit well during his two seasons in Detroit, but his post-season numbers left the Tigers cold, leading to a trade following the 2013 season. He had a .071 batting average in a world series sweep at the hands of the San Francisco Giants in 2012, only to follow that up with an equally dismal turnout in the 2013 playoffs, when he hit .182 in the ALCS against Boston with no homers and no RBI. Fielder faded in the worst possible way and was dealt immediately following the season, with the Tigers having to eat $30 million in salary. Fielder faded badly in Texas, with the 2015 All-Star season being the lone bright spot. As for his lone post-season appearance with Texas, the ALDS against Toronto, he hit .150, with one RBI. He was out of baseball after the 2016 season.
6. Johan Santana – New York Mets
Pre-Clayton Kershaw, Johan Santana was one of the most feared southpaws in baseball. The Venezualan wonder won two Cy Young awards with the Minnesota Twins in 2004 and 2006 and was in the running five years straight. Thus, it seemed like a good idea for the Mets, who acquired him in a trade with the Twins in February 2008, to lock up the then 28-year-old long term, to the tune of seven years and $137.5 million. He had a Cy Young worthy 2008 with New York, going 16-7, but by 2013 and two full campaigns on the DL (2011 and ’13) the Mets were forced to buy out Santana’s contract, shelling out $5.5 million to pay off the lefthander’s $25 million option for 2014. While he did toss a no-hitter in 2012, his dismal numbers and career-ending injuries make his contract one of the worst ever signed. After an ill-fated tryout with Toronto in 2015, Santana is still a free agent looking for a home.
5. Melvin Upton Jr. – San Diego Padres
When managers are discussing “bad contracts” or players to “dump”, the man formerly known as B.J. Upton immediately springs to mind, especially for the Atlanta Braves. Early in his career with Tampa Bay, the Norfolk, Virginia native was a dual threat offensively, hitting for power (113 HR between 2007-12) and stealing bases (217 in six seasons). After a stellar 2012 season, Upton signed the largest free agent contract (then) in Braves history, a five-year, $72.5 million deal. What he gave the Braves for that pact was just a whole lot of grief, his reputation as being a slacker following him (he was disciplined twice in Tampa for lack of hustle). Those incidences should have been a harbinger of things to come, as Upton didn’t put in the work to improve a terrible .184 batting average in 2013, along with the worst strikeout rate (151 in just 446 plate appearances) in the the National League. The Braves tired of his act and dealt him to San Diego, where he improved somewhat, later getting short look-see from Toronto. He’s been out of baseball since 2016.
4. Barry Zito – San Francisco Giants
On Dec. 29, 2006, Barry Zito signed a then historic seven-year deal with the San Francisco Giants, a seven-year pact worth $126 million, plus an $18 million option for 2014 with a $7 million buyout. At the time, Zito’s contract was the most for any pitcher in MLB history. The Giants saw a 28-year-old inning eater (six straight years of 200+ innings) and Cy Young winner (he was 23-5 in 2002) and lured him across the bay from the Athletics. The Giants, sadly, would never get 200 innings out of Zito in seven seasons and would see his ERA balloon from 3.83 in 2006 with Oakland to 5.15 in 2008. He posted a 63-80 record and a 4.62 ERA in 197 starts and for the Giants between 2007 and 2013, after going 102-61 with Oakland. The Giants declined the option in 2014, which is still payable in installments with 1% interest tacked on each year through 2020. His only saving grace was a win for the champion Giants during the 2012 World Series.
3. Ryan Howard, Philadelphia Phillies
Ryan Howard quietly slipped away from baseball in 2016, hitting a horrible .196 with 25 homers, just four years removed from signing a lucrative $125 million deal with the Phillies prior to the 2012 season. The 2006 NL MVP and power hitter was coming off his sixth straight year of finishing among the top 10 in National League MVP voting when he signed the extension of his dreams at age 32. It has been all downhill since. Between 2012 and 2013 he missed 173 games and saw his average numbers tumble across the board. He rebounded in 2014 to hit 23 homers and 95 RBI, but led the National League in strikeouts for the second time in his career with 190, while batting a dismal .223 and slugging just .380. In 2015, the albatross that is that contract loomed larger, with his RBI total falling by 18. His defence, or lack thereof, went from OK to terrible in 2016, when he made 11 errors on just 613 chances. Coupled with his tepid bat, it hastened his departure.
2. Carl Crawford, Los Angeles Dodgers
What is it about former Tampa Bay Rays who flounder once they leave the Florida city? In December 2010, Crawford had just come off a fourth All-Star campaign in nine seasons, along with his first Gold Glove and Silver Slugger awards. The triples and base stealing machine (he led the AL in those categories four times each) became a free agent and cashed in with the Boston Red Sox in late 2010, to the tune of an astounding $142 million over seven years. It must have been a great Christmas gift for the outfielder, who then went on to struggle in 2011, batting just .255 (after a .307 season in 2010) with 18 stolen bases after swiping 47 in 2010. He would play all of 31 games in 2012 and have season-ending Tommy John surgery. He was subsequently traded to the Dodgers and added fuel to an unhappy chorus about his play by calling Boston “toxic.” He enjoyed a bit of a renaissance with the Dodgers in 2013-14, but the injury bug bit again and his numbers declined precipitously in the last two seasons of his career, which ended after just 30 games (.185 batting average) in 2016.
1. Alex Rodriguez, NY Yankees
It must have chuffed the egotistical Rodriguez that Miami’s Giancarlo Stanton inked a deal that dwarfed his own massive contract by $50 million. And it’s ironic now that Stanton is a Bronx Bomber. Don’t get us wrong, the three-time MVP will surely go down as one of the top third basemen/DH the game has known (with an asterisk forever attached because of alleged PED use). But that astronomical 10-year, $275 million pact he signed in 2008 slowly became the albatross of albatrosses around Yankees management’s neck. He took a lot of grief for bad years in 2011 and 2012, rightly so, hitting just 34 total homers and then playing just 44 games in 2013 before being punished severely by major league baseball and missing a whole season. The 33-homer campaign of 2015 was a one-off, especially after he hit .200 in 65 games during the 2016 season, with nine homers. He didn’t get quite the self-congratulatory retirement tour he probably envisioned, slowly phased out in the waning months of 2016.