Sale, who just turned 33 last month, is starting the year on the 60-day injured list due to a stress fracture in his right rib cage. While it’s not related to the arm issues that have long plagued him, it’s yet another injury that keeps Boston’s largest pitching investment away from the field.
Following two All-Star seasons with the Sox in 2017 and ’18, the hard-throwing lefty signed a massive extension that looks worse by the year. So much so, it now ranks among the worst contracts handed out by MLB teams over the last 10 years.
So what are some of the other poor contracts we’ve seen across the last decade? There have been many, as you can expect from a sport with no salary cap governing its contracts. While many big deals have worked out favorably for the teams handing them out, several became albatrosses the second the ink dried.
For this exercise, we’re looking at the six worst contracts in MLB since the offseason leading into Opening Day 2012. This includes both free-agent deals and extensions and factors in the age of the player, contract length/amount, and overall performance after the contract was signed.
Honorable mentions: 1B Eric Hosmer (8/$144), 2B Robinson Cano (10/$240), DH Giancarlo Stanton (13/$325), SS Francisco Lindor (10/$341), SP David Price (7/$217), 3B Pablo Sandoval (5/$95)
6. RF Jason Heyward – Chicago Cubs
Contract: Eight years, $184 million in 2016
Yes, Jason Heyward’s impassioned rain delay speech might have helped motivate the Cubs to win their first World Series since 1908. But that is the highlight of J-Hey’s tenure on the North Side.
After five seasons with the Atlanta Braves and a one-year run with the St. Louis Cardinals, Heyward signed a massive eight-year contract with the Cubs following the 2015 season. Chicago viewed the smooth-fielding lefty as the final piece of the puzzle before it was ready to contend for a title.
That title came to fruition for the Cubbies, although Heyward has hardly been worth his exorbitant price tag. In 2016, the 27-year-old slashed a dismal .230/.306/.325 with seven homers. For the subsequent five seasons, he would eclipse 11 home runs once while offering average to below-average contact hitting near the bottom of Chicago’s lineup.
The Cubs’ front office has been unable to move on from the 32-year-old Heyward. As a result, they were forced to trade franchise icons Kris Bryant, Anthony Rizzo, and Javy Baez in a conscious effort to trim the payroll. Meanwhile, Heyward still has another two years and $49 million left on his overpriced contract.
5. SP Chris Sale – Boston Red Sox
Contract: Five years, $145 million in 2019
It was hard to name a better pitcher than Sale between 2012 and 2018. Following five All-Star seasons with the Chicago White Sox, Boston traded a prospect package headlined by Yoan Moncada in exchange for the 27-year-old ace in 2017. He would go on to have two more great seasons at Fenway Park, finishing top-four in Cy Young voting and winning a World Series in 2018.
But ever since the Sox inked Sale to that lucrative extension just before the 2019 season, it’s been nothing but a disaster.
In 2019, the year before his next contract actually kicked in, the lefty had a career-worst 4.40 ERA, though he still managed 218 strikeouts in 147.1 innings. However, he was shut down in August due to left elbow inflammation. In March 2020, he underwent Tommy John Surgery, keeping him on the shelf until Aug. 14, 2021. He gave Boston nine starts upon returning, making it through six full innings once.
Now, Sale is out for at least two months after fracturing his rib throwing batting practice in February. This will mean Sale hasn’t pitched a complete season since ’17, his first year in Boston.
The seven-time All-Star is under contract through 2024 with a vesting option for ’25. And to put the cherry on top, the Sox will pay him $50 million in deferred money between 2035 and 2039.
4. 1B Albert Pujols – Los Angeles Angels
Contract: 10 years, $240 million in 2012
When you think of bloated contracts for aging players, Albert Pujols’ deal with the Angels immediately comes to mind. So much so, we made sure the parameters included him, as his deal was technically signed in Dec. 2011.
Albert’s 11-year run with the Cardinals was the stuff of legends. 445 home runs, a 1.037 OPS, three MVPs, and two World Series victories were some of the accomplishments El Hombre had in St. Louis. Then he signed in Anaheim, where things started going … differently.
Pujols’ long tenure with the Angeles birthed a single All-Star appearance in 2015, his lone 40-homer season. In fact, The Machine only hit 30 dingers two other years. And while his power slowly evaporated, so did his elite approach at the plate, as he went from a Cardinals slash of .328/.420/.617 to an Angels slash of .256/.311/.447.
Just a few weeks into 2021, the final year of Albert’s deal, the Angels released him. In other words, they paid him $30 million to not play baseball for them anymore.
As Pujols finishes his career back where he began for one final year, his hand in mentoring the generational Mike Trout keeps this contract from being worse than number four on the list.
3. 1B Miguel Cabrera – Detroit Tigers
Contract: Eight years, $248 million in 2014
If Pujols was the best right-handed hitter of the 2000s, Miguel Cabrera was the best righty of the 2010s. Well, at least for the first half of the decade.
The Venezuelan won four batting titles, two MVPs, and a Triple Crown from 2011 through 2015. So in 2014, Detroit made its superstar slugger a Tiger for life, inking him to a deal that, combined with his previous contract, paid him through 2023. The extension also had two $30 million mutual options for 2024 and ’25.
Considering Cabrera was already 31 before the extension kicked in, few were expecting the contract to age gracefully. But it’s been far worse than anyone expected, as the future Hall of Famer showed serious decline almost immediately after the agreement officially began in 2016.
Following a lone All-Star campaign in 2016, Cabrera has failed to hit over 16 home runs or bat .300 in a season. His OPS, which routinely sat in the 1.000 range during his prime, was .701 in 2021 and .746 the year before that. And his combined WAR over the last five years is -1.1, meaning he’s been roughly one win worse than a replacement-level player.
Miggy is graciously handing the first base job to top prospect Spencer Torkelson for 2022. But that doesn’t change the fact that the 38-year-old still has two more guaranteed seasons to go, where he’ll earn another $64 million.
2. 1B Chris Davis – Baltimore Orioles
Contract: Seven years, $161 million in 2016
There is a strong case for Chris Davis to be number one on this list. Because from the second the towering slugger re-signed with the Orioles in 2016, everything came tumbling down.
The 6-foot-4, 255-lb first baseman reignited his career in Baltimore, leading the American League with 53 dingers in 2013 and 47 in 2015. As a free agent, Davis rejected offers from other teams and chose to return to Baltimore on a contract that would’ve gone through the 2022 season.
In his first year as a rich man, Crush slugged 38 homers but saw his OPS fall from .923 to .792. The next year, he only hit 26 homers while falling down to a .215 average and .732 OPS. But that’s just the start.
In 2018, he recorded the lowest batting average ever among qualified hitters, swatting an anemic .168 in 522 plate appearances. He wasn’t much better in 2019, hitting .179 and going on a historic 0-for-54 stretch at the plate. His last season was in the pandemic-shortened 2020, where he slashed .115/.164/.173 in 16 games.
Last season, a 35-year-old Davis announced his retirement while recovering from season-ending hip surgery. He will now make $17 million this year along with an additional $42 million in deferred payments across 15 years beginning in 2023.
1. LF Josh Hamilton – Los Angeles Angels
Contract: Five years, $125 million in 2013
Josh Hamilton’s shocking contract with the Angels isn’t more expensive than any of these previously-mentioned deals. But no MLB contract in the last 10 years went as poorly as this one, both on and off the field.
Armed with the reigning Rookie of the Year Trout plus the relatively new Pujols, LA stunned the baseball world by signing Hamilton. The 2010 MVP had made five straight All-Star appearances with the rival Texas Rangers and hit a career-high 43 home runs in 2012. In theory, adding the superstar left fielder would put the Angels over the edge and spring them into contention.
In 2013, the 32-year-old Hamilton managed to stay healthy but was far from productive. His 21 homers were a steep dropoff from the previous year, as was his .739 OPS. In 2014, he managed to play in only 89 games, hitting 10 homers with a .745 OPS. In the playoffs, he went 0-for-13 in LA’s three-game loss to the Kansas City Royals.
As he recovered from offseason shoulder surgery in 2015, it was revealed that Hamilton had relapsed into his drug addiction. Weeks later, the Angels traded the former MVP back to the Rangers, where he’d finish the year before never playing in the bigs again.
All in all, Hamilton hit .255 with 31 home runs during his 240 games with the Halos. But thanks to injuries, spats with fans, and a messy divorce that forced the Angels to pay $75 million over the three years he wasn’t on the team, there’s no topping this contract as the worst one baseball has seen in a decade.