Ranking Miguel Cabrera and MLB's Worst $100 Million Signings
By now, the standard consumer of sports-related content surely will have come across at least one list of Major League Baseball's worst contracts.
A shortcoming they tend to share, however, is that they view things strictly from a position of hindsight.
By contrast, this list consists solely of 10 deals that were doomed to fail even before they ultimately did. We ranked them according to how much teams should have known better, as they were investing heavily in players whose extreme risk factors were obvious even at the time.
To avoid low-hanging fruit, we limited ourselves to only free-agent contracts and extensions worth at least $100 million. There were 105 of those to choose from, but we further narrowed our scope to the 68 that are either no longer active or have been active for at least five seasons.
The top 10 consists of three tiers. The first four, for inherently risky free-agent signings. The next three, for unwise and unnecessary contract extensions. And lastly, three for players who simply didn't have any business signing for nine figures.
First, we'll explain why we didn't pick some of the notoriously bad contracts that might spring to mind.
Honorable Mentions
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Dec. 15, 2006: Toronto Blue Jays Extend Vernon Wells
The Blue Jays locked Wells up on a seven-year, $126 million extension when he was established as an All-Star and Gold Glover. He was also only coming off his age-27 season, so it's hard to fault them for not anticipating that he would average just 1.1 rWAR per year after the deal began in 2008.
Dec. 11, 2010: Boston Red Sox Sign Carl Crawford
The reputation of Crawford's seven-year, $142 million pact with the Red Sox is, well, not good. What tends to be forgotten, though, is that he was coming off the best season of his career and that the reactions were accordingly positive at the time. Which is to say nobody predicted he would produce only 3.5 rWAR after the fact.
Nov. 14, 2011: Los Angeles Dodgers Extend Matt Kemp
Kemp was also coming off a career-defining season when he inked an eight-year, $160 million deal with the Dodgers. He had fallen one home run shy of a 40-40 season and finished second in the National League MVP voting. Alas, injuries undid his stardom to the point where he only produced 4.3 rWAR during the life of the deal.
Dec. 8, 2011: Los Angeles Angels Sign Albert Pujols
Reputationally speaking, Pujols' 10-year, $240 million contract with the Angels is the mother of all bad deals. But even if the contemporary reactions expressed wariness over the back half of it, few were outraged that the Angels had granted so much money to a three-time MVP and two-time World Series champion.
10. Nov. 30, 2016: New York Mets Sign Yoenis Cespedes
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The Deal: 4 years, $110 million
Pre-Deal WAR: 18.9
WAR During Contract: 2.7
This was, of course, the second deal that the New York Mets did with Yoenis Cespedes in free agency. In both cases, they could be forgiven for feeling attached to him.
Cespedes had transformed the team after coming over from the Detroit Tigers in a deadline-day trade in 2015, blasting 17 home runs in 57 games to spearhead a charge to the World Series. Further greatness followed in 2016, in which Cespedes hit 31 homers in only 132 games.
The circumstances that caused Cespedes to miss 30 games in 2016, however, should have been scrutinized further by the Mets.
Though issues with his right quadriceps landed him on the injured list just once, the injury nagged him even in games in which he played. It obviously didn't sap his power, but his defense and baserunning metrics each showed obvious red flags, as outlined by MLB Trade Rumors' Jeff Todd.
Sure enough, injuries limited Cespedes to 119 games across 2017 and 2018. Then none at all in 2019 and just eight in 2020. On the plus side from a team perspective, the Mets at least got to cut his salary for the latter season after he sustained an injury in a non-contractually sanctioned incident with a wild boar.
9. Dec. 15, 2012: Los Angeles Angels Sign of Josh Hamilton
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The Deal: 5 years, $125 million
Pre-Deal WAR: 25.0
WAR During Contract: 3.1
Two years after winning the American League MVP, Josh Hamilton once again performed like a superstar in 2012.
He hit 43 home runs—including four in one game—and drove in 128 runs, all while mostly playing a premium position in center field. So after narrowly missing a playoff berth in 2012, the Los Angeles Angels weren't entirely foolish to think that Hamilton could put them over the hump.
But as Tim Dierkes of MLB Trade Rumors wrote at the outset of the 2012-13 offseason, signing Hamilton for a substantial sum would nonetheless require a "special kind of recklessness."
It wasn't just Hamilton's well-documented struggles with addiction. He was also prone to injuries and inconsistency, including in 2012. He wasn't much better than replacement level over the final four months of the season, in which he notably missed games with caffeine-related vision issues.
That ended up being a sign of things to come. Hamilton simply never recaptured his stardom with the Angels, who sent him back to the Texas Rangers in 2015. That also proved to be his last major league season.
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8. Dec. 12, 2000: Colorado Rockies Sign Mike Hampton
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The Deal: 8 years, $121 million
Pre-Deal WAR: 18.1
WAR During Contract: 2.8
It was quite the shock when the Colorado Rockies made Mike Hampton the highest-paid player in baseball history, but they had their reasons.
They certainly had the offense of a contender during the 2000 season, but their pitching staff lagged far behind as it ranked second-to-last in the National League with a 5.29 ERA. Hampton, meanwhile, had pitched to a 3.02 ERA over the previous two campaigns.
Crucially, Hampton owed his success to what was the game's best sinker. In theory, it was precisely what he needed to thrive amid the thin air and huge open spaces of Coors Field.
It wasn't lost on the press, however, that Hampton had a 6.88 lifetime ERA in Denver despite his sinker. On account of his unspectacular strikeout and walk rates, the left-hander also had a razor-thin margin for error even with his sinker working in good order.
Unsurprisingly, that margin for error collapsed as Hampton racked up a 5.75 ERA in two seasons with the Rockies. They traded him in 2002, and he later missed the 2006 and 2007 seasons after having Tommy John surgery.
7. Jan. 21, 2016: Baltimore Orioles Sign Chris Davis
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The Deal: 7 years, $161 million
Pre-Deal WAR: 14.3
WAR During Contract: Minus-2.7
Chris Davis was a consistent power supply in his first four-and-a-half seasons with the Baltimore Orioles. Never more so than in 2013 and 2015, when he led the majors with 53 and 47 home runs, respectively.
Moreover, this was during a time when offense was hard to come by. And while a leaguewide surge in home runs did help resuscitate run scoring in the latter half of 2015, nobody knew for sure if it would last.
But while all this amounted to some justification for Davis' deal, the caveats were very much there.
Though Davis had been prone to strikeouts before, he was that much more so as he led MLB in strikeout rate in both 2014 and 2015. Considering that he wasn't an elite walk magnet, baserunner or defender, he would need to keep his power alive to avoid a total collapse of his value.
To the tune of 38 home runs in 2016, that went OK at first. But it wasn't long before Davis couldn't buy a hit, much less a home run. He last played on a regular basis in 2019 and retired last August after undergoing hip surgery.
6. April 26, 2010: Philadelphia Phillies Extend Ryan Howard
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The Deal: 5 years, $125 million
Pre-Deal WAR: 19.5
WAR During Contract: Minus-4.8
Because Jim Thome was entrenched at first base for the Philadelphia Phillies in 2003 and 2004, Ryan Howard had to wait longer than he deserved before he finally got his shot in 2005.
The wait proved worth it. He won the NL Rookie of the Year in '05 and then the NL MVP in 2006. As he hit 14 more home runs than anyone else from 2005 to 2009, his power was simply unrivaled.
Despite all this, there was disgust in the air when the Phillies extended Howard in April 2010. Perhaps nobody was more fed up than ESPN's Rob Neyer, who called the contract "a testament to old-school ignorance."
Howard was powerful, yes, but the other aspects of his game were so weak that he averaged just 2.8 rWAR from 2007 to 2009. He was also already past 30 and not even due for free agency until after 2011.
As if Howard's contract wasn't doomed enough, the last thing he did on the diamond before the pact began in 2012 was tear his Achilles. He wasn't the same after that, never hitting so many as 30 homers in any of his last five seasons.
5. Feb. 26, 2012: Washington Nationals Extend 3B Ryan Zimmerman
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The Deal: 6 years, $100 million
Pre-Deal WAR: 33.7
WAR During Contract: 5.2
Contrary to Howard's extension with the Phillies, the Washington Nationals weren't necessarily risking the wrath of the aging curve when they extended Ryan Zimmerman's deal before the 2012 season.
Though he was likewise two years from free agency, he was only 27 years old and came with a track record of well-rounded production. In 2009 and 2010, specifically, he nabbed two Silver Sluggers and a Gold Glove and was one of three National Leaguers to produce at least 6.0 rWAR both years.
The catch, though, was that the 2011 season had arguably turned Zimmerman into damaged goods.
He missed 60 games after having abdominal surgery in March, and both his offense and defense suffered upon his return. He ended up with just a 118 OPS+ and 12 home runs for the former. In spite of his new throwing mechanics, his metrics for the latter went from well above to well below average.
After 2011, subsequent issues with his throwing shoulder kept Zimmerman's defensive quality stuck in the past. And while his bat did recover, his 36-homer outburst in 2017 was his only star-caliber performance during the life of his contract from 2014 to 2019.
4. March 27, 2014: Detroit Tigers Extend Miguel Cabrera
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The Deal: 8 years, $248 million
Pre-Deal WAR: 64.8
WAR During Contract: 4.0
If you take the biggest red flags from Howard's extension and combine them with the biggest from Zimmerman's, what you get is Miguel Cabrera's second contract with the Tigers.
Without question, the accolades were there. The last decade had seen Cabrera average a 157 OPS+ and 35 home runs per season, with MVP-winning peaks in 2012 and 2013.
One problem, however, was that Cabrera had been hobbled by core injuries down the stretch in 2013. His swing was all arms and shoulders by the end of the year, so he naturally had to have surgery to repair everything.
The other problem was twofold. Cabrera was set to turn 31 years old mere weeks after signing his new deal. What's more, it wouldn't kick in until after his existing contract ran out after the 2015 season.
All this contributed to Cabrera's new deal being widely panned. And while he did begin it with an excellent campaign in 2016, since then everyone's worst fears have been realized as he's been trapped in a replacement-level purgatory. It seems likely that the Tigers will release him before his deal ends in 2023.
3. Feb. 20, 2014: Cincinnati Reds Extend Homer Bailey
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The Deal: 6 years, $105 million
Pre-Deal WAR: 5.1
WAR During Contract: 0.5
When the Cincinnati Reds extended Homer Bailey's contract in the winter of 2014, the reaction wasn't so much one of outrage as befuddlement.
To be fair, it was an upside play. Bailey had mediocre career numbers, yes, but he'd shown marked improvement in 2012 and 2013. He pitched no-hitters both years, and in the latter he had achieved a career-best strikeout rate with the help of sustained mid-90s velocity.
Even in those years, however, Bailey's 4.7 rWAR didn't even place him in the top 40 among all pitchers. He was also 27 years old and thus at a point in his career where his abilities had likely peaked.
What's more, Bailey also came with injury risk. Though he had been healthy enough to cross the 200-inning threshold in 2012 and 2013, he had experienced problems with his shoulder in 2010 and 2011.
All this risk invariably blew up in the Reds' faces. Bailey immediately took a step backward in 2014, and he barely pitched in 2015 and 2016 after having Tommy John surgery. His tenure with the Reds ended in 2018 when they traded him to the Los Angeles Dodgers in a salary dump.
2. Nov. 29, 2015: Detroit Tigers Sign RHP Jordan Zimmermann
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The Deal: 5 years, $110 million
Pre-Deal WAR: 19.5
WAR During Contract: 0.8
Though little of it had to do with Cabrera, it didn't take long for things to get bleak in Detroit after the Tigers committed $248 million to him.
They made the playoffs in 2014 only to get promptly swept out by the Orioles. They then slipped well below .500 in 2015, raising questions about how much (if at all) the team's championship window was still open.
To this end, the Tigers' deal with Jordan Zimmermann perhaps would have been admirable if it wasn't such an obvious risk. To quote Keith Law, then of ESPN, it was seemingly a case of the club "paying for a version of Zimmermann that no longer exists."
The right-hander, who was due to turn 30 in May 2016, had been an All-Star and down-ballot Cy Young Award contender in 2013 and 2014. But in 2015, he lost nearly 1 mph off his average fastball and pitched to an only slightly above-average 108 ERA+ and a below-average strikeout rate of 7.3 per nine innings.
Factoring in that Zimmermann was also a Tommy John survivor, it wasn't unexpected that he struggled with injuries and inconsistency during his five years with Detroit. He retired last May.
1. Dec. 29, 2006: San Francisco Giants Sign Barry Zito
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The Deal: 7 years, $126 million
Pre-Deal WAR: 31.0
WAR During Contract: 2.4
If super-agent Scott Boras ever finds himself needing to convince a skeptical player to hire him, he only needs to say the name Barry Zito.
The curveballing southpaw was absolutely an ace in his early seasons with the Oakland Athletics, notably capturing the American League Cy Young Award in 2002 as he pitched to a 138 ERA+ from 2001 to 2003.
Yet Zito wasn't that guy from 2004 to 2006 with Oakland. Though he kept churning out 200 innings annually, his run prevention slipped to a more modest 110 ERA+. And after spiking in 2005, his average fastball velocity fell by roughly 2 mph to just 85.8 mph the following season.
Clearly, he was an odd choice for any team to want to build around. But especially the San Francisco Giants, who viewed Zito as the "franchise player" who would fill Barry Bonds' shoes when he retired.
To be fair, Zito did have a moment as such a player during the Giants' championship run in 2012. Yet this was after, much to his dismay, he was left out of the club's previous championship run in 2010. And on the whole, 2012 only does so much to redeem the ugly 87 ERA+ Zito had in seven years as a Giant.
Stats courtesy of Baseball Reference and FanGraphs.
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