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 There were 105 of those to choose from, but we further narrowed our scope to the 68 that are either no longer active or have been active for at least five seasons.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
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
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.