Dead money: Which players have the worst contracts in baseball?

Think Ryan Howard's deal (five years, $125M) is bad? Say hello to Prince Fielder (nine years, $214 million) and Rusney Castillo (seven years, $72.5 million).

Don’t look for Ryan Howard in the Phillies' lineup this weekend; he won’t be there. Instead, he’ll be on the bench, where manager Pete Mackanin has stationed him for what has been reported as “at least the next three games.” This is the closest the Phillies have come yet to acknowledging that Howard and the $125 million extension they signed him to in 2010 is a sunk cost. Indeed, that extension will go down as one of the worst contracts in major league history. With just four months remaining on the contract, Howard has been worth 4.4 wins below replacement since the extension kicked in in 2012, making every last cent of that $125 million wasted money.

Inspired by Howard, below is a position-by-position listing of the worst current contracts in baseball. It has been done systematically, calculating the dollars per marginal win (that is, each win above replacement level or point of WAR, using Baseball-Reference.com’s formula) for full term of each contract using accumulated WAR through Thursday’s games and projecting future performance. The latter was calculated by pro-rating each player's performance this season over 162 team games to get full-season figure for 2016. I then used a 5/4/3 weighting of the 2014 to '16 seasons to project a '17 value, then—following the same system used for our off-season What’s He Really Worth series—deducted 0.5 bWAR per season for hitters age 30 or older and 0.7 bWAR per season for pitchers age 30 or older.

Research was limited to contracts with a total value of $50 million or more. Billy Butler has been every bit as bad as Howard since signing with the A’s (-1.4 bWAR in just one and a third seasons), but, even to a small-market team like Oakland, his three-year, $30 million contract isn’t crippling. I also did not consider any contracts for which less than a full year has elapsed. That means you won’t see any of this off-season’s big signings here, nor will you see extensions that just kicked in, such as those of Brewers outfielder Ryan Braun, Tigers first baseman Miguel Cabrera or Red Sox pitcher Rick Porcello.

Here, then, are the worst contracts in baseball at every position, according to dollars per marginal win.

First Base

Ryan Howard, Phillies
Contract: Five years, $125 million
Accumulated bWAR: -4.4
Projected bWAR: -1.4
Dollars per marginal win: Sunk cost

It’s tempting to say the Phillies would have done as well by simply setting fire to that $125 million, but between taxes and Howard’s charitable efforts, at least some of that money went to deserving recipients.

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good job by #phillies to sign superstar ryan howard to a 5-year contract extension

— Jon Heyman (@JonHeyman) April 26, 2010

Second Base

Starlin Castro, Yankees
Contract: Seven years, $60 million
Accumulated bWAR: 2.2
Projected bWAR: 1.6
Dollars per marginal win: $15.8 million

Castro, who was traded from the Cubs to the Yankees last off-season, made a great first impression in New York during opening week and has hit for more power in pinstripes than he ever did in Chicago, but he nonetheless enters Friday’s action with a mere 87 OPS+ on the season. Factor in poor play in the field, and he grades out as a replacement-level player this year. Given that he was worth just 0.6 WAR in 2015, there’s not much optimism in the numbers for the final three years of his contract, even though they will take place in his prime age-27 to 29 seasons. Kudos to the Cubs for passing the last $38 million on this deal off on the Yankees and using the savings to sign Ben Zobrist.

Shortstop 

Jose Reyes, Rockies
Contract: Six years, $106 million
Accumulated bWAR: 8.9
Projected bWAR: 2.4
Dollars per marginal win: $9.3 million

Expecting Reyes to be worth 2.4 WAR over the remainder of his contract—which expires after next season with a $4 million buyout of his '18 option—is extremely optimistic. That number was arrived at by projecting Reyes’s 2016 bWAR total using a 5/4/3 weighting of his '13 to '15 seasons, then halving that total to reflect his missing the first half of the season due to a domestic violence suspension and using it to project his '17 total, again using a 5/4/3 weighting.

That assumes, however, that Reyes will find playing time over the final year and a half of his contract, which is not a given. Trevor Story has fully established himself as the Rockies' shortstop in Reyes’s absence, and given the veteran's poor showing last year (0.4 bWAR in 116 games) and legal trouble this year, it’s unclear that any other team would take him no matter how much of his $22 million salary for next year Colorado is willing to eat.

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Third Base 

Pablo Sandoval, Red Sox
Contract: Five years, $95 million
Accumulated bWAR: -1.1
Projected bWAR: 0.0
Dollars per marginal win: Sunk cost

Like Reyes, Sandoval hasn’t played at all this season and has effectively been replaced by a young, team-controlled player who seems unlikely to give his position back. In Boston, that player is Travis Shaw, who has been outstanding at third base and who will be under team control beyond the end of Sandoval’s contract. Sandoval, meanwhile, will miss the entire season following surgery to repair a torn labrum in his left shoulder. It’s unlikely that he’ll be more than a replacement level reserve upon his return next year.

Catcher

Miguel Montero, Cubs
Contract: Five years, $60 million
Accumulated bWAR: 2.4
Projected bWAR: -0.5
Dollars per marginal win: $28.6 million

Montero was worth 4.1 WAR in each of the seasons before he signed this extension with the Diamondbacks, but he hasn’t been worth more than 1.8 WAR over a full season since. This season, he has sunk below replacement level with an 88 OPS+ and poor play in the field that includes throwing out just one of 18 attempting base stealers. A catcher who turns 33 in early July, Montero doesn’t fit the description of a player likely to rebound over the final year and a half of his contract. Fortunately for the Cubs, David Ross has found the fountain of youth in his final season.

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Outfield 

Yasmany Tomas, Diamondbacks
Contract: Six years, $68.5 million
Accumulated bWAR: -1.4
Projected bWAR: -1.5
Dollars per marginal win: Sunk cost

Hector Olivera, Braves
Contract: Six years, $62.5 million
Accumulated bWAR: -0.3
Projected bWAR: 0.0
Dollars per marginal win: Sunk cost

Rusney Castillo, Red Sox
Contract: Seven years, $72.5 million
Accumulated bWAR: 1.8
Projected bWAR: -0.7
Dollars per marginal win: $65.9 million

You could argue that it’s too early to come down so hard on these three players, all of whom defected from Cuba and signed massive major league deals in the last two years. The counterpoint is that Castillo will turn 29 in July and hit just .241/.302/.317 in Triple A this year before Jackey Bradley Jr.’s paternity leave made temporary room for him on Boston's roster. With Bradley and centerfielder Mookie Betts emerging as stars, Castillo’s opportunities with the Red Sox appear to be limited. As things stand, he’s a the definition of a replacement player.

Olivera, meanwhile, is 31 and just received an 82-game suspension for a domestic violence violation. That effectively reduced his contract by almost $1.8 million, and with the Dodgers having paid his $28 million signing bonus and most of his 2015 salary, the Braves now owe him only slightly more than $30 million for the next four seasons after this one. That would seem to reduce their need to give him unlimited chances to stick in the major leagues—something it wasn’t clear he was going to do even before his suspension.

Of these three, the 25-year-old Tomas would appear to have the best chance to change his fortunes going forward. He has gotten the most major league exposure, however, and has yet to prove he’s a viable everyday player at the major league level. Tomas did get off to a good start this season, hitting .318/.372/.536 through May 11, but he has hit just .167/.231/.250 over the last three weeks, dropping his season line down to league average. From that point, his brutal play in the field has rendered him replacement-level on the season.

With Yasiel Puig, Jose Abreu and Jorge Soler also all struggling in the early going this season, teams may be far more cautious about handing out big-money contracts to Cuban defectors in the second half of the decade than they were in the first.

Designated Hitter

Prince Fielder, Rangers
Contract: Nine years, $214 million
Accumulated bWAR: 7.1
Projected bWAR: -6.3
Dollars per marginal win: $306.5 million

When Howard signed his extension with the Phillies in 2010, I looked ahead to the upcoming contracts for some of the league’s other star first baseman and identified Fielder as a player who, like Howard, would be a risky investment because of a body type that is prone to a sharp decline in its early 30s. I dove deeper into those concerns when the Tigers inked Fielder to this contract two years later. Now here we are: Howard has been a total bust, and Fielder, who was traded to Texas after the 2013 season and turned 32 in early May, is hitting .190/.257/.292 entering Friday’s action. Correcting for his hitting-friendly ballpark, that translates to a 46 OPS+. As a designated hitter, that has made him worth 1.3 wins less than a replacement-level player on the season. Two years ago, Fielder was also in the red, struggling to maintain a league-average batting line until a herniated disc in his neck ended his season in mid-May. Going forward, there’s not much reason to expect him to be a positive contributor to the Rangers.

I actually tweaked my math slightly in Fielder’s favor to arrive at the above numbers. Rather than pro-rating his -1.3 bWAR over a full season, only a third of which has elapsed thus far, I simply doubled it, assuming that if he does sink to -2.6 bWAR on the season, the Rangers will stop putting his name in the lineup. I then used that figure for my 5/4/3 projection for 2017, which, even with his 1.9 bWAR from last year, fell in the red at -0.5 bWAR. Projecting decline from there gives us the ugly numbers above and the prospect that Fielder could net less than a full win above replacement over the full nine-year term his contract. Maybe things won’t get quite that bad, but even if they don’t, there’s not a DH in the AL with a worse contract—not Alex Rodriguez, not Albert Pujols, not Victor Martinez and certainly not Billy Butler, whose entire contract is just $6 million more than Fielder’s salary for this year alone.

Starting Pitcher

Matt Harrison, Phillies
Contract: $55 million, five years
Accumulated bWAR: -0.3
Projected bWAR: 0.0
Dollars per marginal win: Sunk cost

Having been shut down with further back problems before reporting to camp this year, Harrison, who had spinal fusion surgery in 2014, seems unlikely ever to pitch in the majors again. As it stands, he has made just nine starts since signing this contract in January 2013, going 2–5 with a 6.14 ERA. Sent to the Phillies by the Rangers to offset the price of Cole Hamels's contract in last July’s deadline deal, he has yet to appear in a game for Philadelphia in the regular season or spring training.

With his deal set to expire next year, one just hopes that Harrison—who has also had to deal with thoracic outlet syndrome (twice), kidney stones and hypothyroidism during his career—can enjoy a healthier existence after baseball.