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Baseball's worst long-term contracts

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Major League front offices don't always make smart decisions, and sometimes, they give out contracts that end up looking very bad in hindsight. Here's a look at some of the worst contracts in baseball.

Isaiah J. Downing-USA TODAY Sports

MLB teams give out multi-million dollar contracts on a fairly regular basis, and it is a given that some of these contracts will work out better than others. What I will attempt to do in my next two articles is look at the absolute best and worst long-term contracts in Major League Baseball.

I am arbitrarily defining "long-term contracts" as contracts that have at least four guaranteed (non-option) years. In my analysis, I will be analyzing contracts in their entirety. This means that I will look at how players have performed relative to their contract so far, as well as how they are expected to perform going forward. I will only be looking at current contracts for players that are still in the major leagues.

For each player listed, I have included data from Cot's Baseball Contracts, including contract terms (number of years and overall dollar figure), the years the contract encompasses, earnings to-date (ETD), value to-date (VTD), surplus/deficit value, and money still owed.

The player's earnings to-date is the amount of money the player has received so far on his current contract. This figure includes one-third of the player's 2015 salary. The player's value-to-date is based on FanGraphs dollar values, which multiplies their WAR by the market value of a win on the free agent market. The surplus/deficit value is simply the player's value minus his earnings. All dollar figures are in millions.

This week, I will be covering the worst long-term contracts in baseball. While I did end up ranking these contracts, please don't see these rankings as set in stone. I could have very easily ranked some of these contracts differently, depending on how I feel about how a particular player will perform going forward. The point is that there are a lot of bad contracts in baseball, and the ones listed below are some of the worst of the worst.

1. Ryan Howard, Philadelphia Phillies

Player Contract Years ETD VTD Surplus/Deficit Money Owed
Ryan Howard 5/125 2012-2016 $73.3 -$2.8 -$76.1 $51.7

The Ryan Howard contract looked bad when it was signed, as Howard was coming off 1.0 and 1.6 win seasons in 2010 and 2011. Over the life of his contract, Howard has been slightly below replacement level, costing the team approximately $2.8 million, in addition to the $73.3 million he's been paid already. While Howard has had a small turnaround so far in 2015, he hasn't come close to justifying his $25 million salary. He is nearly untradeable at this point, unless the Phillies are willing to eat close to his entire contract.

2. Alex Rodriguez, New York Yankees

Player Contract Years ETD VTD Surplus/Deficit Money Owed
Alex Rodriguez 10/275 2008-2017 $211.0 $143.7 -$67.3 $64.0

Were it not for his excellent start to the 2015 season, A-Rod may have been at the top of this list. The Yankees have lost nearly $70 million on A-Rod's contract so far, and they still have to pay him another $64 million through 2017, not including any bonuses he may receive for moving up the all-time home run leaderboard. Unlike Howard, though, A-Rod has been capable of producing above replacement level when healthy (and not suspended). While the Yankees have plenty of reasons to regret this contract, it doesn't look as terrible going forward as some of the other contracts on this list.

3. Melvin Upton Jr., Atlanta Braves/San Diego Padres

Player Contract Years ETD VTD Surplus/Deficit Money Owed
Melvin Upton Jr. 5/75.3 2013-2017 $30.7 -$2.3 -$33.0 $44.6

Like Ryan Howard, Melvin Upton Jr. (formerly B.J. Upton) has been below replacement level over the life of his contract. In his time with the Braves, his offensive performance has plummeted, as his wRC+ went from 108 in 2012 with the Rays to 55 in 2013 and 74 in 2014. He has yet to play in 2015 due to a toe injury, and he doesn't figure to be much more than a part-time player for the Padres once he returns. Upton is still only 30, so he has time to turn things around, but given how terrible his last two years have been, it is still hard to see him being significantly better than replacement level going forward.

4. Matt Kemp, Los Angeles Dodgers/San Diego Padres

Player Contract Years ETD VTD Surplus/Deficit Money Owed
Matt Kemp 8/160 2012-2019 $60.0 $23.8 -$36.2 $100.0

The Dodgers gave Kemp an extension after his career year in 2011, and since then, he has not been able to come close to his 2011 level of performance. Kemp has dealt with a myriad of injuries, and his defensive performance has suffered greatly, taking away much of the value he provides on offense. He has already been severely overpaid relative to his performance so far, which is never a good sign when looking at the front end of a long-term contract. The Dodgers' decision to trade Kemp and shed most of his remaining salary looks great in hindsight, as he is off to a very slow start in San Diego so far this season.

5. Carl Crawford, Boston Red Sox/Los Angeles Dodgers

Player Contract Years ETD VTD Surplus/Deficit Money Owed
Carl Crawford 7/142 2011-2017 $86.6 $42.5 -$44.1 $55.4

Crawford had a terrible two years with the Red Sox, but since being traded, he has been a serviceable regular in left field for the Dodgers. Still, he has not come close to justifying his contract, and this deal will only look worse as Crawford ages. However, if there's one team that can absorb a bad contract, it is the Dodgers, who managed to make the playoffs two years in a row with both Crawford and Kemp on their roster.

6. Josh Hamilton, Los Angeles Angels/Texas Rangers

Player Contract Years ETD VTD Surplus/Deficit Money Owed
Josh Hamilton 5/125 2013-2017 $37.7 $25.7 -$12.0 $87.7

Given everything Arte Moreno did in his attempt to get out of Josh Hamilton's contract, it is no surprise that this deal ranks as one of the worst in all of baseball. While Hamilton's deficit value of $12 million may seem small compared to other players on this list, it is important to keep in mind that Hamilton's deal is very backloaded. He is still owed nearly $90 million over the next three years, and the Angels will be paying most of this while Hamilton tries to resurrect his career with the Rangers.

7. Albert Pujols, Los Angeles Angels

Player Contract Years ETD VTD Surplus/Deficit Money Owed
Albert Pujols 10/240 2012-2021 $59.0 $57.7 -$1.3 $181.0

While Pujols has produced value comparable to what he has been paid so far, this deal will almost certainly end much worse for the Angels. For this deal to end well for the Angels, Pujols would have needed to produce a high surplus value at the beginning of his contract to make up for a drop in performance in his decline years. Pujols isn't higher on this list because he is only in the fourth year of his contract and is producing offensively for the Angels. This deal is significantly backloaded and will probably look much worse in a few years, which is why it still makes the top ten on this list.

8. Shin-Soo Choo, Texas Rangers

Player Contract Years ETD VTD Surplus/Deficit Money Owed
Shin-Soo Choo 7/130 2014-2020 $18.7 $3.6 -$15.1 $111.3

Choo has struggled mightily in his first year plus with the Rangers, in part because of injuries. He has barely been above replacement level and is still owed over $100 million through 2020. He isn't too far removed from being a five-win player for the Reds, though, so there is a chance he could turn things around. Amidst all his struggles, he has been slightly above average on offense with the Rangers, so perhaps he would do better as a full-time DH. Even so, it would be miraculous if Choo ends up coming close to producing enough to justify his contract.

9. Nick Swisher, Cleveland Indians

Player Contract Years ETD VTD Surplus/Deficit Money Owed
Nick Swisher 4/56 2013-2016 $31.0 $2.7 -$28.3 $25.0

Swisher had a solid but unspectacular year with Cleveland in 2013 before falling off a cliff in 2014. In total, he was 1.6 wins below replacement level in just 401 plate appearances. His season ended early when he underwent arthroscopic surgery on both knees, and so far in 2015, he has continued his poor level of play. At this point, it is conceivable that the Indians could end up paying Swisher $56 million and get next to nothing in return. At this point, the only saving grace for the Indians is that they didn't give Swisher more than four years.

10. CC Sabathia, New York Yankees

Player Contract Years ETD VTD Surplus/Deficit Money Owed
CC Sabathia 5/122 2012-2016 $76.7 $55.5 -$21.2 $45.3

Sabathia had a great start to his Yankee career, accumulating 17.4 fWAR through his first three years with the team. After he opted out of the rest of his contract, the Yankees made the mistake of giving him yet another big contract to remain with the team. He missed almost all of 2014 with a recurring knee injury, and he has been unspectacular in just over 60 innings so far this season. While his peripherals suggest that he could be a solid back-end starter, the Yankees are clearly paying him to be much more than that. Sabathia is set to turn 35 next month, and at this point in his career, it is hard to see him getting any better than he is right now.

Just Missed

Elvis Andrus, Texas Rangers

Player Contract Years ETD VTD Surplus/Deficit Money Owed
Elvis Andrus 8/120 2015-2022 $5.0 -$3.4 -$8.4 $115.0

Justin Verlander, Detroit Tigers

Player Contract Years ETD VTD Surplus/Deficit Money Owed
Justin Verlander 7/180 2013-2019 $49.3 $56.4 $7.1 $130.7

Matt Cain, San Francisco Giants

Player Contract Years ETD VTD Surplus/Deficit Money Owed
Matt Cain 6/127.5 2012-2017 $61.7 $37.0 -$24.7 $65.8

Prince Fielder, Texas Rangers

Player Contract Years ETD VTD Surplus/Deficit Money Owed
Prince Fielder 9/214 2012-2020 $78.0 $58.1 -$19.9 $136.0

Matt Harrison, Texas Rangers

Player Contract Years ETD VTD Surplus/Deficit Money Owed
Matt Harrison 5/55 2013-2017 $17.3 -$0.1 -$17.4 $37.7

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Nick Lampe is a contributor at Beyond the Box Score and Viva el Birdos. You can follow him on Twitter at @NickLampe1.