Like all good CEOs, the men who run Major League Baseball’s 30 teams try to be forward-thinking. Even those who have only the most cursory interest in number-crunching understand that baseball players typically peak in their twenties and decline in their thirties. They’re fully aware of the pitfalls of awarding a fat, long-term contract to an aging, one-dimensional slugger or pretty much any pitcher.

Yet they routinely ignore those well-established risks. Sometimes they do so because they’re easily seduced by star power; other times because they have more money than they can hope to spend; and still other times ebecause the owner says he wants to win a World Series before he dies, and thinks this free agent is the one to help him do it.

And, for the third year running, those misguided decisions have given rise to Grantland’s annual look at baseball’s most ignominious contracts. (Here are the first and second lists.) Before the winter meetings, we ranked the game’s 50 most valuable trade commodities, and now it’s time to consider the opposite: the players with contracts so burdensome no team would willingly take them on. Remember, the players on this list aren’t bad; some of them are still skilled guys who could be assets on the right team. But they’re all getting paid far more than they’re worth now or will be worth in the near future, meaning they’d generate little to no interest if they hit the trading block tomorrow.

A Worst Contract Rules Refresher

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1. Obviously, contracts matter. Per FanGraphs, Albert Pujols and Carlos Santana were both worth a shade more than three Wins Above Replacement in 2014. We can debate the merits of WAR, but we can’t debate that the Indians got the better value: They paid Santana $3.5 million last year, while the Angels paid Pujols $23 million in 2014 and still owe him a total of $189 million (plus incentives) over the next seven seasons.

2. Team finances matter, but only so much. A big-budget club like the Dodgers can survive poor production from a player making $10 million, $15 million, or even $20 million a year, because it has nearly unlimited money to spend plugging roster holes. A low-budget team like the Pirates, on the other hand, can suffer mightily from one really bad contract. For the purposes of this column, however, I’m acknowledging that gap while arguing that a bad deal is still a bad deal.

3. An expensive contract is not automatically undesirable. This season, Mike Trout will enter the first year of his six-year, $144.5 million contract. Since Trout is just 23 years old and is already the best player in baseball, that dollar total is cause for celebration, not lamentation.

4. We’re excluding generic replacement-level players. No team is going to offer much for Skip Schumaker, and clubs can cut players of that ilk with little or no financial repercussions. For a player to have negative trade value and thus one of baseball’s worst contracts, he needs to be a major financial burden to his current team and unattractive to the rest of the league.

5. Deferred contracts don’t count. Some players who are no longer in the majors will collect big chunks of change from their former employers in 2015. Bobby Bonilla, for example, will be getting money from the Mets until the sun explodes. I’m not considering those guys or players who are still getting paid even though they’re no longer on MLB rosters but haven’t officially retired.

6. Guarantees only. We’re factoring in only the money these players will definitely see. Club-option years don’t count, since none of these players figure to be good enough to justify the totals they’d stand to make in their option years.

Dishonorable Mentions

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DH Nick Swisher, Cleveland Indians: two years, $30 million remaining

OF Michael Bourn, Cleveland Indians: two years, $27.5 million

When the Indians signed Bourn and Swisher, I praised the team for spending real money on free agents to augment its core of promising young players. The Bourn deal in particular looked like a coup: The speedy center fielder had sought a $75 million free-agent deal, but by waiting out the market until February, the Tribe landed the All-Star for considerably less, doling out $48 million over four years instead.

Neither deal has worked out, however. Bourn was a replacement-level player last year, while Swisher was even worse than that, pulling off the trifecta of hitting just above the Mendoza Line, playing lousy defense, and getting hurt. And while I try not to weigh team finances too heavily when analyzing these contracts, I can’t discount that the Swisher and Bourn albatrosses will hurt the small-revenue Indians more than they would nearly any other team. As one AL executive put it:

“These might not seem like killers, but how much better off are the Indians the next two years with their young core and [nearly] $30 million a year to supplement what they currently have on the free-agent market? Imagine the current Indians team with Andrew Miller and James Shields. It sucks to be a small-market team sometimes.”

SP Edwin Jackson, Chicago Cubs: two years, $22 million

Among pitchers with at least 140 innings, Jackson’s 6.33 ERA was the worst in baseball last year by nearly a full run. With Jon Lester and Jason Hammel now in the fold, Jackson isn’t even ticketed for the rotation anymore. That means he’s either going to be a mop-up man in 2015 or on the chopping block in spring training.

SS Elvis Andrus, Texas Rangers: eight years, $120 million

Assessing a player’s value requires considering a complex mix of scouting, statistical analysis, health analysis, age curve assessment, and about 100 other factors. In Andrus’s case, the equation turned out to be much simpler: If Scott Boras, who’s known for discouraging his clients from signing long-term extensions before testing the free-agent market, tells a client to take an extension, then that deal is probably a huge win for the player and a huge mistake for the team.

Andrus signed his extension in April 2013, just as that season was beginning, and he did so two seasons before he’d have been able to test the open market. But the real kicker here is that the new deal hasn’t even begun yet; it actually starts two months from now, when he’ll make $15 million for the 2015 season. That’s a hell of a lot of money for a player who has slugged a combined .332 over the past two seasons while playing in the American League’s best hitter’s park. He’s still only 26 years old, and he plays good defense, but we now have six years of major league evidence that he can’t hit (his .272/.335/.345 career line is 16 percent below league average after adjusting for Arlington’s confines), and his defense isn’t nearly at the Andrelton Simmonsesque elite level it’d need to reach to justify spending so much money for so little offense.

Aside from the Boras lesson, the main takeaway here is one that we’ll repeat several times throughout this column: When dealing with players who are still under team control for a couple more years, clubs should tread very carefully before offering an extension that won’t kick in until those years have expired. The consequences of failing to exercise that care can be disastrous.

SP Bronson Arroyo, Arizona Diamondbacks: one year, $14 million

Technically, Arroyo’s remaining deal is $9.5 million for 2015 plus a $4.5 million buyout to avoid his $11 million salary in 2016. Either way, the result is the same: Arroyo had Tommy John surgery in early July, making him a long shot to return before August and a virtual lock to deliver nothing of value for a moderate-payroll club that’s also overpaying Cody Ross and Trevor Cahill to not contribute.

OF Carlos Beltran, New York Yankees: two years, $30 million

1B Mark Teixeira, New York Yankees: two years, $45 million

SP CC Sabathia, New York Yankees: two years, $53 million

The Yankees have been throwing big bucks at aging stars since before any of these guys were born; sometimes that strategy landed them a guy like Reggie Jackson, other times players whose final years in New York are exceedingly ugly.

Of these three, Sabathia’s ending could be the ugliest. He tossed just 46 innings last season, the first time since 2006 that he’d failed to log 200-plus innings. He’s reportedly been back to 100 percent for a while after undergoing knee surgery in July, which sets up a weird catch-22: On the one hand, the Yankees obviously could use innings from the veteran lefty, even if he’s no longer anything close to the team’s ace; on the other hand, his $25 million option vests in 2017 as long as he doesn’t end the 2016 campaign on the disabled list, spend more than 45 days on the DL, or make more than six relief appearances, all as a result of a shoulder injury. Given that Sabathia will be 36 years old in 2017 and has some ugly trends on his résumé — his ERAs the past four seasons: 3.00, 3.38, 4.78, 5.28 — seeing him in pinstripes three years from now wouldn’t necessarily be a great outcome for the Yankees.

SP Ubaldo Jimenez, Baltimore Orioles: three years, $38.75 million

Oy.

1B Joey Votto, Cincinnati Reds: nine years, $213 million

Votto signed his gigantic contract in April 2012, and in the two years since, I’ve agonized over whether to include him in my annual look at baseball’s best contracts; I left him off both times and got enough hate mail from Votto supporters to fill an Olympic-size swimming pool. And understandably so: From 2010 through 2013, Votto was around a six-win player every year, and an MVP award winner in 2010.

How quickly things can change. In 2014, he missed 100 games and hit for less power than ever before. It’s human nature to fixate on the recent past, and it’s pretty terrifying to see a 31-year-old player who’s owed $213 million after a season in which he hit .255 with six home runs — terrifying enough to make four years of absolute dominance seem like a distant memory.

But while it’s possible that the combination of Votto’s age, nasty 2014 quad injuries, passive hitting approach, and massive contract will make him a major impediment to the Reds’ success for years to come, it’s important that we maintain some sense of context. One season doesn’t make a trend, and we’ve got years of evidence to suggest that as long as Votto is healthy, he’s Wade Boggs with power, the kind of hitter who comes along maybe a few times each generation.

Given the Reds’ limited revenue stream, the Votto risk factors we can’t ignore, and the sheer enormity of this contract, though, there’s enough here to cause concern. Several of the talent evaluators I consulted for this story spoke harshly about the $213 million left on Votto’s deal, with two assistant GMs calling the contract one of the five worst in baseball. I’m not quite ready to lump Votto in with baseball’s five (or 10) biggest sinkholes, but I also can’t ignore the very real possibility that this deal ends terribly for Cincinnati.

The Miguel Cabrera Consideration

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1B Miguel Cabrera, Detroit Tigers: nine years, $270 million

Here’s what I wrote about Cabrera’s $248 million extension last March:

Detroit would have been fully justified in signing its franchise player to a lucrative extension once his current deal had concluded. But that time hadn’t arrived. Not even close. In handing Cabrera this extension now, the Tigers are channeling the Phillies circa April 2010. Back then, Philly gave Ryan Howard a five-year, $125 million extension. Like Cabrera, Howard didn’t offer much in the way of defensive or baserunning contributions, but he was an elite hitter and a durable player, and that’s what the Phillies wanted to lock up. The problem is, they did so nearly two years before Howard would’ve become a free agent, committing to a player through the meat of his 30s much earlier than they needed to. The results have been disastrous. Howard’s injuries started piling up, and his numbers started going down. Now, instead of each spring in Philadelphia bringing new hope, it brings another excuse to check the Howard contract countdown, which still has three years and $85 million remaining before the team will be free of the financial prison in which it foolishly placed itself. The Tigers are probably in store for a similar fate. It may seem like a reach now, given his consistent excellence and generally consistent health (he did battle a groin injury during the 2013 playoffs that ultimately required surgery), but something will happen to Cabrera, just like something happened to Howard, because they’re both human beings in addition to baseball players, and this is the kind of stuff that happens as people age.

Well, we can now scratch the “durable” tag off Cabrera’s résumé: Miggy is recovering from October ankle surgery and may not be ready for Opening Day. He’s also coming off a season in which he posted his lowest home run total since his rookie season; his lowest walk rate and batting average in six years; and his worst overall season by park- and league-adjusted offense in five years (per wRC+).

Even with all those black marks, Cabrera was still the 10th-best hitter in the majors in 2014, but he’ll turn 32 just after Opening Day, and the Tigers are now bound to him through his 40th birthday.

Cabrera isn’t in the bottom 10 here because a team with vast resources like the Dodgers would still trade for him in a heartbeat if he became available, knowing he remains a force at the plate even if he’s down a tick from his peak. But there’s a good chance this contract will become downright terrifying in a few years, particularly since it doesn’t actually begin until 2016. Father Time will forever remain undefeated.

The 10 Worst Contracts

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(Last year’s ranking appears in parentheses.)

10. SP Justin Verlander, Detroit Tigers: five years, $140 million (not ranked)

The Tigers are in full “NOTHING TO SEE HERE, MOVE ALONG” mode with Verlander, chalking up the worst season (by Baseball-Reference’s WAR) of their longtime ace’s career to his January 2014 abdominal surgery. Dave Dombrowski apparently believes the righty has been Hot Tub Time Machine’d back to 2012. “Justin Verlander is as prime a pitcher as there is in the game of baseball,” Detroit’s GM recently told a reporter, presumably as a smirking Rob Corddry looked on.

Unfortunately for the Tigers, the numbers don’t support Dombrowski’s claim, with Verlander’s velocity dipping well before his 2014 surgery.

Year Four-seam Change Slider Curve 2007 94.93 82.80 0.00 80.63 2008 94.63 84.60 85.81 81.77 2009 96.36 84.63 88.52 80.80 2010 96.12 86.56 87.86 80.18 2011 95.75 87.18 86.33 80.15 2012 95.18 86.41 85.12 80.17 2013 94.46 85.02 87.08 80.03 2014 93.39 84.45 86.48 80.09

(Velocity data courtesy of Brooks Baseball.)

That’s … not encouraging. While 2014 marked a big step down, the subtle signs of skills erosion were visible in 2013, too, with Verlander posting his worst ERA and defense-independent results in half a decade.

On the one hand, if Verlander can bounce back from his ugly 2014 effort — when his strikeout rate plunged to 17.8 percent from 23.5 percent the previous year — and return to his prior form, he will still be one of the better starting pitchers in the league, even if he’s not quite the Cy Young– and MVP-winning Verlander of old.

On the other hand, injuries and decline aren’t anomalous for pitchers who’ve logged as many innings over as many years as Verlander has. With overpaid, aging stars, baseball’s worst farm system, and an octogenarian owner who desperately wants a ring and doesn’t give a damn about mortgaging the future to try to get one, the Tigers could be a couple of years away from becoming the new Phillies.

9. OF Andre Ethier, Los Angeles Dodgers: three years, $56 million (dishonorable mention)

Ethier was a good hitter when the Dodgers dropped a five-year contract into his lap in June 2012, but he wasn’t particularly good at anything else, making the extension a puzzler at the time, and a decision that has looked worse with each passing day. Because this is the Dodgers and not the Royals or Rays, this contract hasn’t crippled the team’s finances. But the problem is that even big-revenue, well-run clubs feel compelled to play the guy with the big contract, and even those clubs can become reluctant to spend more money to find someone better.

Luckily for the Dodgers, Yasiel Puig turned into a star and Joc Pederson matured into an exciting prospect who could open some eyes if he wins the starting center-field job this spring as expected. So instead of being a total anchor, Ethier will merely wind up being a fourth outfielder making $18 million a year and offering zero trade value.

8. OF Josh Hamilton, Los Angeles Angels: three years, $83 million (6)

Hamilton typifies the kind of player on this list: a former superstar who got paid an unholy amount of money and is now declining in his thirties. He turns 34 in May, he’s coming off a season in which he missed 73 games, and suddenly he may not be ready for Opening Day after February 4 surgery on the AC joint in his right shoulder. His free-swinging approach combined with his increasingly slow reaction time and teams’ decreasing willingness to throw him the pitches he likes means it could get worse from here.

Optimists can hang their hats on two factors: (1) Hamilton cranked 43 homers as recently as 2012, so the power’s not gone, and (2) the Angels have to pay him for only three more years, so if his once off-the-charts talent fails to consistently return, at least he won’t clog the payroll for nearly as long as the other Angel in this bottom 10.

7. 1B Ryan Howard, Philadelphia Phillies: two years, $60 million (3)

Howard is the original cautionary tale against extending star players two years before free agency, and his contract has been a source of near-universal mockery since the day it was announced. Putting the 35-year-old former MVP up for sale is the right move for the Phillies, but it’s doubtful any team would want Howard, even if the Phils paid the bulk of his freight. At this point in his career, even calling Howard a platoon DH is probably pushing it: His numbers over the last three years look startlingly similar to Luke Scott’s, and Scott had to go to Korea to find a job.

6. 1B Albert Pujols, Los Angeles Angels: seven years, $189 million (2)

It’s worth debating whether there’s more value in a player like Howard, who has pretty much zero meaningful impact at this stage of his career but will only haunt Phillies accountants for two more seasons, or a player like Pujols, who still contributes but is nowhere near the talent he used to be and is on the books for seven more seasons. Let’s hear what a couple of high-ranking baseball ops folks think:

“I think that the contracts where you’re essentially getting zero production or, even worse, you’re better off just dumping the guy rather than letting him hurt your team are the worst, regardless of money owed. Mauer and Votto and Cabrera are overpaid/well above their market value, but if you take the money out of the equation, at least you’re not making your team worse by having them. [B.J.] Upton, Ethier, and Howard, on the other hand, are complete sinkholes.”

Counterpoint: “I feel like the longer the deal, the more risk. Like with Upton or even A-Rod — it’s over in three years. I think the worst contract in the game, far and away, is Pujols.”

This is a matter of both general philosophy and specific prognostication. If you’d rather have Pujols for all those years and all that money, you’re banking on his next few seasons approaching something like his 2014 campaign, when he missed just three games, smacked 28 homers, and posted an overall park-adjusted line 24 points better than league average per wRC+, a strong rebound from an ugly, injury-plagued 2013. That production still made him overpriced, but at least the 2014 Pujols wasn’t a total dead weight like Howard or Alex Rodriguez. If, however, you’d rather bite the bullet on two or three years of borderline-nonexistent production from a player earning $20 million to $30 million a season, you’re probably pretty damn pessimistic about the 35-year-old Pujols’s usefulness over the next seven years.

Both arguments are defensible. And considering the baseball colossus that Pujols once was, they’re also both kind of sad.

5. 1B Prince Fielder, Texas Rangers: six years, $144 million (14)

This deal isn’t quite as bad as it initially seems for the Rangers, because the Tigers are covering $30 million of what Fielder is owed. It’s still pretty bad, though. Fielder played just 42 games in his first season in Texas, and though he’s reportedly pain free and “ready to go” for spring training, we can’t just dismiss the neck injury that cost him all that time. Even at his healthy peak, Fielder couldn’t run, field, or do anything other than hit, and his numbers had already begun to slip in 2013, before he got traded or hurt. If his neck problems persist or another injury surfaces, this could quickly become the worst contract in baseball.

4. OF Shin-Soo Choo, Texas Rangers: six years, $116 million (NR)

Here’s another over-30 Ranger coming off an injury-plagued season who’s signed for waaaay too long and waaaay too much. Though Choo missed just 39 games last year, he first hurt his ankle back in April, so it’s possible a season-long mulligan is warranted. Maybe his .242/.340/.374 face-plant was a big aberration, and more .400 OBP seasons and piles of doubles are on the way.

Coming off lost seasons, Fielder and Choo possess enough upside to make Texas a real sleeper in 2015. But if 2014 was the new normal, Rangers fans should try not to think about 2016 and beyond.

3. CF B.J. Upton, Atlanta Braves: three years, $46.4 million (5)

As the top three names on this list suggest, I believe it’s better to have a good but overpaid player than someone with no discernible value. Upton is still just 30 years old, so in theory he could reclaim some of his former value, but let’s be realistic here: He has batted .198 over the past two years, with 324 strikeouts in 910 at-bats. His swing is broken, the flashes of power he once showed are now exceedingly rare, and even his speed — the one element of his game that was always there when he posted solid but inconsistent results in Tampa Bay — isn’t anywhere near the weapon it used to be.

If Upton weren’t owed all this money, what would his role with the Braves be? Fourth outfielder? Fifth outfielder? If things don’t improve soon, the most likely outcome is that he’ll receive the Dan Uggla treatment.

2. SP Matt Harrison, Texas Rangers: three years, $41 million (NR)

When the Rangers gave Harrison his five-year, $55 million deal in January 2013, they were rewarding a 27-year-old durable ground ball pitcher who’d managed the rare feat of putting up solid numbers in the AL’s worst pitcher’s park, in the process buying out three years of arbitration and two years of free agency. Even though Harrison was never a big strikeout pitcher by the standards of the time, the contract didn’t seem like much of a reach.

But now here we are, with Harrison having made just six combined starts in the past two seasons and coming off spinal fusion surgery. It’s unclear if he’ll ever pitch again in the majors, let alone take the ball every fifth day and produce quality numbers. From their Game 6 World Series collapse to the wave of injuries and bad contracts now on their books, the Rangers are as snakebitten as any team with a $3 billion TV deal could possibly be.

1. 3B Alex Rodriguez, New York Yankees: three years, $61 million (1)

The king stay the king, with A-Rod claiming this spot for the third year in a row. Not that his reign should be any surprise. Rodriguez will turn 40 this year, his hips might be shot for good, he’s coming off a 162-game PED suspension that could’ve been a lifetime ban, and he’s got self-righteous sportswriters so worked up that one compared him to a mob boss/serial killer.

You know what, though? I’m still pulling for him. Despite all of his mistakes, and despite the Yankees signing Chase Headley to a lucrative four-year deal, Rodriguez still has the unshakable confidence to believe the third-base job is his to lose. By all accounts, he’s been working his ass off to get back into game shape. He needs six more homers to reach 660 for his career, which would trigger a $6 million bonus clause in his contract and cause a damn riot on talk radio. He has certainly caused his own problems, and he deserves to pay the price for his mistakes.

But there would be something poetic about seeing Rodriguez recapture his old form, even if just for a month, or a week, or a couple of at-bats. Like everyone else on this list, A-Rod is here because he was once great — in his case one of the 15 or 20 best players to ever wear an MLB uniform. We watch the games because that kind of greatness is a joy to behold, and because we’re all eventually headed for old age and obsolete status no matter what we do for a living.

So, yes, I’m rooting for the bad guy. Seeing A-Rod force all the doubters to eat crow would make a lot of people angry, but man, what a story that’d be.