Bad deals are inescapable in sports and pop culture. Endless, exorbitant, ridiculous contracts can destroy a team’s future, ensnare a rising young star, or cripple a major studio. Also, they’re hilarious. In honor of these horrible agreements, we present a look at some of the most egregious in their respective fields. Welcome to Worst Contracts Week.

Earlier this offseason, I highlighted baseball’s most valuable trade commodities. Now it’s time for the ugly bookend: the players few teams would dream of touching. Welcome to Grantland’s second-annual look at baseball’s 15 worst contracts.

Remember, the players on this list aren’t necessarily bad; some of them are still quite good and would be useful assets on many teams. But they carry crippling contracts, meaning they’d generate little to no interest if they became available via trade tomorrow.

So refresh your memory with a rundown of the Worst Contract Rules, and then brace yourself for the wave of terror this year’s top 15 will bring.

Worst Contract Rules

1. Contracts matter. Per FanGraphs, Adrian Gonzalez and James Loney were both worth a shade fewer than three Wins Above Replacement in 2013, and they posted similar batting averages, on-base percentages, and other more traditional stats. We can debate the merits of WAR, but we can’t debate that the Rays got the better value: They paid Loney a base salary of $2 million last year, while the Dodgers paid Gonzalez $21 million in 2013 and still owe him another $106 million over the next five 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. Miguel Cabrera is entering the seventh season of his $152.3 million deal, and will make $22 million in each of the next two years. That’s a lot of money, but it wouldn’t keep teams away. Any club would kill for the privilege of paying Cabrera $44 million for two seasons of service.

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

5. Deferred contracts don’t count. Some players no longer in the majors will collect big chunks of change from their former employers in 2014. Bobby Bonilla, for example, will be getting money from the Mets until the sun explodes. I’m not considering those guys, nor players like Vernon Wells, who are no longer on MLB rosters even though they’re still getting paid.

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

• SP Josh Beckett, Los Angeles Dodgers: one year, $15.75 million remaining

• OF/DH Adam Dunn, Chicago White Sox: one year, $15 million

• 2B Rickie Weeks, Milwaukee Brewers: one year, $12 million

• SS Jose Reyes, Toronto Blue Jays: four years, $86 million

• OF Andre Ethier, Los Angeles Dodgers: four years, $71.5 million

• RP Jonathan Papelbon, Philadelphia Phillies: two years, $26 million

• RP Rafael Soriano, Washington Nationals: one year, $21 million

The 15 Worst Contracts

15. 1B Adrian Gonzalez, Los Angeles Dodgers: five years, $106 million remaining (last year’s rank: 14)

14. 1B Prince Fielder, Texas Rangers: seven years, $168 million ($30 million paid by Tigers) (NR)

Gonzalez and Fielder are currently slightly above-average players being compensated like superstars, and things will only get worse from here.

Gonzalez turns 32 in May, and between his advancing age and the shoulder injuries that have plagued him in the past, it’s now extremely unlikely he’ll hit 40 homers again; in fact, 30 might be a stretch. In addition to no longer delivering the kind of power that teams want out of a first baseman, Gonzalez doesn’t walk anymore and will see his bat speed decline over the next five years. Plus, his already poor baserunning and defense will decline further.

Fielder, meanwhile, is even more limited when he’s not hitting 35-40 homers. To wit:

Fielder is also an unusual case. He doesn’t turn 30 until May, and he’s heading to a ballpark that could revive his power numbers. But most crucially, he actually was traded this winter. While the Tigers got a solid second baseman in Ian Kinsler in exchange, though, they had to throw a giant gob of money at the Rangers to complete the deal.

The biggest reason these two first basemen are on this list is because they’re going to be costing their teams huge sums well into their mid-thirties. While wealthy teams like the Rangers and Dodgers might not care as much about sunk costs as their small-market brethren do (that the Dodgers are considered NL West favorites despite having so many players on this list speaks volumes), playing time is the great equalizer.

It’s not just that Gonzalez and Fielder will make $20 million–plus as 35-year-olds. It’s that even the richest teams can’t simply bench or release a Gonzalez or a Fielder at that stage in favor of a better, younger first baseman. Those guys have to play, and that can mean spending big on a player who’s essentially just standing in the way of younger, cheaper talent. The Curse of Plenty didn’t end up hurting the Dodgers in 2013, but it likely will at some point down the road. In a baseball landscape where national TV money is washing over every team, and a fortunate few are parlaying lucrative local TV deals into net worth the size of small countries, this playing time quandary will be the toughest to overcome.

13. 2B Dan Uggla, Atlanta Braves: two years, $26 million (NR)

These rankings are subject to change based on year-to-year performance. Jayson Werth was on this list a year ago, for example, but a big 2013 campaign made his huge contract look more reasonable. While the same could prove true for Uggla, for now he’s stuck in a continuing decline.

It began in 2012, when he hit .220 with 19 homers after five consecutive seasons with 30 or more bombs. Last season was considerably uglier, though, with Uggla’s .179 batting average tying for the lowest among qualified hitters in the past century. In the past, Uggla has been able to provide ample value despite a poor batting average thanks to his walks and especially thanks to the power he provided at second base. However, if he’s parking just 20 a year while also bringing poor foot speed, iffy defense, a strikeout in every three at-bats, and flirtations with the Mendoza Line, he’s worth far, far less than the $13 million he’s getting per season, and really has no business starting for a team with legitimate playoff aspirations like the Braves.

12. SP Ricky Romero, Toronto Blue Jays: two years, $15.6 million (NR)

Romero might end up appearing in fewer major league games over the next two years than all but one other player on this list. The Jays would need to show a surprising amount of faith to put him back on the mound after he netted the worst ERA in the league among starters in 2012, and then followed it up with an 11.05 mark in his 7⅓-inning cameo last season.

It’s hard to say whether Romero is suffering from an injury or some kind of modern-day Steve Blass disease. Whatever it is, Romero has gone from being one of the AL’s top starters just three years ago to one of the game’s most perplexing stories. His contract didn’t keep the Jays from last offseason’s spending spree, nor will it prevent them from pursuing Ervin Santana and/or Ubaldo Jimenez the rest of this offseason. Carrying a dead-weight contract for a pitcher who’s highly unlikely to even see the mound this year still hurts, though.

11. RP Jonathan Broxton, Cincinnati Reds: two years, $17 million (NR)

10. RP Brandon League, Los Angeles Dodgers: two years, $17 million (13)

Including our dishonorable mentions, we’ve got four relief pitchers among the 21 worst contracts in baseball. Such is the danger in offering a long-term deal to any member of the position group responsible for the most volatile year-to-year results in the league.

At least a pitcher like Papelbon had displayed elite skills and results throughout his career, and hadn’t begun to suffer simultaneous drops in fastball velocity and strikeout rate until after signing his big deal. With Broxton and League, conversely, some decent ERAs and save totals have masked their underwhelming performances. Neither pitcher boasts an impressive ability to miss bats, and League brings shaky control to boot. If his 2013 numbers are what we can expect from him going forward, it’d be fair to ask if he even belongs in the big leagues, let alone if he’s worth $17 million the next two years.

With starters throwing fewer innings than ever, and relievers tossing more than ever, it stands to reason the best relievers should make more money than ever. But even top-tier closers bring considerable risk, and, simply put, Broxton and League aren’t top-tier. Both pitchers had crummy peripherals when they signed big deals, and when teams give multiyear contracts to pitchers based on save totals or ERA rather than strikeouts, walks, and home run rates, it almost always backfires.

9. OF Carl Crawford, Los Angeles Dodgers: four years, $82.5 million (2)

This deal doesn’t look nearly as bad as it did a year ago, when Crawford was coming off a disastrous season in which he played just 31 games for the Red Sox. Crawford hit .283/.329/.407 in 2013, his best offensive numbers since his final, superb season with the Rays three years earlier. He also looked better in the field than he had since his Tampa Bay days, as he was finally healthy(ish) after battling wrist, elbow, hamstring, and other injuries.

Still, this deal isn’t going to end well for the Dodgers. Crawford is already 32 years old, he’s lost some of the devastating speed that made him an elite base stealer and defender, and he’s never possessed great power or on-base skills. His health also remains an ongoing concern: While he played more than 31 games last year, he still missed 46. When Yasiel Puig burst onto the scene, it seemed that the Dodgers had a glut of outfield options. Now, depending on Matt Kemp’s health, the better read is probably that the Dodgers have Puig and three outfielders banking a fair bit more than they’re worth.

8. SP Chad Billingsley, Los Angeles Dodgers: one year, $15 million (NR)

Hey, another Dodger! Billingsley is working his way back from Tommy John surgery, but isn’t due to return until June at the earliest. But just as the Dodgers paid Ted Lilly $12 million to throw 23 ineffective innings last year, Billingsley will get $15 million to toss a limited number of possibly ineffective innings this year. Yet it won’t make a lick of difference when it comes to the Dodgers’ ability to sign checks or make a World Series run. Must be nice.

7. SP John Danks, Chicago White Sox: three years, $42.75 million (11)

Danks made this list last year, and what I said then still applies: If he can return to good health, the rest of his contract could work out fine. It’s hard not to assume the worst, though, after 2012 surgery to “repair capsule tear and rotator cuff and biceps tendon debridement,” followed by a 63-day DL stint last year for inflammation in that same surgically repaired shoulder. Danks did make 22 starts in 2013, but he posted defense-independent results that were no better than those he delivered during the tumultuous period leading up to his surgery.

Danks has gone from being one of the best pitchers in the game at age 23 to throwing what we can only hope is something better than batting-practice fodder at age 28. Pitching is a cruel profession. And the White Sox are on the hook for a considerable sum regardless of which Danks surfaces this year.

6. OF Josh Hamilton, Los Angeles Angels: four years, $99.6 million (NR)

I thought the Angels overpaid for Hamilton when they signed him prior to last season, but I still liked the deal. The iffy plate discipline was no secret, the move from hitter-friendly Arlington to pitcher-favoring Anaheim was bound to ding his numbers, and Hamilton was a near lock to regress over the course of his five-year, $125 million deal, because that’s what happens to nearly every player as he approaches his mid-thirties. Still, Hamilton’s natural talent was so immense that I figured he’d parlay his free-swinging, aim-for-the-moon approach into something like 120-150 homers over the life of the deal.

If 2013 was a proper indication, that’s not going to happen. Hamilton managed just 21 homers while slugging just 182 points better than his batting average, the worst such result since his injury-plagued 2009 season. If 20-plus homers is Hamilton’s ceiling from here on out, he’s in big trouble. His swing-at-everything mentality resulted in a .224 batting average with a .283 on-base percentage before last year’s All-Star break, and that kind of out-making coupled with merely decent power would make him bench material if he weren’t a star player with a huge contract.

Hamilton was one of the 10 best hitters in the game from 2010 through 2012, so it’s possible 2013 was an aberration and we could see him return to form in 2014. Given Hamilton’s $25 million–per-year average salary, and given the commitment the franchise has made to fellow struggling veteran Albert Pujols, the Angels had better hope so.

5. OF B.J. Upton, Atlanta Braves: four years, $59.8 million (NR)

It’s a good thing I don’t believe in omens or superstitions. Otherwise, I might note that two of the three biggest contracts in Braves history prior to this offseason went to Upton ($75.25 million in total value via free agency) and Uggla ($62 million via extension), with the sum of those two deals adding up almost exactly to the extension just awarded to newly anointed highest-paid Brave Freddie Freeman.

Like all the other players on this list, Upton is here because he once showed enough ability to warrant a big, fat contract. For Upton, “once” isn’t some remote, distant memory, either. From 2007 through 2011, he was roughly a four-win player. He struck out too much, and his power would flicker on and off, but he was a strong all-around player, one of the scariest base stealers and baserunners in the game, and a smooth, gliding center fielder who played abnormally shallow thanks to his ability to race back and turn potential doubles and triples into outs.

In 2013, his first year with the Braves, Upton was one of the worst everyday players in the majors, with all of his weaknesses and none of his strengths coming to the fore. He whiffed in one-third of his at-bats, hit a horrendous .184 with a brutal .268 on-base percentage, and played himself out of the lineup for the division-winning Braves. Upton’s just 29 years old, he’s lithe and durable, and he still looks the part of a multi-tooled star. He’s on this list because he has to be after making $15 million (including his signing bonus) to lay a season-long egg. But the Braves believe he can be fixed … and if they’re right, Upton won’t be on this list again next year.

4. 1B Mark Teixeira, New York Yankees: three years, $67.5 million (DHM)

Teixeira played in just 15 games during the fifth season of his eight-year, $180 million deal, as a major wrist injury knocked him out of commission. On the eve of spring training, the word is the injury could continue to plague him until June, and possibly all year. So, yes, at this point, we can officially declare this megadeal a bust.

The only remaining source of suspense lies with New York’s infield as a whole. The Yankees obliterated the $189 million luxury tax threshold by signing Masahiro Tanaka, and they sacrificed the first-round draft pick and the compensation picks they would’ve received for losing Robinson Cano and Curtis Granderson, so there’s no reason for them to avoid signing Stephen Drew. Instead, their starting infield figures to be a severely hampered Teixeira at first, Brian Roberts (who hasn’t played more than 77 games in a season since 2009) at second, a soon-to-be 40-year-old Derek Jeter at short, and Kelly Johnson or another below-average option at third. The Yankees don’t care about spending limits, so it’s not fair to say they’re being hampered by Teixeira’s huge deal. But it is fair to say that they’re stuck paying huge sums to a low-impact first baseman who’s now hurting the bank account and the roster. The Yankees spent big this winter, but it’s hard to see them winning anything as long as they’re fielding what, barring catcher, might end up being the worst infield in baseball, and Teixeira is a big part of that.

3. 1B Ryan Howard, Philadelphia Phillies: three years, $85 million (3)

2. 1B Albert Pujols, Los Angeles Angels: eight years, $212 million (15)

The Society of Baseball Nerds has dragged poor Ryan Howard’s name through the muck too many times already, so I won’t belabor the point here, except to say he’s not the one who offered himself this contract, and he’s not the one who put the Phillies in the mess they’re in.

As for Pujols, here’s what I said about him when I ranked his contract as baseball’s 15th-worst a year ago:

Let’s check off the many reasons why any team would want Pujols first. Few players in the game’s history started their careers with a decade as dominant as his was. After a brutal start to the 2012 season, he hit .312/.374/.589 from May 15 on, returning to near-peak form. He’s going to win a bunch of games for his team over the next few years and topple a bunch of milestones too.

Now the bad news. He’s owed a stupefying $228 million over the next nine years, plus $10 million in potential milestone bonuses and more. That’s not an unreasonable payout for a superstar in today’s game, given the leaguewide explosion in revenues. Except Albert Pujols’s days as a superstar may well be gone for good. In 2012, Pujols set career lows in walks, homers, and isolated power (slugging percentage minus batting average), while also posting his highest strikeout rate since his rookie season. He’s no longer an asset on the basepaths, isn’t the all-world defender he once was (though he’s still better than average), and turned 33 last month. He was a four-win player in 2012, and even in this pumped-up market, you don’t pay someone $25 million a year until a player’s early forties when you’re starting at that level. Sure, the Dodgers could always trade for Pujols and make him their new shortstop/no. 3 starter/clubhouse attendant. More likely, he’ll be the Angels’ burden to bear, a still-very-good but basically unmovable player who’ll put a strain on one of the hardest-to-strain team revenue streams in baseball.

Nearly everything I wrote in that second paragraph still holds … except maybe for the part about Pujols still being a very good player, which casts most of what I said in that first paragraph into doubt. Pujols posted career-worst numbers across the board last season, hitting just .258/.330/.437 while missing 63 games.

It’s hard to feel good about Pujols’s chances at redemption when we’ve seen so many monster deals for barrel-chested players on the bad side of the defensive spectrum go wrong. In his prime, Prince Albert had a better glove and nimbler feet than, say, Mo Vaughn. But those secondary skills have vanished, and all that remains is a 34-year-old first baseman who’ll have to move to DH at some point, has eight years left on his contract, and could struggle to hit .290 with 30 homers again, let alone put up the kind of numbers that made him the baddest slugger in the NL once Barry Bonds retired.

While GMs love to pay lip service to the importance of talent up the middle, the siren songs of home runs and RBIs remain tough to resist. But more often than not, paying for them ends terribly. In Pujols’s case, it’s probably not going to take eight more years for team regret to set in.

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

So, let’s see. Even after a season-long 2014 suspension that takes the Yankees off the hook for almost all of his $25 million salary, Rodriguez will still make a tick more than $20 million a year through his 42nd birthday. Amid major hip problems and other maladies, it’s hard to know if he’ll ever be able to play anything close to a full season again, even after resting this year.

The notion of A-Rod playing for the Yankees or anyone else again might be merely hypothetical at this point, anyway. Baseball colluded against Bonds after the home run king hit .276/.480/.565 in 126 games for the Giants in 2007. From a PR standpoint, A-Rod has been 10,000 times the pain in the ass Bonds was, and he’s nowhere near the hitter Bonds was when teams slammed the door in the San Francisco slugger’s face. In all likelihood, the Yankees are going to end up eating the rest of his contract. Given the expectations the fan base has, and given the big revenue hits the Bombers might suffer if they settle for third-place rosters, it would behoove the Yankees to ignore A-Rod’s sunk cost, embrace their Evil Empire reputation, and go buy more players who might one day appear on this list.

This article has been updated to reflect that B.J. Upton’s contract was a free-agent deal, while Dan Uggla’s was an extension.