10a. Jonathan Papelbon 33
2012 – 2015, 4 yrs/$50M, 2016 option for 13 million vests with 100 games finished between 14-15 or 55 finished in 15.

Paying big money for closer has become passe, but Ruben Amaro didn’t get the message when he signed Papelbon to a 50 million dollar deal after the 2011 season. In his haste to reel in Boston’s ninth inning man he also cost the Phillies a first round draft pick — if he had just waited a few days MLB would have detached draft pick compensation from all relief pitchers. Now if Papelbon had remained the best closer in baseball none of this would have been a big deal. But his fastball has lost a couple ticks during his two plus years in Philly and his questionable personality hasn’t gotten any less so.

10. Carl Crawford 32
2011-2017, 7 yrs/$142M

When Boston signed Crawford to a long term deal before the 2011 season, the knives came out quickly. You don’t pay a player who depends on his legs big money long term, the critics said. Crawford proved them right, immediately struggling through an injury-plagued season and a half in Boston. Then something miraculous happened. The Los Angeles Dodgers agreed to take on the contract of Crawford, along with the contracts of fellow financial albatrosses Adrian Gonzales and Josh Beckett. The next season the Red Sox won the World Series, and now the Dodgers are paying 20 million a year for essentially a fourth outfielder.

9. Josh Hamilton 32
2013- 2017, 5 yrs/$133M

Everybody loves the story of Josh Hamilton: a drug addict who almost threw it all away made good. He was making really good until the second half of the 2012, when pitchers realized he would swing at anything and stopped throwing him strikes. Nevertheless, the Angels gave him a huge contract after that off season. So far, he’s been pretty bad. While there is always chance Hamilton will tame his free-swinging ways, he’s almost 33 now, and that’s an old 33 because of his years of serious drug abuse. This contract could get really ugly.

8. BJ Upton 29
2013-2017, 5 yrs/$75.25M

The length and dollar value on this contract aren’t awful. However, Upton has been exactly that since signing it, hitting 184 in 2013 for the Braves. Maybe the Braves should have done a little (very simple) research here, because Upton hadn’t batted above .246 since 2009 and his defensive has never rated that highly. Sure he’s fast. But you can’t take advantage of your speed when you are striking out 151 times in 446 plate appearance, as he did in 13. His contract is reasonable enough that Upton doesn’t have to be that good to earn most of his money. We’re not betting on it.

7. Prince Fielder 29
2012 – 2020, 9 yrs/$214M

Fielder is a perfectly good player, and in fact more or less earned his money for Detroit during the first year of his contract in 2012. But there were eight more years to go, and the portly slugger only hit 25 homers in 2013, part of a fairly steady decline from when he hit 50 in 2007. He was traded to the Rangers for Ian Kinsler in the off season, and maybe a move to the wind tunnel in Arlington, Texas will help him rediscover his big time power stroke. The craziest thing about Fielder’s ridiculous contract is that now two teams of essentially singed off on it.

6. Mark Teixeira 33
2009-2016, 8 yrs/$180M

Paying over 22 million dollars a year to Teixeira until he’s 36 never seemed all that prudent. However for at least the first few years of his deal Teixeira was able to provide the Yankees some value through his home runs and smooth defensive at first — even if he had become a 250 hitter with declining on-base skills. But Teixeira hurt his wrist in 2013 and those type of injuries can be devastating for power hitters. New York may only be on the hook for three more years, but there’s a solid chance the 60 plus million they owe the switch hitter is going to be dead money.

5. Ryan Howard 34
2012- 2016, 5 yrs/$125M 23 million dollar option for 2017 with ten million dollar buyout

Once the gold standard of terrible contracts, Howard’s deal gets comparatively less terrible every year. That has nothing to do with Howard’s play on the field — he’s been an injured mess the past couple of seasons — but because Major League teams refuse to learn from Ruben Amaro’s mistake and keep giving long-term big money to one-dimensional first baseman in their thirties. As you can see above, bad contracts can still be trade-able and if Howard manages to put up decent numbers in 2014 it’s not out of the realm of possibility the Phillies can eat some salary and ship Howard to the American League where he belongs.

4. Alex Rodriguez 38
2008-2017, 10 yrs/$252.87M

Alex Rodriguez’s contract got a little bit less horrible when he suspended for the 2014 season, meaning the Yankees don’t have to pay him. But even in the Bronx, where money grows from the concrete, the logic behind paying a player with a dodgy PED history 20 million dollars a year until he’s 42 was never very sound. Then there is the 30 million dollars in incentives he will get for home run milestones between 660 and 763. (He’s at 654). We’re pretty confident the Yankees and most of their fans are hoping A-Rod gets hit with another PED positive and is suspended for life.

3. Albert Pujols 34
2012-2021, 10 yrs/$240M

No doubt Pujols was the best player in baseball over the 11 years before the Angles signed him. However the three-time MVP winner had a down year in 2011 and was already showing his first signs of decline  when Arte Moreno gave an average of 24 million a year until the age of 41. (Or is it 43, as rumors of Pujols being older than his listed age have long been rampant.) Pujols has been in a straight line decline since joining the Angels and between him and Hamilton … well, at least the Halos have Mike Trout and his terrific new contract.

2. Robinson Cano, 31
2014-2023, 10 yrs/$240M
Maybe it’s a good idea if teams just stayed away from 10 yrs/$240m contracts. This head-scratching deal may have been good for Jay-Z, but he can’t imagine it being a winner for Seattle, who will be paying a mint for a really-good-but-not-quite-great player until he’s 40. We also doubt it will turn out well for Cano; his offensive numbers will slip thanks to his new home’s tougher dimension and he’ll also suffer the indignity of being near the top of every worst contract list for the next decade. Sure he’ll be well paid, but he probably could have been almost as well paid if he stayed in his New York comfort zone.

1. Miguel Cabrera 30
2014-2023, 10 years/$300 million

MLB teams never learn. Or maybe they just don’t care. After seeing big-boned first baseman types Ryan Howard, Mark Teixiera and Albert Pujols all decline precipitously in their thirties, the Tigers still decided to give 30 year old Miguel Cabrera — not a skinny man and one who may struggle with alcohol problems — a 10 year deal. The worst part is they didn’t have to: Cabrera was already signed through 2015. Anyway, Cabrera is pretty great, at least for now, and it’s not your money.

Honorable mention bad contacts: Joe Mauer, John Danks, Adrian Gonzalez, Dan Uggla, Jose Reyes.