Ever since baseball teams and players agreed to multi-year, guaranteed contracts (which, basically, has been, ever since baseball became professional, look it up) there have been contracts that are millstones weighing a team down. After a year or two, you go, “Why did they sign that bum to that deal?”

For me, the move that made me shake my head the most was Texas signing Mark Clark in 1999. Clark was coming off of a 9-14, 4.84 season for the Cubs in 1998. His peripherals were better, sure. But aside for a great stretch after being traded to the Cubs in 1997, he was nothing more than an average big league starter. His best WAR was in 1994, a 2.4 season derailed by the strike.

Texas signed him for $9 million, which was a big deal then. Clark gave up 110 earned runs in 118 innings, and retired to his ranch. By all accounts, he was a great guy, but man, that was a bad signing by Texas, and indicative of their inability to corral pitching during that era. Clark no doubt treats his agent to steak and champagne occasionally.

Now, with revenue increasing, signing players to big money deals aren’t unusual. Teams take out insurance to offset these deals in order to safeguard them from injury. Still, long-term deals for big money can really hamper a team. Even teams like Boston and the Dodgers have SOME budget to deal with, and having a worthless contract on the books for five years can hurt a team. They can’t collect on insurance if a player just stinks.

So here’s a look of players that are going to be earning big money after 2016 with contracts signed in 2015 or before, and now they seem a bit, shall we say, questionable as to if there’s a payoff in the future. Each division will be highlighted, so you all have time to laugh and point.

Pablo Sandoval – Boston (2015 – 5/$95 plus a team option in 2020) – The Kung-Fu Panda had one outstanding season, in 2011, and good seasons in 2012-2014. He was also a player who had a propensity for weight problems, and his defense was going to slip. Still, Boston threw money at him, and has been rewarded with 512 plate appearances of -1.1 WAR, and a torn labrum.

Russell Martin – Toronto (2015 – 5/$82) – Martin still has skills, but he’s most valuable when he’s putting up league average offense and playing catcher. Will be be catching in 2019? And do you want to pay $20 million for a first baseman or DH who hits juts a little better than Justin Smoak? Didn’t think so.

Troy Tulowitzki -Toronto (2015 – 6/$118 plus a team option in 2021) – Death, taxes, and agate type announcing that Troy Tulowitzki is on the 15-day DL. If healthy, he’s probably still a four to five win player. He last played more than 140 games in 2011 and has missed 30 games this year. So you tell me if he’s going to be a four to five win player in 2019 and 2020.

Melvin Upton – Toronto (2013 – 5/$72.5) – In fairness, Toronto didn’t sign Tulowitzki or Upton. Also, San Diego owns about $11 million of his contract next season, and they didn’t sign him to this one either (thanks, Atlanta). Since this contract was signed, his TOTAL WAR is 1.1. His K/W ration this year is 137/28. Will he even be on a team for the final year of his contract?

Wade Miley – Baltimore (2015 – 3/$19.25 plus a team option in 2018) – This one wasn’t as long term, but it’s still puzzling why Boston committed this much money to Miley, who has been average at best since his 2012 debut. The kicker? They didn’t need to sign him for this much – he was still under team control (arbitration eligible, but still). Boston flipped him to Seattle, and the M’s bailed on him as well. Smitty’s probably going to grit his teeth through all of Miley’s 2017 starts.

Ubaldo Jimenez – Baltimore (2014 – 4/$50) – Jiminez was the real deal back in Colorado, which seems oh so long ago. Cleveland traded four players for him (but the only one worth a hoot was Drew Pomeranz), and they got almost jack squat for their trouble. Still, the Orioles inked him and he pitched like a #3 starter in 2015. Unfortunately, he pitched in 2014 and 2016, too. He’s another one that could be out of the league before his contract is up.

Adam Jones – Baltimore (2013 – 6/$85.5) – I was surprised to put Jones here and not Chris Davis (though that may be written about in 2018 or so). Jones has two more years on this deal, and while he was a great player the first two years of the deal and a good player last year, he’s been average this year. His defense has regressed, and he’s 30 years old. If he’s not hitting home runs, he’s not going to be worth it.

JJ Hardy – Baltimore (2015 – 3/$40 plus a vesting option in 2018) – I’m not picking purposely picking on the Orioles, and yes, when this contract was inked Hardy had won three straight Gold Gloves. This isn’t the Mark Belanger era, though, and Hardy’s sub-par offense and injury issues are going to really limit his true value for 2017. The problem is that Baltimore has no other option.

Jacoby Ellsbury – New York (2014 -7/$153 plus a team option in 2021) – “The Yankees are just going to buy their way to a pennant each year!” said the mediots and yakkers. No, they’re not, and here’s one reason why. Ellsbury can still play defense, yes, but he’s had past injury bugs and is now teetering on being an offensive liability. An OPS+ of 85 at age 32 isn’t great – and they’ve got four more years of this, too.

Brian McCann – New York (2014 – 5/$85 plus a team option in 2019) – I’d think twice about signing catchers over the age of 30 to any sort of long term contract. Somehow McCann got MVP votes in 2015 for a 2.8 WAR season. This year in 100 games he’s at 0.9 WAR, his defense is slipping, and he’s 32. He made his name early in his career for the Braves, but he’s well past that now.

Chase Headley – New York (2015 – 4/$52) – Did you know Chase Headley was due to make $13 million a year until 2018? I didn’t. He’s been consistent, and if you want a third baseman to slash .255/.327/.370 every year go for it! He’s also 32, and father time may not be kind.

Brett Gardner – New York (2015 – 4/$52 plus a team option in 2019) – These aren’t the Yankees you love to hate. I mean, I like Ellsbury and Gardner and Headley’s done nothing wrong. (McCann, though, can go soak.) It’s just that the Yankees are like the owners you love to draft against in a fantasy league. They’re spending all their money on players that they personally like, and have ‘names’, regardless of their true value. Gardner had a pretty good 2015, but his offense is slipping (OPS+ of 93 this year), he’s never been a great defender, and his stolen base total is going to continue to shrink. Oh, and he’s 32 as well. The Yankees haven’t seem to gotten the memo that offensive players peak at age 27 or so.

Evan Longoria – Tampa Bay (2008 – 15/$144.5 plus a team option in 2023) – Tampa has only three players with non-arbitration contracts signed for 2017 – Logan Forsythe, Chris Archer, and Longoria. Archer’s not had a great year, but he’s not stunk, either, and pitching for the Rays this year is an adventure all into itself. Longoria’s had a great bounceback year in the relative quiet of Rays games (their stadium should be called The Library or something since it’s so quiet). The reason he’s here is that if he has back to back years like 2014 or 2015 are trouble for a team that has such limited resources. You need him to be a five or six win player. The big concern for me is his comparable players. The most similar player to him for his entire career is Phil Nevin. The most comparable player at age 29 was Eric Chavez. His age 28 comp was Aramis Ramirez. After age 30 Ramirez had one good year, one great year, two okay years, and three lousy years. Tampa can’t afford just good or okay from him if they want to compete long term with their current structure. (Note, if Tampa moves and actually becomes as flush with cash as the other 29 teams, then Longoria could be taken off this list…)

I’m as surprised as you are that Boston only has one contract here. It’s too early to tell about David Price or Rick Porcello, though. Check back in 2018.