Operation Shutdown

What’s the worst contract in baseball history?

There are a couple ways to look at this. First, and most obvious, are the contracts that provided the least amount of value-per-dollar. Of course, this would require stats, and I don’t know anything about stats, so.

Second is to look at the contracts that were expected to work out, but didn’t for whatever reason. The argument here is that teams were counting on these players to be centerpieces, so when they busted, it was a more devastating blow than your usual bad contract. Eric Chavez is the big one here… arguably Todd Helton and A-Rod II, although neither of those have been out-and-out bad; just not worth their money. Johan Santana. Vernon Wells.

Of course, criticizing such contracts requires hindsight, and maybe you feel contracts can only truly be judged based on the circumstances of the signing. That’s when you go to number three, the contracts that everyone knew were disasters from the moment they were signed… and lo and behold. Carlos Lee, Alfonso Soriano, Barry Zito, Chan Ho Park, Darren Dreifort.

Orioles president Andy MacPhail recently weighed in on the subject and came up with an entirely different criteria. He declared that the worst contract ever signed was Alex Rodriguez’s… first one. The record-setting contract he signed with Texas following the 2000 season, not the ludicrous panicky overpay the Yankees signed him to after his 2007 MVP campaign. I doubt he’d get much argument if he’d picked the latter, but… A-Rod’s first contract contains some of the greatest sustained play in the history of the sport. Why would MacPhail go with that one?

Because, despite A-Rod playing as well as anyone possibly could, the team didn’t go anywhere. They were just as bad in the three years A-Rod was there as they were in the years before he arrived, and got better after he left. They spent all that money and, despite getting everything from A-Rod that they could have ever hoped for, still couldn’t win ballgames, and their attendance and revenue remained static. So they ate a bunch of his contract to have him play for the Yankees.

Normally I would give such a position all the derision it deserves. After all, A-Rod’s contract, record-breaking though it may have been, hardly stopped the Rangers from surrounding him with talent. (Minus A-Rod, their payroll was still in the top half of payrolls, and if you subtracted the highest-paid player from every other team, they move into the top ten.) The Rangers sucked during the A-Rod years because, but for A-Rod himself, the Rangers’ talent evaluation and resource allocation skills were terrible all around.

But really? MacPhail’s an executive. His job is to look at organizations as a whole. The fact that A-Rod had good years in Texas would be meaningless to him, if the team itself wasn’t successful. Even though I think he isn’t valuing  a truly great player enough, I can see where he’s coming from — most “worst contract ever” talk comes from fans, but an executive would have a different take. It’s possible to pay a guy a ton of money and have him earn it… but still make a bad move in terms of what your team needs to be doing. That’s his real point, not any specific trashing of A-Rod.

On the other hand, even from that perspective, there are worse contracts — maybe not as record-breaking, but worse in terms of wasted money and damage to the franchise’s credibility. How about the Mets signing Oliver Perez for $33 million, then refusing to cut him when he stank? Or the Pirates pissing away $4.5 million on Derek Bell, only to have him commence the infamous “Operation Shutdown” and quit on the team when he found out he’d have to compete for a job?

In fact, from the perspective of a owner/executive, I think you could make the argument that the worse contract ever was given to Andy Messersmith. Before that, the players had no real idea that salaries could be as lucrative as they ended up being. Afterwards, they knew they no longer had to work for whatever peanuts the owners deigned to give them. Messersmith opened the door for them, and killed cheap, disposable labor for the owners forever. That’s the contract that keeps on giving.


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