Have you ever thought about how weird it is that your hobby involves debates over the relative salaries of grown men? We might as well sit around and debate the pay schedules of government workers. Check out what they make in Decatur, everybody! Isn't that appropriate/wildly out of line? Let's have an Internet fight about it!
But it's not really about the salaries. It's about the ability of an organization to put together the best team possible, and the salaries directly affect an organization's ability to do that. Maybe it's less weird if you think about salaries like attribute points in a computer RPG, where if you put too much toward "charisma", you won't have any left for … what's that? That isn't less weird? Okay. You get the point. Moving on.
With that written, here are the five players teams shouldn't want to extend before they have to. This isn't a list of players a teams should avoid, but a list of players that teams should let reach free agency before attempting to re-sign them. The risk of waiting is that the player will get more expensive on the open market. But the risk of a proactive extension might be worse.
Seriously, just don't. There is never, never, never a good reason to extend a closer a year before he's a free agent. The worst-case scenario -- the absolute worst -- is that a team has to find another closer. And while I think it's kind of overblown to suggest they grow on trees, cash-strapped teams have been making their own closers from internal options for a couple of decades now. It's possible. And as a worst-case scenario, it's not exactly apocalyptic.
Maybe there's an exception to be made for Mariano Rivera, but that brings up Baseball Truism #49.3:
Mariano Rivera is an exception to everything.
So he doesn't count. If a closer is entering his arbitration years, let him go year-to-year. If a closer is approaching free agency, gamble that he'll still be willing to return after being courted on the open market.
Because if anything happens to that one tool -- or if the other tools get worse and worse -- look out. Every skill will erode at some point. Someday Mike Trout will make that "nnnrrgh" sound that old people make when they reach down to pick up a pen. It will happen to every player. Every tool gets worn down to a nub.
Dan Uggla has one tool: his power. But his home-run total dropped by almost 50 percent in 2012, and he'll be 33 before this season starts. Meanwhile, his non-tools like contact and fielding have been eroding. He was locked up to a five-year, $62 million deal after the best season of his career, and a year before he would have been a free agent. And, wouldn't you know it, that one tool wasn't enough to prevent the non-tools from dragging him down into one-win territory. (At least on Baseball Reference. FanGraphs likes him a lot more.)
If you're still convinced Uggla is worth the contract, I'm going to go on a limb and take the stand that Ryan Howard's contract extension was ill-advised. Seriously. I have data that backs me up, so don't even try it. Now, it's a little unfair to suggest the contract's downfall was entirely due to Howard's one-toolability -- he suffered a pretty nasty injury, after all -- but think about Ryan Howard without his power. Pretty horrific, right? His .423 slugging percentage was a point under Jordany Valdespin's last year.
Wait until the bitter end to make sure that one tool looks like something that can carry the player through a long-term deal.
It's probably not a good idea to extend one-tool players at all, actually.
Mr. Declining Strikeout Rate and/or Rising Walk Rate
Three pitchers, two of whom picked up extensions and one who didn't.
Steady as she goes.
The strikeout decline was a little scary, but the command decline was even scarier. If you're wondering why the Giants made a priority to re-sign Cain but held off on getting too deep with Lincecum, it might have been because there were some internal concerns that Cy Young Lincecum wasn't coming back, and Still Good Lincecum was going to want to be paid like Cy Young Lincecum. The last thing they expected was Bad Carlos Zambrano Lincecum, but that's another story.
The Demi-God (after his best season)
Rule of thumb: If the player that good, he's probably not going to be that good again. Waiting a season will do wonders. When Justin Verlander had his ethereal season in 2011, he wasn't likely to repeat it. Not because his ability was going to vanish, but just because no one is that good all the time. Extending a player after a season like that is paying for an expectation of the planets aligning perfectly and at the right time over and over again. If the Tigers wanted to extend Verlander, they would have an easier time with that now than they would last offseason.
The good current example would be Buster Posey. If he repeats his MVP season, well, he'll still be expensive. But the odds are he'll come in just a little under what he did last year, and an extension would be for a player with the potential to put up MVP numbers. Right now, Posey would ask for an extension that's commensurate with a player who wins the MVP every time he plays a full season. Maybe it's a good idea to wait and see if he really is that player before paying for it.
The Master of Illusion
And now we get to the real inspiration of the post. Is Aaron Hill really good? Or is he awful? No idea. He was worth six wins in 2009, making the All-Star team and finishing 12th in the A.L. MVP voting. Then he was awful, finishing with an OBP below .300 for two straight seasons, including an abominable 58 OPS+ in his last spin with the Blue Jays.
Since joining the Diamondbacks, though, he's been amazing. He's hitting for average and power, and he's taking walks while playing a good second base.
Which Aaron Hill is the real one? No idea. Now, I can see the Diamondbacks signing Hill to a four year, $40 million deal if he were a free agent this past offseason. He hit the snot out of the ball last year, and it's not like the Diamondbacks were overflowing with internal options, so it's not automatically foolish to plug your nose and hope the good version sticks around.
But when the player is a free agent after the coming season … how's about waiting until, oh, June just to make sure? The Diamondbacks had that luxury. And the worst-case scenario was that Hill would hit just as well, and another team would outbid them on a long-term deal for a enigmatic 32-year-old second baseman. Which is one of of the best-case worst-case scenarios I've seen.
All contracts are gambles. Sometimes, though, a team has the opportunity to get a little closer and see if Lenny Dykstra is the casino worker before putting its money down, but they're just a little too eager. Beware these five broad stereotypes. Bewaaaarrre.