The Most Difficult Contract Decision in the History of Baseball

By Grant Brisbee - Editor

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Jan 6, 2012 - The perfect contract extension should make both sides wonder if they gave up too much. The player should wonder if he left money on the table, and the team should wonder if it committed too much for too long. No one should be happy. And a corollary to that should be that contract extensions should never be easy. If an extension is easy, it's likely that one side is getting hosed.

But even in a framework in which every contract extension should be difficult, allow me to present the Most Difficult Contract Decision in the History of Baseball:

Josh Hamilton.

Alright, maybe the whole most-difficult decision thing is a little hyperbolic, but the best way to describe Hamilton is as a swirling miasma of things that make you want -- and not want -- to commit over $100 million to him. We're used to him now, so maybe the story has lost a little ridiculousness. It never should. A reminder:

• Hamilton was a 21-year-old in A-ball. He left baseball for personal reasons.
• He came back as a 25-year-old in low-A and took 50 at-bats.
• He then demolished Major League pitching for the next five years.

Forget about how I skipped over the "personal reasons" as if he had to run something to the post office. How many players in the history of the universe could have followed that path? He left A-ball at 21, took a four-year hiatus, and then started hitting like a superstar the second he returned to the highest level of professional baseball?

It stands to reason that this Hamilton kid has more natural talent in the dried skin he leaves behind when he uses pine tar than most baseball players will ever have. And he's a four-time All-Star and former MVP, so it's not like this is theoretical talent. Hamilton is one of the very best players in baseball right now.

But that's the stuff that goes into the shiny binder that his agent will prepare. That's only the good stuff. What makes him the toughest contract decision in the game is a list of facts that's as ominous as the good stuff is good. He's 30, injury-prone, and those personal reasons glossed over up there aren't problems that will ever fully go away. The new hitting coach for the Milwaukee Brewers, Johnny Narron, was previously his accountability partner, which led the Rangers and Hamilton to find a new person for the job -- Hamilton's father-in-law.

It feels a little craven to reference Hamilton's past and continuing struggles with addiction every single time he comes up, but it would be silly not to take it into account. If addiction is a disease -- not especially interested in getting into that debate on good ol' Baseball Nation, but let's at least acknowledge that it's a position that plenty of people hold -- it's as relevant as a player's history of microfracture surgery.

It all adds up to a player who should get a big-money/short-term contract. And by short term, we're talking three or four years, even if that sort of commitment makes you nervous. Hamilton's a free agent after this season, and it's possible that the Rangers will work something out before the year is up. He's not only popular in Texas, but it's a team at the top with a great blueprint and bright future. And they'll certainly make an effort to keep Hamilton.

But if you're Hamilton and his agent, you're hoping for another great year, which would lead to a team marlining cartoonish sacks of money Hamilton's way. In the open market, there's a good chance that there's a crazy team. And when that wild-eyed team (or owner) looks at Hamilton, they'll see a face of a franchise -- Captain America mixed with Andy Dufresne mixed with Duke Snider. If he has another MVP-caliber season, the bidding will be ferocious.

Adam J. Morris of Lone Star Ball has a great look at the looming decision the Rangers has to make, focusing more on the high-average/low-walk profile of Hamilton, and he concludes that …

Hamilton is better than (Alfonso) Soriano, not as good as (Vlad) Guerrero, but I suspect that his aging pattern will look similar. If he stays healthy (a huge if with him anyway), Hamilton will probably be solid in 2012, 2013, maybe 2014. But around 2014-15, I expect Hamilton to start sliding, and when the slide comes, it will be dramatic and ugly. Between injuries and skill deterioration, I expect Hamilton to be done as a regular by 2016.

So what's the right answer for the Rangers? Pfft, like I know. That's why this is the Most Difficult Contract Decision in the History of Baseball. Good luck with all that, Rangers.

Read More: Josh Hamilton (CF - TEX), Texas Rangers

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