We all know at this point that long-term contracts for pitchers are very risky; after all (to paraphrase one of your recent posts), pitchers get hurt a lot.  Given that fact, let’s entertain a hypothetical scenario: Let’s say an ace hits the free agent market in his prime, and teams are lining up to woo him.  Conventional wisdom says that, most of the time, the team that ponies up in dollars and years will get the prize, right?  Well, what if a rogue team took a different approach, and instead of offering, say, a six-year, $140m deal, offered a three-year, $90m deal instead?  What do you think would happen?  Would the pitcher scoff at the lower total contract, or would he be interested in the higher annual payout and the lure of another round of free agency in three years?  I’d bet the pitcher would at least think twice about it.  As for the team offering those terms, it would be mitigating the risk of injury to the player; it would save itself money in total dollars committed; and it would have greater flexibility in player personnel decision making in the medium-to-long term.  Food for thought.

– Nate, via e-mail.

Hmm. Hmmmmmmmmmm. That is some tasty food for thought.

It seems like a reasonable enough idea that I’m trying to figure out why it hasn’t happened. I suppose it mostly depends on the pitcher: If he has been so thoroughly injury-free that he and his agent are confident he will be healthy in three years, a deal like that would make  a lot of sense for him. Of course, if that were the case, the team would also probably be reasonably confident that the pitcher would be healthy in three years and might prefer to lock him up for less money per year over a longer term.

I guess the only even vaguely comparable situation is when Roger Clemens signed a couple of massive part-year deals with the Astros and Yankees in 2006 and 2007 (Ed. Note: And he is BAAAACK!), but in those cases I’m pretty sure it was Clemens limiting the length, doing his own version of the Favre festering-boil thing, only in Clemens’ case with an actual festering boil.

Otherwise, maybe it has something to do with the way teams want to structure payouts? As Mets fans have all now seen, teams can invest and earn interest on the money they owe players in the latter years of contracts, so perhaps it behooves the team to avoid giving a player so much money so quickly?

But really, I don’t know. If I had to guess, I would figure it is the agents — smart enough to vote down a confident player who believes he’s invincible — that get in the way of that type of deal. They probably convince the pitchers — rightfully — that they’re in a dangerous trade, and that the security of a $140 million deal (in this example) is better for them and their families. But I’m probably missing something. Some union thing? Any ideas?