So according to this article, Tim Lincecum of the Giants prefers to take his contract status on a year to year basis rather than signing a deal to buy out his arbitration years. All signs point to him having 4 arbitration eligible years with the first one being the 2010 season. If he signed long term now, he could get definite money for five years with a team option or two probably attached.
Now let's assume that there was no chance of him being signed long-term for the '09 season as he isn't yet arbitration eligible. Lincecum is 24 this season which means that the first possible year of his free agency would happen when he turns 30. He's currently 12-3 with a 2.63 ERA in over 157 innings pitched. He's got 9.99 k's/9 and 3.31 walks/9 while only allowing 9 home runs. Yeah - this guy is good.
There is no doubt that he has the potential to make A LOT more money through arbitration and he will be 30 by the time he hits free agency (possibly 32 or so if he signs a contract with a couple of options.) My problem with this is that you never know how well a pitcher is going to hold up over the course of several years and it is foolish to not take the sure money now than risk not making any in the future (even it means making slightly less over the long haul.)
A couple of contract examples that worked out well for pitchers? Barry Zito, Dontrelle Willis, and dare I say Carl Pavano (man what a waste he was.) Guys like Matt Cain, James Shields, David Price, and even Scott Kazmir (yes, I mention 3 Rays because they were smart enough to get these guys for a good price) may seem like a good deal for the clubs now, but you never know when a player will lose the edge or go down with a major injury.
Long story short, my opinion is take the money while you can. That contract you sign for your arbitration years can set you up for life if you're smart - who knows how long you'll actually last in baseball.

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