Could Pettitte Win 300?

David Pinto ponders the question: 

The more I think about it, the more I’m convinced Andy Pettitte could easily win 300 games. He’s eighty wins away right now at age 37. He talks about retiring, but his competitive spirit (and large paychecks) keep bringing him back.

He’s a left-hander who induces ground balls. The way balls are flying out of Yankee Stadium to rightfield, the probability exists that Andy’s combination of physical attribute and pitching skill will prove very valuable to the Yankees (although he’s allowed seven of his eight home runs in the Bronx this season).

Finally, Pettitte has the potential to remake himself into a slower pitcher, to become Jamie Moyer. Moyer didn’t start winning game in earnest until he was 33. He totaled 59 wins at that point and now has 250. Andy might get some coaching from Mike Mussina in this regard. That will allow Andy to be effective as age takes it’s toll.

I don't think the fact that Pettitte seems to toy around with retirement just about as much as anyone this side of Brett Favre can be glossed over. He's a family man and it's often said that being away from them for so long takes a toll on him. I get the feeling that Pettitte is thisclose to hanging up the cleats at the end of every season, but Pinto is right... he does keep coming back. 

Logistically, let's see how this would work: Pettitte is on pace for 15 wins this year which is reasonable considering he had 14 and 15 in his past two, respectively. That would leave him at 230 and 38 years old after this year. Even if he continued to win 15 games a year, it would still take him nearly 5 years to get to 300. Does anyone think Pettitte is going to keep trucking 'til he's 43? He has admitted to being injured for the second half of last year and his back acting up as we speak.  

Lastly, Jamie Moyer is the exception to the rule, a total outlier who shouldn't be used as a comparable to anyone. How many pitchers in the majors are older than 43 right now? Two: The Big Unit (45), Moyer (46). Kenny Rogers (another lefty) turned 43 last year and seems like a better comparable for Pettitte than either of the other two (B-R doesn't think any of the three are in Pettitte's top 10). The Gambler won 61 games from 2004-2008 (ages 38-43) playing in Texas and Detroit but his effectiveness steadily eroded towards the end.  

I suppose anything is possible, and it's fun to imagine someone on the Yankees becoming a 300 game winner (I'm not counting Clemens since he only won a relatively small portion in pinstripes - 83). But if I had to bet, I'd put my money on Joba Chamberlain before Andy Pettitte.