[Jeritron]

Originally Posted by Supreme Olajuwon I don't see Oswalt pitching into his 40s. Halladay and Santana didn't become full time starters until they were 25 so Buerhle has a 3 year head start on them. Sabathia's body will eventually quit on him. Zito could conceivably pitch until he's 50 so I guess he's got a decent shot, but I seriously doubt he'll come close.

I don't know, I'd put Halladay above Buerhle if I were a betting man. It depends where he ends up in the near future, and how long he holds up. He can stand to win a lot more games in the next 8 or so years.

Either way, I wouldn't peg either one of them to win 300 games, or anyone active for a very long time. Nobody in mid-career is on pace to do so, and with the young guys it's too early to tell.
There's also the possibility that Randy Johnson may be the last 300 game winner for a long long time, or possibly ever.

The nature of the game changes, and so does pitching. Certain milestones become increasingly more common, or are phased out to become unatainable.
I've heard legitimate arguments that the age of the 300 game winner is gone.

Randy Johnson would have reached 300 much sooner if he wasn't on shitty teams that constantly failed to give him run support. That's why I think that's such a factor here. If Halladay lands on a respectable ballclub that wins 100 games perenially, he can pick up a few more wins here and there.
Run support hasn't been a huge issue for him in Toronto, but I'm sure it's cost him some tough no decisions here and there.

I'm of the mind that the next 300 game winner is probably just starting their career, or hasn't even been born yet.