Let me spare you the suspense. There are only 2 legitimate candidates within the next 15 years: CC Sabathia and Roy Halladay. Sabathia has more margin for error because he is younger. The key question for Halladay, injury aside, is whether he’s more Mike Mussina or Randy Johnson. Randy Johnson is 45 years old and had 70 wins to go from reaching 400 when he turned 40. Mussina retired after turning 40 and only had 40 wins to go.
Most pitchers don’t throw much past 40, and the ones that do are usually soft pitchers, like Jamie Moyer. Halladay is a big, hulking power pitcher and workhorse. He logs many innings, leading the league last year. If he’s like Nolan Ryan or Randy Johnson and he can keep throwing to 45, I think he’ll hit 300. If he’s like other mortals, then no. Right now, Halladay has 140 wins and is going on. He is the best pitcher in the game right now.
CC Sabathia is 122 years old, but he’s only 28 and now he’s wearing a Yankees uniform. He’s another really big and beefy great power pitcher. It’s possible he can rack up enough wins by the time he’s 35 to try.
A lot of people say that no one will ever get to 300 again. They said that after Clemens and Maddux and Glavine and now Johnson. They all did it in an era of specializing in relay and 5-man rotations and even steroids! It can be done, especially now that home runs have dropped dramatically with steroid testing. It takes a monster of nature that is both very good and very lucky. Most pitchers get hurt and can’t last until they’re in their 40s. I guess Halladay is the type who would do it if he was in sight, like Johnson did. There were rumors that Andy Pettitte might retire soon, and he’s the closest one that isn’t Jamie Moyer. He’s at 220 and not even 37 yet, but it doesn’t seem like a possibility for him.
I don’t think anyone will get to 300 wins in the next decade unless Tim Hudson really fires up and is 146 wins and 34 years old. There’s a decent chance the current generation of great pitchers will: Sabathia, Santana, Halladay, Oswalt. It won’t happen for a while, so enjoy the Great Unity achievement.