So, last year this book was published:
Author Dan Schlossberg, who has written many fine books about baseball, ultimately answered the subtitled question thusly: "The only certainty is that no one is going to join the club in the next few years."
Which is manifestly true. Unless you count Jamie Moyer (which you probably shouldn't), there's not a single active pitcher today with even 200 wins. Tim Wakefield leads the way with 198, and he'll soon turn 45.
After Wakefield, the next two on the list are 34-year-old Roy Halladay (180) and 35-year-old Tim Hudson (35). While I wouldn't want to assume anything about Halladay, to reach 300 wins he'll have to average almost 20 wins per season through his Age 40 season. Or pitch until he's 42, and average 15 wins per season. Etc.
It's definitely possible, but obviously unlikely. Entering this season, Bill James' method gave Halladay a 42-percent chance of winning 300 games. Based on what Halladay's done this season -- 11 wins so far -- he's basically held steady at around 40 percent.
According to James, Sabathia entered this season with a 38-percent chance of winning 300 games, but a) that seemed low to me, because of Sabathia's relative youth, and b) the percentage can only have gone up this season.
He's won 14 this season already, and is a great bet for 20 or more.
You can do the math however you like, but Sabathia's going to finish this season with nearly 180 wins, and perhaps 10 more seasons in which to add another 120. Considering that he's been averaging 20 wins per season for the Yankees and figures to pitch for the Yankees for another few years, at least, the math is going to start looking awfully friendly to him.
There are three potential roadblocks ...
1. His team - Again, as long as he's pitching for a good team, he'll win games. While there's no guarantee that he'll be a Yankee for Life, he's not likely to spend any real time with the Royals or the Astros in the foreseeable future.
2. His arm, etc. - Anybody can get hurt. Not so long ago, Johan Santana looked like one of the better candidates for 300 wins. Now he's not even worth thinking about. And there certainly is a lot of mileage on Sabathia's arm, given his workload in both the regular season and in October.
3. His conditioning, etc. - I spent at least a few years being skeptical about Sabathia's future because of his unique physique. But you know, it seems to work for him. While Sabathia might never again pitch as well as he pitched in 2007, he's still fantastic and doesn't show any signs of decline. We just don't have enough examples of top starting pitchers built like this, where we can draw any meaningful historical parallels. Mickey Lolich? Yeah, he was basically finished in his middle 30s. But he's just one (exceptionally large) man. We need more (exceptionally large) men before we can draw any conclusions about pitchers of Sabathia's "type".
Have we seen the last of baseball's 300-game winners? I am absolutely convinced that we have not. I am moderately convinced that Sabathia or Halladay will get there. And it shouldn't be a shock if both do.