So we're in this weird pause for starting pitchers and career wins, with the top active pitcher having only 200 wins (that's Tim Wakefield, who isn't going to add to that very much). I haven't seen it, but I'm sure there are plenty of people saying that the 300 game winner is extinct.
Here's the funny part. 200 wins is, it turns out, the lowest ever for an active leader in wins. Any guesses about what year had the previous record? Turns out it's 1968. Don Drysdale, with 204. It's a serious dry spell; from 1967 through 1977, the leading guy never got past 253. And yet we completely think of that era as a good one for 300 game winners: Carlton, Ryan, Sutton, Niekro, Perry, and Seaver were all pitching then. People have been saying that 300 game winners were going extinct as long as I remember, and yet it still hasn't happened, and I'm confident that it still isn't happening (okay, sorry for being lazy
Roy Halliday is 112 games away, and just finished his 34 year old season. Let's see...he gets 15 a year for four more years and he'll be 52 away through age 38, which would leave him in excellent shape, although of course with pitches...well, at any rate, there's a Favorite Toy calculator over at ESPN, and it gives Halliday a 17% shot. Tim Hudson has a bit more to do and one fewer year...tough, but not impossible. CC Sabathia is in as good shape as you can be at this point, with the Favorite Toy saying 45%. Even someone such as Josh Beckett (125 wins, was 31) isn't as far off the mark as you might thing. Of course, most similar guys don't come close and he probably won't, but would it really shock you if Beckett averaged 18 wins over the next three years? If he does that, he's all of a sudden just a bit behind where Halliday is now.
My guess is that there are three to five active pitchers who will hit 300 wins, and I'll be shocked if there isn't at least one.
...and looking around before I finished this, I came across a John Dewan article from November making basically the same point, except for the Drysdale thing, but with much better calculations on the Favorite Toy. So ignore my calculations above (sorry, too lazy to remove them), and look at his table.