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There's absolutely no indication that fewer and fewer pitchers will reach 300 wins in the future. Yes, we're very unlikely to see a return to stating pitchers winning 30+ games a season, and indeed are likely to see fewer and fewer 20-game winners, but we're likely to see more and more guys pitching effectively past age 30.
We've got 130 years of major league history, and 22 guys have reached 300 wins. Of those 22, 8--more than a third--have reached that level since 1980, and Glavine might reach it this year (needs 10 wins and had 15 in 2006; I suppose that Randy Johnson could to, but I don't see him winning 20 games at age 43--but if he comes back in 2008 at age 44, he'll likely get there then ). If anything, 300 winners are more common now than any time since the 19th century.
My opinion hasn't changed any since then, though obviously my comments about Glavine and Johnson are a bit outdated.
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I'll bet you $50 that there's at least 2 pitchers active in the majors this year who eventually get to 300 wins, not counting Johnson (who I'm think might be done). (And we'll probably have to wait about 20 years to find out for sure, but that's OK--I don't mind waiting to collect.)
Mussina still has a chance, at least, though I don't think he'll make it. Some of the other guys who currently have 200+ wins I suppose might make it if they last as long as Ryan did, but the best bets are younger pitchers who are not anywhere near that yet. Johan Santana is 28, and is already up to 89 wins, and C.C. Sabathia is 2 years younger and has 6 more wins. Do you really want to argue that it's not possible for either of those guys to make it to 300 wins? And if neither of them do it, maybe Roy Halladay or Dontrell Willis will, or maybe Ben Sheets. Or maybe some kid who's in his first season, and will end the year 2-3 with an ERA of 6.49 (Santana's marks his first season). While the odds will be strongly against any individual pitcher we might look at making it, there are enough pitchers who have a bit of a chance that the cumulative odds are that someone will do it.