It's seems very unlikely anyone will come close again. Too many factors work against it, just like it's unlikely there will be another 30-game winner. It requires you win 15 games a year for 20 years, and with the shorter starts and five-man rotations, that's pretty hard to do. The DH used to be a positive factor (since you didn't have to pinch hit for your starter in a close game), but that's become less important. With pitchers coming out of the ballgame after 100 pitches, they are slightly less likely to be the pitcher of record when they leave. If that happens once or twice a season, it can make a big difference over the course of a career. In addition, young pitchers tend to be brought along more slowly. Look at Johan Santana. He'a 28 and needs 211 wins. If he pitches until he's 40, that's over 17 wins a year. In the last five years, he's won less than 17 twice (I assume he'll reach 17 this year). In 2005, he had a very good season statistically, but only won 16. And if he's injured at all and misses part of a season, he's going to find it hard to make the 17. Obviously, it's not impossible, but it's highly unlikely any pitcher will be able to get the innings needed to get to 300.