It's interesting to see if Verlander can get to 300 wins. He sits at 242 and is pitching as well as he ever has. He will be 40 at the beginning of next season. I know one of his goals is to get to 300 wins, but 58 wins at his age will be difficult. It would seem he would need to pitch another 4 seasons at the bare minimum to reach 300.
If he does make it, I am 99.9% sure he will be the last pitcher to ever get to that mark. Greinke has 223 and is washed up. Scherzer has 199 but is 38 and often injured. Kershaw has 192 and is still an effective pitcher, but he has battled countless injuries the last few years. He's only 34 and is exactly 50 wins behind Verlander. He would need to average 13.5 wins if he pitched until he was 42.
After Kershaw, Gerrit Cole has 127 wins but will be 32 in a few weeks. Even if he averaged 20 wins per season until he was 40, he still wouldn't get to 300.
With the way pitchers are being used and the injuries that seem to be happening to everyone, Verlander and Kershaw would seem to be the last 2 guys to have a shot at 300.