Roger Clemens isn't going to pitch again. Even Yahoo Sports has removed him from their active list. So he'll retire with 354 wins.
Maddux just won game 350, so he ought to pass Clemens sometime in July.
As I noted a year ago, Clemens' lead has been shrinking since 1991.
In addition to "Winningest Pitcher of His Generation", he'll probably lose the "Strikeout King of his Generation" title sometime later this summer too, if Randy Johnson stays healthy. I tracked the strikeout difference between them earlier. Clemens got a few more strikeouts since that last post, while Johnson was hurt, and they were about tied last year. So far Johnson is punching out 5.6 guys per start. As of today, Clemens is 28 strikeouts ahead of him:
Randy Johnson's back could give out at any time, but if he can stay healthy, he should pass Clemens around the Fourth of July.