Not the movie.
I'm mildly obsessed with career wins, specifically 300 game winners. Presently Clemens has 348 and Maddux 337, a rare instance where two pitchers in the top ten are active.
Barring injury, Glavine will almost certainly get to 300 this year--he's at 295 right now and is pitching well. The Very Large Unit is at 282. He won't get there this year. Maybe next year, if his back will let him.
Who's next? No one, not for a while. If we look at active 200 game winners, none of them will get to 300. Mussina's 38, and I doubt he has 59 wins left in him, considering the last four seasons he won 57. He appears to be running out of gas.
Boomer, Jamie Moyer (quick, who knew he had more wins than Pedro or Schilling?), Kevin Brown (why is he on the "active" list?), Kenny Rogers, Pedro (love him!), and now Smoltz, who may have had a chance if he didn't spend four years relieving, but now is making a very strong case for the Hall of Fame...none of them are going to get there.
Looking further down the list, the next likely candidate is Tim Hudson, who's a long 176 wins away. It's possible that he could average 15 wins for the next twelve years. I think a better bet is Roy Oswalt. He's won a lot of games already, but he has to get on a team that score some runs for him. The rest of the list--Buerle, Halladay, Sabathia, etc.--is so far away that speculation is pointless, no matter how good Johan Santana is. It's at least ten years away, probably more. So after Glavine and Randy Johnson, there won't be any 300 game winners until, oh, 2018, maybe 2020.