After being stuck on 295 wins for a month and a half, Tom Glavine has won two straight starts, and it’s a foregone conclusion that he will become baseball’s 23rd 300-game winner in short order. Sadly, once he does we may never see the feat again. After Roger Clemens, Greg Maddux and now Glavine and Randy Johnson have made their march to the cusp of 300, there are no more veterans on a collision course with the milestone.

With 284 wins, it is not even guaranteed that Johnson will reach the mark. The Big Unit is only 16 victories shy and has pitched well in 2007, but his balky back has flared up on multiple occasions this year. Considering Johnson’s determined (and abrasive) reputation he may stick around long enough to reach the mark even if it takes two or three more injury-riddled seasons. He’s a first-ballot Hall-of-Famer, and it would be a surprise if he called it quits before win number 300, but don’t put him on the list in Sharpie just yet.

After Glavine—and perhaps Johnson—reach the mark, there are no other veterans for whom the plateau is imminent.

Mike Mussina? Nope. Moose has always been a great competitor and has the fourth most wins among active pitchers (behind Clemens, Maddux, Glavine and Johnson), but his recent struggles, age (38), and long road to go (243 wins to date), rule him out.

David Wells? He can give you a good game when he’s tired, hurt, or even hungover, so his advancing age (he’s 44) doesn’t rule him out. Still, even if Wells were to pitch until he’s 50, he would be hard pressed to come up with the 67 wins he needs to join the elite club. Sorry Boomer.

Next up among active pitchers is Jamie Moyer with 223 wins and Curt Schilling at 213. Neither is young enough to make a serious run at the mark and Schilling is having injury problems.

Pedro Martinez, one of the most dominant pitchers of the last decade, is a far cry from the mark with only 206 wins. He should still make the Hall, but he won’t sniff 300.

Yankee lefty Andy Pettitte is an interesting case, since he has 190 wins at 35. If he follows in the footsteps of his buddy Clemens and pitches into his 40s, Pettitte could reach 300 by averaging about 13 wins over the next 8 seasons. Still, that’s a little much to ask from a guy who has already hinted at retirement, so don’t count on it.

With the pitchers closest to the milestone unlikely to reach it, the natural inclination is to turn toward younger stars that are on pace to join the 300 Club. Unfortunately, it’s difficult to imagine any of today’s top pitchers reaching the mark.
 
Just as the dilution of pitching talent, performance-enhancing drugs, and smaller stadiums have led to the cheapening of the 500 home run plateau, the 5-man rotation, the rise of middle relief, and the emphasis on pitch counts have made the 300-game winner a dying breed.

If 30-year-old Houston ace Roy Oswalt wins 18 games this year, he’ll have to average 18.4 wins/year for the next decade in order to reach 300 at 40 years old. Toronto’s Roy Halladay, also 30, is in the same boat as Oswalt. Johan Santana is only 28, but with 86 career wins to date, he will need to win at least 17 games a year until 2019.

Looking at these aces, and considering the fact that all have the deck stacked against them to win 300, it begs the question if we will ever see a 300-game winner again.

While I don’t foresee it happening, I’m not ready to rule it out completely. It will be tremendously difficult, and in order for a pitcher today to win 300 games he will need to draw the best characteristics from each of today’s young aces.

First, it’s imperative the pitcher goes deep into every game he pitches, thereby avoiding turning the ball over to middle relievers, the chief weakness of most teams. By handing the ball directly to the closer or primary setup man, a pitcher immediately improves his chances of winning the game. So the next 300-game winner will need to be a workhorse (think C.C. Sabathia).

Secondly, dominance is supremely important. A pitcher does not need to be overpowering like Clemens (just look at Maddux and Glavine), but certainly does need to put up 15-20 wins year in and year out. (think Johan Santana).

Third, you have to stay healthy. When looking at the most recent entrants into the 300-win club, not one had a significant injury at any point in his career. So you can pretty much rule out Francisco Liriano, Ben Sheets, Josh Beckett and all the other young guns that have had a hard time staying on the mound.

Finally, it certainly doesn’t hurt to get some run support. Pitching 7, 8, 9 innings and giving up two runs is great, but if you’re team only scores one, it doesn’t go in the win column. Clemens always pitched for decent offensive teams up through his 300th win, and he might have 370 wins instead of 349 if Houston had been able to score for him the past few years. Similarly, Maddux and Glavine pitched for outstanding Braves teams for years and their old teammate John Smoltz might be a 300-game winner too if he hadn’t paused to become a dominant closer for a few seasons. Being able to win on a day when you don’t have your best stuff is hugely important for great pitchers. Regular offensive help is an absolute necessity for the next 300-game winner.

With all things considered, the two pitchers I expect to have the best chance of being the next 300-game winner are Cleveland’s C.C. Sabathia and San Diego’s Jake Peavy.

Sabathia will be 27 this July, and already has 93 wins (for those of you keeping score at home that puts him ahead of 2-time Cy Young Winner Santana, who is also a year older). Sabathia goes deep into games (he has averaged 6.1 innings per start over his career and is averaging 7 this year); he pitches for a team with a young core that should be in contention for a long time; if he leaves as a free agent winning teams with large payrolls will be among his suitors; and he’ll reach the mark by 40 averaging 16 wins a year. For a pitcher just entering his prime and on pace for a monster year (12-2 at press time), 16 wins a year sounds within reach. Another thing to consider: Sabathia has only failed to start at least 30 games in one of his six seasons coming into this year.

Even though Sabathia is the most likely to be the first 300-game winner of pitchers currently under 35, it’s important to remember that he has only won 15 or more games in two of his first six seasons. He will almost assuredly beat that number in 2007, but time lost to injury or a poor season can seriously derail his shot at 300.

Peavy, having a monster year for the Padres, is a long way from the number, as he has only 66 career wins to date. Still, you never want to close the door on a 26-year-old that averages 6.1 innings per start and seems to have finally figured out how to enforce his will on opposing batters by dominating with his stuff. Peavy could win 18 games per year for the next decade, which would put him at 237 wins at age 36. Not a guarantee, but certainly in position to challenge the premise that the 300-win barrier will never be broken again.