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.