There's a fair bit of debate about the demise of the 300-win pitcher these days. With the 5-man rotation, teams keeping star youngsters down on the farm to hold back their arbitration clocks, and the constant risk of injury, it's hard to project any young pitcher today to reach the 300-win plateau.
Let's take a look at Roy Oswalt. Roy is 32, with a career record of 137-70 and career 3.23 ERA. Oswalt has two 20-win seasons to his name, and has 30-plus starts for six straight years. He obviously has a ways to go before he's in the discussion for 300; let's be optimistic and assume Roy can average 15 wins a season for the next 6 years. That would bring him to just 227 wins at age 38. The simple truth is that even top pitchers like Oswalt need to pitch past age 40 to have a decent chance of 300 wins. As a smaller guy, Oswalt doesn't have the size we tend to associate with the 40-year-old pitcher. There's a worry that his velocity won't keep up at such an advanced age.
Nevertheless, Oswalt has a good shot to be in the Hall. He's yet to win a Cy, but has been in the top 5 vote-getters five times. His .662 w/l % is third-best among active pitchers, ahead of Roy Halladay, C.C. Sabathia, Randy Johnson, Tom Glavine, John Smoltz and many other potential inductees. Even if Roy goes 90-80 for the rest of his career, he'll still finish ahead of Glavine and Smoltz.
The 20-win seasons are another point in his favor. As they become increasingly rare, they're of course more notable which means more opportunities for writers to point out to everyone just how special Roy is. With one or two more superlative seasons, Oswalt can complete the sort of resume necessary to convince Hall voters. At this point, a Cy Young would probably cement his case, though that's tough when you pitch in the same league as Lincecum and Santana.
Oswalt is coming off his worst year in the majors. Back problems cost him starts as the summer progressed and the Astros shut him down in mid-September. Under contract for at least two more years, the Astros may handle him carefully in 2010. The Astros, also, aren't likely to be a competitive team in 2010. They've got several holes to fill in their lineup and their bullpen is lacking, so Oswalt may have a hard time getting 20 wins no matter how well he pitches. The 2009 season did serious damage to Oswalt's Hall chances, between only getting 8 wins, the back injury, and the continued stagnation of the Astros. Furthermore, Oswalt's outings have been getting consistently shorter- he fell from 6.5 innings/start in 2008 to 6.0 in 2009. It's much harder for a six-inning pitcher to rack up wins. It's easy to imagine Roy only averaging 12 wins a year from now on even if he can maintain a 3.30 ERA.
2010 will be a key year for Oswalt. If he can bounce back to the 200-inning level, I like his chances to continue piling up wins. He'll be an interesting one to watch. We'll revisit his HOF case next year.