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Come Fan with UsSaturday, June 27, 2026

Roy Oswalt: One of the best of his generation

It’s forgotten among the last couple seasons of disappointment, but Oswalt was as good as the last decade had to offer.

Bob Levey

The baseball world lost their second stellar Roy this winter when Roy Oswalt announced his retirement. It's fitting that the pair of Roy Halladay and Oswalt finished their careers within the same off-season, though, as they were two of the great arms of this century, with Halladay seeing his career resurrected starting in 2001, and Oswalt making his major-league debut in that same year.

Halladay has already had his retrospective, but invoking his name makes sense, considering the two are all of a year apart in age, and sit one and two on the ERA+ leader boards, minimum 2,000 innings, from 2001 through 2013: Halladay at 138, and Oswalt at 127. They're two of just 18 pitchers to throw at least 2,000 innings in that stretch, and even if you relax the thresholds a bit to 1,500 frames, Halladay comes in second and Oswalt fourth, with the latter tied with the likes of Justin Verlander, Felix Hernandez, and Chris Carpenter: Roy Oswalt, before the last few years when it looked like he should have hung it up, was fantastic on the mound.

Oswalt also ranked fifth in pitcher wins above replacement, according to Baseball Reference, from the start of his career through its recent finish, behind only Halladay, CC Sabathia, Mark Buehrle, and Johan Santana. Before health issues sapped him at the end, Oswalt averaged 208 innings per season over a nine-year stretch, and posted a 133 ERA+ in that time that many failed to notice or forgot about entirely if for no other reason than that the Astros were awful or mediocre for parts of it: while the Astros made the playoffs three times with Oswalt on the roster, they only finished first in his debut season, and didn't make the playoffs anytime after 2005, just a few years into his career.

This lack of recognition extended to hardware, with Oswalt never finishing better than third for the Cy Young, with six different finishes in the top six for the award. What makes this odd is that, on top of his durability and success through more advanced pitching stats, Oswalt also had plenty of seasons where he dominated in the more traditional figures that sometimes inform award campaigns. He led the National League with 20 wins in 2004 while also leading in games started -- a feat he achieved twice in consecutive years with 35 starts in each. He led the Senior Circuit in ERA at 2.98 in 2006, a year after popping a 2.94 mark with 20 victories, and finished fourth in the voting in each season. It was a matter of being in the wrong place at the wrong time for Oswalt, as he lost to Brandon Webb -- a pitcher who could very likely have been the actual best of this century if not for career-ruining injuries -- and Carpenter, who was every bit Oswalt's equal at his own best.

When you combine a lack of media attention to Oswalt with relative obscurity pitching for an unsuccessful franchise during the second half of his career, and then pile on top of that his poor performance over his last two seasons, you end up with Oswalt quietly retiring and ending a career that deserved more appreciation. Like with Roy Halladay, Brandon Webb, Chris Carpenter, and maybe Johan Santana as well -- depending on how his attempted return goes -- Oswalt is yet another pitcher who has dominated this century, but has also seen his career end far too soon, before his achievements and greatness could settle in. That’s a shame, but at this point, Oswalt is probably used to being overlooked.

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