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Come Fan with UsSaturday, June 27, 2026

Roy Oswalt retires to the Hall of the Almost Famous

Roy Oswalt isn’t a Hall of Famer, but he was one of the very best pitchers in the National League for a long time.

The last time an Astros great retired, we took a little time to ask if he was a Hall of Famer. Consensus: maybe he was, but he probably wasn’t. At least, it’s still an open question.

Roy Oswalt announced his retirement on Tuesday. There is no surprise or mystery with this one. He is almost certainly not making the Hall of Fame.

There are pitchers worse than Oswalt in the Hall of Fame, sure. There are worse pitchers who get significant support for the Hall, too. He’s a much better choice than, say, Jack Morris, to pick a pitcher totally at random. It wouldn’t be distasteful if he were in, not at all. Unless I’m underestimating the leniency of the whatever they’re going to call the Veterans Committee in 2030, though, Oswalt isn’t getting in.

It’s here, then. It’s a personal milestone. Oswalt is the first Hall of Nearly Great player whose career I followed from prospect to retirement. If you’re older, you’ll know what I’m talking about. If you’re younger, you’ll get there. Oswalt is my guy.

A lot of my baseball-card memories involve opening packs and quickly sorting cards into two piles. The good players went into one pile, and the commons went into another. In that pile of good players were players like Frank Viola, Jimmy Key, and, yes, Jack Morris. As I got older and started paying more attention to baseball, it kind of surprised me that those guys weren’t Hall of Famers. It took a while to figure out what a Hall of Famer was. If not Dave Stieb, then whom?

It took a bit to figure out. But by the time I was in my early 20s, well past my card-collecting days, I had a decent idea of what a Hall of Famer actually was. And I didn’t even need WAR, you dorks. Just a lot of Bill James books.

Around that time, an undersized right-hander was tearing up the Texas League. He wasn't a top-100 prospect before the season. He wasn't a top-10 prospect for the Astros before his breakout year. There he was, right below Eric Ireland and Jeriome Robertson.

When he came up, he was excellent right away. There wasn’t an is-he-or-isn’t-he stage. Most young pitchers wobble around like a newborn giraffe, barely staying on their feet, giving up runs and slick with something awful. Oswalt was spared. He was one of the best pitchers in the National League from the moment he put on an Astros uniform.

The season after that, Oswalt was one of the best pitchers in the National League.

The season after that, he was one of the best pitchers in the National League, though he missed some time with injury.

The season after that, he was one of the best pitchers in the National League.

The season after that, he was one of the best pitchers in the National League.

The season after that, he was one of the best pitchers in the National League.

The season after that, he was one of the best pitchers in the National League.

The season after that, he was one of the best pitchers in the National League.

He was spotty for a season after that, but he came back to be one of the best pitchers in the National League in the following season. And while all these seasons are going on, they’re long. You spend them examining and reexamining everything you think you know about baseball. You’re impressed by prospects that make the leap toward stardom, and disappointed by veterans who fade away. Good teams become bad, and bad teams become good. The prospects-turned-stars turn into players impossible to evaluate.

The whole time, Roy Oswalt is one of the best pitchers in the National League. He’s a constant, someone you don’t have to think about.


(Photo by Bob Levey/Getty Images)

Now, he was never the best pitcher in the National League. He made three All-Star teams, but so did Barry Zito. Oswalt finished in the top-five of the Cy Young voting five times, but he never won it. It’s this difference between “best” and “one of the best” that will keep Oswalt on the Hall of Fame ballot for a few years but out of Cooperstown.

There was always an unfamiliar name that came up in baseball chats with older friends and relatives. Something like this:

“Jerry Koosman. Now that was a heckuva pitcher.”

And I’d think, oh. I didn’t know anything about Koosman, so I’d have to play along. Then when I got to look at his Baseball-Reference.com page, my goodness. He was, indeed, a heckuva pitcher. That goes for Frank Tanana and Jim Kaat, John Candelaria and John Smiley, Billy Pierce and Vida Blue. There are a lot of pitchers who were great for extended periods of time, but just not great enough for long enough to get in the Hall.

It took Roy Oswalt to make me realize exactly what it was like to follow one of those pitchers from prospect to pensioner. It’s weird. He was good for so long. He was more talented than almost anyone who came before, and he’ll have a better career than almost anyone who will come after.

Oswalt makes you realize just how danged hard it is to be a Hall of Famer. Which is sort of the point of the Hall of Fame. But even without the plaque, he’s still one of the best pitchers I’ve ever watched. And in 20 years, some brat will be chatting me up about Roy Oswalt, and I’ll mumble something over my scotch, like:

“Roy Oswalt. Now that was a heckuva pitcher.”

He really was, you know. He really was.

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