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Prospect Retro Redux: Roy Oswalt

More photos » Bob Levey - Getty Images

Roy Oswalt of the Houston Astros throws against the Chicago Cubs in the first inning at Minute Maid Park on June 5, 2025 in Houston, Texas. (Photo by Bob Levey/Getty Images)

Per Reader Request, here is a look at Roy Oswalt of the Houston Astros, his development as a prospect, and his historical standing.

Star-divide

I did a Retro of Oswalt in 2005, and of course the historical background remains the same.

 

 

Roy Oswalt was drafted by the Astros in the 23rd round in 1996, from high school in rural Mississippi. Scouts were aware of his arm strength, but many teams were skeptical about him since he is not a tall pitcher. He went to Holmes Community College, then signed as a draft-and-follow the following spring. He made his pro debut in '97, going 1-1, 0.64 in 5 starts in rookie ball (28/7 K/BB in 28 innings), then 2-4, 4.53 in 9 starts in the New York-Penn League (44/15 K/BB in 52 innings). This was before I did much work on short-season players, and he was not in the '98 book. Retrospectively, I would have given him a Grade C or C+ due to his K/BB ratio.

Oswalt split '98 again between the Gulf Coast League and the NY-P, and again he pitched well. He went 4-5 but with a 2.18 ERA in 11 starts for Auburn, with a 67/31 K/BB, allowing only 49 hits in 70 innings. I put him in the book, without a letter grade, but with the notation that he could "come on real quick" in '99.

He did just that, going 13-4, 4.46 in 22 starts for Class A Michigan. Now, you look at the 4.46 ERA and think "that's not that great," but in this case his W/L record was actually more representative of how well he pitched. He posted a strong 143/54 K/BB in 151 innings. I gave him a Grade C+ in the '00 book, but again praising him as a sleeper to watch.

Oswalt broke through in '00, starting off 4-3, 2.98 in 8 starts for Class A Kissimmee, then going 11-4, 1.94 with a 141/22 K/BB in 130 innings for Double-A Round Rock. "Buy Roy Oswalt stock," I wrote in my book for '01, giving him the coveted Grade A rating and ranking him as the ninth-overall prospect in the game. Among RHP prospects, I ranked him 4th, behind Ben Sheets, Josh Beckett, and Jon Rauch.

Oswalt began '01 in Triple-A, posting a 34/6 K/BB in his first 31 innings and earning a trip to Houston, where he went 14-3, 2.73 in his Major League debut. He has been one of the best pitchers in the National League ever since.

 

 

We now have an additional five years of data to look at. Looking at comparable pitchers, here are some names through age 31.

SIM SCORES: Roy Halladay, Tim Hudson, Mike Mussina, Bret Saberhagen, John Candelaria, Don Newcombe, Jim Maloney, Bob Welch, Dizzy Dean, and Andy Pettitte.

PECOTA Comps: Freddy Garcia, Jon Lieber, Kevin Millwood, Bronson Arroyo, John Smiley, Mike Boddicker, Jimmy Key, Charlie Liebrandt, Doug Drabek, and Ted Higuera.

Comps are all over the map, with the Sim Score list looking more impressive and, I think, more accurate. Everyone on this list was a fine pitcher (at worst), though their styles differed greatly.

Oswalt currently stands at 142-78 (.645), 3.22 ERA, 135 ERA+, with a 1562/436 K/BB in 1896 innings so far, 1832 hits allowed. Currently 32 years old, he is about 40% of the way to a Hall of Fame path. His "Black Ink" total is 13; an average Hall player finishes at 40.  Gray Ink is 112; the average HoF is 185. His Hall of Fame Monitor rating is 55, with an average Hall guy at 100. Hall of Fame Standards rating is 33, with an average Hall rating of 50.

If Oswalt can remain active for another five or six years at his current level of effectiveness, he'll be in the Hall conversation although not a sure-fire guy. If he fades too quickly, he'll fall short, although will still rank as one of the best pitchers of the early 21st century.

He was one of the most successful examples of the now-defunct "draft and follow" process. Note that it took $500,000 for the Astros to sign him back in the spring of ‘97, which was supplemental/early second round money back then. If he had re-entered the draft pool for ‘97, his stock with scouts was high enough for him to earn the bonus as a much earlier pick. He is also another data point indicating that "short" right-handed pitchers can indeed be quite successful, provided they have the requisite arm speed and athleticism.

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Trade Reactions, Part Two

Aug 2010 by John Sickels - 1 comment

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I've always been a fan of Oswalt's

It seems that he was often overlooked b/c of his size, and where he played.

I wouldn’t call him Hall of Fame caliber, but an excellent to solid pitcher for quite sometime.

I do question his effectiveness if he gets dealt to the AL midseason this year though.

2010 Tigers contracts coming off the books:

Maggs (18M)
Willis (12M)
Bonderman (12.5M)
Robertson (9.5M still being paid this year)
Inge (6.6M)
Damon (8M)

2011 is the year of the Tiger!

by sportznut3081 on Jun 23, 2025 12:35 PM EDT reply actions  

He could have been a lot better

I was a big fan of the Wizard when he got called up, but he has never struck me as a “bulldog” type competitor on the mound. Maybe he’s calm and collected on the inside and a fierce competitor on the inside a la Jeff Bagwell.

He doesn’t come across as someone who loves the game, but does it to get paid. Always talks about retiring at a young age (at the end of this contract) and not sticking around to see what kind of legacy he will have. Just wants to hang out on his ranch in Mississippi and hunt and fish. Nothing wrong with that, but doesn’t make him very endearing to the fans.

by Raidas77 on Jun 23, 2025 1:15 PM EDT reply actions  

Thanks John.

I’ve liked Oswalt for a long time now. Great writeup.

Baseball makes the world go 'round, or at least in my world it does.

by Whiteyballer on Jun 23, 2025 1:51 PM EDT reply actions  

Why Do Prospect Retros That Have Been Completed

When there’s no minor league stuff to add on. This is a minor league site, let’s ACTUALLY talk about the minor leagues. The retros are the worst articles on this site.

My Guys: Gillies, Pacheco, Drabek, Verlander, Ozuna, A Salcedo, S Rodriguez, and others.
BriGay'd Fo Lyfe.
New Minor League Site Soon!

by cwhitman412 on Jun 23, 2025 4:19 PM EDT reply actions  

I actually like them

It gives me a reminder that not every star tears it up in the minor leagues, or is drafted high. Shows that they can come from all backgrounds.

by Tex2044 on Jun 23, 2025 4:28 PM EDT up reply actions  

retros

They are the most frequently requested pieces.

I’ve been doing a lot more minor league notes this year since it is, after all as you point out, Minor League Ball. But I’m also an historian, and I think we can learn from the history of players and how they developed.

by John Sickels on Jun 23, 2025 5:17 PM EDT up reply actions  

Retros kick ass,....

whining doesn’t.

by SenorGato on Jun 24, 2025 12:39 PM EDT up reply actions   1 recs

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