Believe it or not, most of our writers didn't enter the world sporting an address; with a few exceptions, they started out somewhere else. In an effort to up your reading pleasure while tipping our caps to some of the most illuminating work being done elsewhere on the internet, we'll be yielding the stage once a week to the best and brightest baseball writers, researchers and thinkers from outside of the BP umbrella. If you'd like to nominate a guest contributor (including yourself), please drop us a line.

Matt Kory is a former Urban Planner turned stay-at-home dad. He exists in a whirling vortex of crying, poopy diapers, and sports, punctuated by daily columns at Over The Monster. He also writes for the online magazine Splice Today. He hopes to one day make a living from doing this stuff, so feel free to contact him at and tell him what a genius he is. In his spare time he does not enjoy jogging, sleeping, more crying, or being scratched by his cat. He lives in Portland, Oregon with his wife and two three-year-old boys. Follow Matt on Twitter at @MattyMatty2000.

Roy Oswalt had a plan. Roy Oswalt is a free agent. Roy Oswalt is a pitcher. Roy Oswalt is breathing. Roy Oswalt was going to cash in. Roy Oswalt knew that. Roy Oswalt’s agent knew that. We all knew that. It was common knowledge.

All of Oswalt’s fellow pitchers were getting paid. Mark Buehrle got so much money from the Miami Marlins that he’ll be able to pay opposing batters to strike out if he can’t strike them out himself. C.J. Wilson got so much money from the Los Angeles Angels of Anaheim* that he’ll be able to buy every ticket to all the shows on an entire Arcade Fire tour. Then he’ll buy Arcade Fire. Then he’ll start his own chain of arcades and light them on fire (without fear of reprisal, because if Donald Trump has taught us anything, it’s that rich people can do whatever they want). 

* Los Angeles Angels of Anaheim anagrams to 1) A Manganese Gene Fools Shill and 2) Neon Hos Smelling A Leafage. It should be noted that I have provided this information to you at no further cost.

Even the Triumvirate of Mediocrity that is Chris Capuano, Aaron Harang, and Bruce Chen got two-year contracts. Sure, two of those contracts came courtesy of the Dodgers, who were last sighted trying to buy real estate in Greece with Icelandic krónur, but it seemed the market was ready to pay Roy Oswalt.

Even the second-worst-case scenario* for Oswalt was a two-year deal at good money in a place he wanted to pitch. Or so we thought.

* The worst-case scenario for Oswalt involved a fish, a sock, a light bulb, an overheated pan filled with cooking oil, and a straitjacketed Weird Al Yankovic. Suffice it to say this was unlikely.

Just before free agency Oswalt met with his agent, Robert Garber, to discuss his impending free agency.

October 29th, 2011
Robert Garber: Great to have you here, Roy. Might I offer you coffee, a latte, a steamer, or a caramel macchiato? 
Roy Oswalt: You might.
Garber: [pause] … okay. So, Roy, we’re here to discuss your impending free agency. We think you can cash in. Hard.
Oswalt: Hard, huh?
Garber: Hard. You’re going to get years, dollars, and your choice of location. So, yes, hard.
Oswalt: How hard?
Garber: Hard! Extremely hard.
Oswalt: Can you give me some bad similes?
Garber: Oh, sure thing. You’re going to cash in as hard as The Rock’s pectoral muscles. As hard as tying your shoes after drinking 27 wine coolers. As hard as calling yourself a man after drinking one wine cooler. As hard as it is to understand who is writing this garbage and how they ever managed to sneak past the editors and onto these virtual pages in the first place. As hard as… wait, what are you doing?
Oswalt: [typing on phone] Oh, don’t mind me, I’m just getting a new agent.

* * *

A month went by. Then another. The big names started to come off the board as Wilson and Buehrle signed. Then the aforementioned Triumvirate of Mediocrity Harang/Chen/Capuano all got their golden tickets to the Wonka factory. (You just know Capuano is going to chew the experimental gum and turn into a giant blueberry.) Rumors started to spread saying Oswalt might sign for fewer than the three years he was previously reported to be seeking.

Just before the holidays, Oswalt’s agent got a call from a baseball reporter wondering why Owalt had yet to sign or, indeed, be seriously connected with any team.

December 20th, 2011
Garber: Hello?
Irritating Reporter: Hi Roy, this is Irritating Reporter.
Garber: Hi, Irritating Reporter, how can I help you?
Reporter: How is it going with Roy’s free agency?
Garber: It’s going really well!
Reporter: [writing]
Garber: Roy is very much in demand.
Reporter: [writing]
Garber: He’s had tons of great multi-year offers from some great teams.
Reporter: [writing]
Garber: We’re very excited. It’s going to be a difficult choice for Roy.
Reporter: [writing] Thanks!
Headline: Oswalt Totally Screwed! Will Accept Anything From Anyone At Any Time!

* * *

Somewhere past New Years, Oswalt and his agent began to try to nail down some options. Oswalt was interested in the Cardinals, so his agent gave St. Louis GM John Mozeliak a call.

January 15th, 2012
Garber: We’re looking for something in the three-year, $30 million area.
John Mozeliak: We can give you the years, but we can’t give you that money.
Garber: What can you offer, then?
Mozeliak: A dollar.

* * *

Oswalt was also intrigued by the idea of joining the Rangers, so his agent put a call through to Jon Daniels. Daniels wasn’t in, but his call was returned shortly thereafter.

January 16th, 2012
Garber: Hello?
[unlisted number]: We love Roy! Love him! I’m calling to personally offer him eight years and $150 million. He can have two suites on the road, unlimited use of the mini-bar, a first class seat for his poodle, Mr. Pickles, a poodle named Mr. Pickles, and I’ll even throw in a conjugal visit per year.
Garber: That’s gross, Mr. Hicks. Please stop calling me.

* * *

One team that Roy Oswalt did not want to play for was the Red Sox. Boston’s GM Ben Cherington was interested in Oswalt, however, and Cherington put in a call to the free agent pitcher’s agent to discuss the prospect of joining the Red Sox rotation.

January 21st, 2012
Garber: Hello?
Cherington: Hello, this is Ben Cherington, GM of the Red Sox. We’re very interested in bringing Roy to Boston and would like to extend an offer of…
Garber: Ha ha! Got you! Please leave a message after the beep.

* * *

Later, Cherington tried again, but his attempts at persuasion were not successful.

January 25th, 2012
Cherington: What can I do to convince you Boston would be a great place for Roy to continue his career?
Cherington: Are you giving me the silent treatment?

* * *

Oswalt was receiving interest from teams he wasn’t interested in joining while the teams he wanted to play for were ignoring him. To counteract this unfortunate trend, his agent tried to drum up interest by taking the message to the people. First he tried Arlington, Texas.

January 28th, 2012
Garber: Roy Oswalt is a great pitcher! He has a 3.21 career ERA and has received Cy Young votes in more than half of his 11 seasons! He deserves at least $30 million!
Police Officer: You need a park permit for that megaphone out here, buddy.

* * *

After paying the fine, Oswalt’s agent took his show to St. Louis.

January 30th, 2012
Garber: I’m telling you, Oswalt is a great fit here in St. Louis.
Lady at bus stop: Who is Oswalt?

* * *

After improving Oswalt’s stock with what can only be described as a hugely successful public relations campaign, Oswalt and his agent returned to the bargaining table looking to strike a deal. First they met with Jon Daniels back in Arlington.

February 3, 2012
Garber: Look, Roy wants to play for you, Jon.
Jon Daniels, Texas Rangers GM: That’s great, Robert, but we just don’t have the room.
Garber: Roy is willing to be the number four or five starter, John.
Daniels: We’re already set there, Robert.
Garber: OK, the number five starter then.
Daniels: Sorry, we love Roy, but we just don’t have the need.
Garber: He can back up left field.
Daniels: [laughs] No, we’re pretty set there, thanks.
Garber: He’s willing to do some catching…
Daniels: We’re good at catcher too, thanks.
Garber: You didn’t let me finish. He’s willing to do some catching in the bullpen. He’ll sell some cotton candy between innings, and when you guys play in Milwaukee he’s told me personally he’s willing to be the Italian Sausage.
Daniels: I don’t…
Garber: Fine! The Chorizo!
Daniels: I can’t…
Garber: Listen, before you say another word, let me ask you one final question.
Daniels: Sure.
Garber: How clean are your urinal cakes?

* * *

Then they traveled back to St. Louis for another word with John Mozeliak.

February 5, 2012
Garber: Look, Roy wants to play for you, John.
John Mozeliak: Sounds good. We’re interested. What were you thinking in terms of a contract?
Garber: Well a major-league deal for…
Mozeliak: Security!
Garber: Hey! Ow! Hey! Get off me! What are you doing with my pants?

* * *

Things got a bit desperate…

February 12, 2012
Medium: OK, we’re going to hold our hands together and… yes, I can sense the spirits in the room. The spirit world has opened up to us. Now, again, who do you want to make contact with?
Garber: George Steinbrenner.
Medium: I am attempting to contact… George Steinbrenner!
[a ghostly apparition appears]
Woman: Hello?
Medium: You’re not George Steinbrenner.
Secretary: No, I’m Mr. Steinbrenner’s secretary. Who shall I say is calling?
Garber: This is Roy Oswalt’s agent.
Secretary: OK, I’m going to put you on hold. [click] Mr. Steinbrenner, there’s a Mr. Agent to see you.
[a second ghostly apparition appears]
Steinbrenner: Agent, huh? Right, right. Well send him in. Oh, and freshen this up for me, will you doll? [he hands her a full glass of water with a dead goldfish floating in it]
Garber: [leaves]

* * *

It is now February 14th. Roy Oswalt is still a free agent. Roy Oswalt is still a pitcher. Roy Oswalt is still breathing. Yet Oswalt hasn’t cashed in. These things are always hard to nail down from the outside (see “Fielder, Prince” for the latest example) but teams who want Oswalt—and at this point that is primarily the Red Sox—aren’t willing to spend to get him, while the teams he’d consider playing for are willing to spend even less.

This makes some sense when you consider that BP’s injury database lists seven different back injuries for Oswalt dating from August of 2009.

Quick Quiz: A pitcher with a bad back is like…
A) A waiter with a bad memory
B) A hairless cat
C) An ugly baby
D) All of the above
E) I am a sad clown

Of course the answer is D, all of the above, though there is some truth to E as well. Now Roy Oswalt will either have to sign with the Boston Red Sox, which he doesn’t want to do, or accept whatever pittance the Cardinals offer in order to enjoy the warmth and hospitality of the great city of St. Louis, which, I hear, has an arch. Roy Oswalt likes arches.

If I have to predict what will happen, and I don’t, I’ll say that Roy Oswalt will sign with the Cardinals. In July, after all of Boston’s starting pitchers are injured in an unfortunate merry-go-round accident, Boston will trade for Roy Oswalt. Roy Oswalt will pitch for the Boston Red Sox. The universe will laugh. The universe hates Roy Oswalt. 

Thank you for reading

This is a free article. If you enjoyed it, consider subscribing to Baseball Prospectus. Subscriptions support ongoing public baseball research and analysis in an increasingly proprietary environment.

Subscribe now
You need to be logged in to comment. Login or Subscribe
Weird. Entertaining as hell, but still weird.
I'll take it. Thanks.
Brilliant stuff, Matt. The kicker could be Roy starts the wild card playoff game at Fenway. But in what uniform ?
That's very kind of you. I don't think there's much chance he ends up in Boston. Unless that is literally the only offer he has. So if he starts any games at Fenway he'll be wearing the road uniform.
Nicely done, Matt.
Thanks, Marc!
That was a fun article. Thanks!

Oswalt will play for (insert team here with first major pitching injury).
I'll guess he ends up in St. Louis. That's where he wants to go and they have the need. I think they'll figure out a way to make the money work. Eventually.
I would read this guy everday. Hire him.
I'm just glad you weren't minused to oblivion.
me too good stuff
This is fantastic.
You're just saying that because Matt is fantastic.
Oh, you guys!
That was the worst Sloth impression ever. You're supposed to say '_Hey_ you guys!'

Question being, why not the Sox? Outsize expectations for the team even in another Bridge Year? Facing ridiculous lineups night in and night out? Wicked awesome fans? Dearth of fried chicken? Too far from Mr. Pickles?

Not saying that there aren't 100000000 good reasons, just wondering which you think is most salient.
Well, Mr. Pickles is clearly an important factor, but if you're asking me, and I sense that you are, I'd say the Red Sox have made their interest in Oswalt known. If Oswalt wanted to play in Boston I imagine it would've happened by now. It hasn't though, so I take that to mean it's unlikely to happen. That all said, the fact he hasn't signed elsewhere still means it's possible he wears a Boston uniform this season.
Mr. Kory, do you have the transcript of the conversation where Oswalt turns down a one-year, $9 million dollar deal from the Tigers? (Reported on Hot Stove/MLB Network, 02/13/2012)
It would probably go something like this:
That clip just totally made my morning--and you're right--that probably was his reaction.
This guy has to go. I can't read this stuff at the office without laughing out loud.
Nothing more pathetic than the authors posting in the comment section how brilliant the guest writer is.

Thank you for wasting my time reading a 'Hey look at me, aren't I clever, did you see what I did there' column about nothing.

It is SAD how far BP has fallen.
This is one of those articles you either love or hate. I'm fail to see the value added as well, but its nice to have the variety.
"* Los Angeles Angels of Anaheim anagrams to 1) A Manganese Gene Fools Shill and 2) Neon Hos Smelling A Leafage. It should be noted that I have provided this information to you at no further cost."

Shameless attempt to appeal to the dianagram demographic.. I love it :)

Interestingly, Neon Hos Smelling A Leafage anagrams to Los Angeles Angels of Anaheim. But Diane knew that.
Outstanding. Just wait until Roy hears that the Angels and Indians (real, actual, non-Pirate baseball teams) are considering AJ Burnett. Have they called Roy? If not, how does that make Roy feel?
The Pirates are pursuing Burnett more than anyone is pursuing Oswalt... :P
That's a great point. Why spend... well, anything on AJ Burnett when Oswalt is out there? Of course, Pittsburgh could have contacted him and maybe Oswalt doesn't want to play there which would be both unsurprising and a given considering Oswalt's off season to date.

(And thanks.)
Reminds me of that old joke...

Grand Prize: One week in Pittsburgh
Second Place: Two weeks in Pittsburgh
Really good. Something that we don't see enough of in BP - humor. While I read just about every column presented, I see a tendency to take this all a bit too seriously. This IS baseball for heaven's sake, not rocket-surgery.
Thanks for the kind words, but I think BP has done a great job of incorporating humor into the site. Everything Sam Miller writes is hilarious, Jason Parks, Ben Lindbergh, Jay Jaffe and Steven Goldman are all very funny, and now the Platoon Advantage people are going to be writing here as well, and that's just off the top of my head.
Don't forget Ken Funck's funniness too :)

Rats. I knew I'd forget someone.
Rocket-surgery is not as difficult as they make it out to be, thankfully.
Any chance he goes to the White Sox? It's not too far from St Louis or TX or AL or wherever he prefers to be. Sox could use the arm although the Cubs maybe more so.
You never know with Kenny Williams. And Chicago is much closer to his home than Boston or Philadelphia. It could happen. Why it would is a whole different inscrutable kettle of fish, but it could.
this was an excellent piece. i feel bad for everyone that always need to absorb "value-added" content. lighten up, grab a fresca.
Thank you. It sounds obvious to say, but not everything is for everyone. Fortunately has BP done a great job by featuring lots of different types of writing. I'm just honored to be an infinitesimally small part of that.
Funny but I don't think you fully captured Oswalt's ambiguous feelings about playing vs his family. We saw that in Philly when he insisted on running his own tractor to help out his parents after a storm. Later he talked about retiring. Baseball just is not that important to him.