Roy Oswalt is a celebrated Major League pitcher who has spent his entire nine-year career, thus far, with the Houston Astros. He’s won almost twice as many games as he’s lost (137-70) and has compiled an impressive 3.23 career ERA. He’s won 20 games twice – in the 2004 and 2005 seasons – and has played in three all-star games. Roy is in contention for the Cy Young Award seemingly every year, finishing in the top five for Cy Young voting year after year.
So, Roy, what was your first car?
It was a ’63 Step Side truck. I worked all summer to get it. It was a bad green. We got a guy to paint it for me for $500. He did a pretty good job, too. Painted it blue. I drove that until my senior year and got another Step Side Truck – a ’95. I’m looking for that truck – the ‘63.1 have the serial number and everything. I’m trying to go through the state where you can send in and they’ll see if you’re looking for it for real or looking for someone. They make sure you want to find it. I just want to restore it.
I have other athletes in the book that have located a car from their past. David Ragan, for instance. There was an old Corvette his dad had sold to get funds to help David in his early racing days and he found it in Pennsylvania. The guy didn’t want to sell it back and David wanted to buy it to surprise his dad. I guess David sweetened the deal and he finally got it.
It’s actually funny, 10 years after I sold it, I was walking through the woods and the truck drove by and I couldn’t get back to my truck in time to catch it, and that was it. I wrecked the ’63 one time and tried to Bondo it myself. I noticed the Bondo when it drove by. That was probably eight years ago when I saw it. I sold it 13 or 14 years ago.
What did you own after that? Cars, trucks tractors, bulldozers?
When I was drafted after college, I bought a boat – a splash and sea kind of boat I used to tow around the city. We had fun with it. I had that for three years. I towed it around from New York to Michigan to Florida and all across the country. Then I sold it and I bought a ’98 Explorer in 2000. Now I have a Cadillac Escalade I bought in ’01 when I got to the major leagues. I got another Cadillac Escalade last year for my wife. And I have a ’63 Chevy Camaro and a 2010 Tundra.
Tell me about the Bulldozer that you have.
The best thing I own. (GRINS FROM EAR TO EAR) The restaurant I own, I actually made that parking lot with it. I got it for winning a game in the World Series in ’05. The owner of the Astros has a lot of real estate in Texas and he bought a bulldozerto clean up his ranch. I asked him what he was going to do with it when he was done and he said, probably sell it. I was going to buy that one from him. We were in the playoffs and I was watching Tate on the St. Louis Cardinals before I pitched against him. The owner came in and we were talking while I was watching Tate on TV, and he said he’d buy me a new bulldozer if I beat Tate. I got up, shook his hand and went back. I remember pitching about the sixth inning and we were winning 4-1.1 was thinking I needed four more innings. I got through three more innings and the reliever came in, in the ninth, and finished it off. I never left the field. I sat in the clubhouse next to the owner and reminded him of it, and he came through. I got it in the off-season.
What kind of music do you listen to in the car?
All kinds of country – Kenny Chesney, Merle, Hank, Rascal Flatts.
Have you ever looked at another player’s car and told yourself you needed one of those?
I am not big on new cars. We have a lot of guys that have Lamborghinis and stuff, but I’m not big on them. I like older cars. We have a first base coach – Cheo Cruz – that played with the Astros for 20 years. He had a ’57 Chevy that was nice and he also had a ’64 Mustang that was a convertible. That was nice. I like old, classic cars.
They’re hard to beat. What about your Camaro? Tell me about how you found it and the restoration process.
I was actually in Texas. I love ’67 and ’69 Camaros. Probably ’69 the best. I was looking at one that was pretty close to the original, something I liked. It was nice on the inside. I like the old-school look with a new school ride, so I was going to keep the look on the outside, but have the drive and suspension of a new Corvette. I took the inside of a 2010 Camaro and put it in the ’67 Camaro.
Do you get a lot of tickets?
Something was definitely up here. I wasn’t going to leave it at that.
Do you get pulled over a lot?
I’ve had a few tickets.
How fast have you gone?
Well, actually, I wasn’t driving. I was 15 and I just had a permit, but my friend had his license and we borrowed a car from a friend. She was 19 and the car was a new Accord with about 500 miles on it. There was a town up the road about eight miles – we used to hang out there. We came driving through town in a new car
and everybody wanted a ride, so we picked up two girls and my wife-who I was dating at the time -and my brother and a friend of mine. So there were seven of us in a Honda Accord.
How did you manage that?
My friend, my wife and I were sitting in the middle. My brother and two girls and another guy were in the back. We decided to go to another town and shoot some pool, and we wanted to see how fast it would go so we floored it.
Was it a four- or a six-cylinder?
It was a six. We probably got it to about 120. It wouldn’t go any faster. We were on a straightaway, and back then they wouldn’t let cars cut off. Now, they run too fast, they’ll blow up. We get to the top of the hill and there’s a State Trooper. All I see is blue lights. At the time, my buddy told me he had a license, but he didn’t. He had a permit. I had a permit. My brother had a license. So my buddy’s legal, but he only has a permit. He says, ‘What do I do?’ I said pull over and he said he wasn’t stopping. So we don’t stop and that policeman chased us for, it seemed like days, but it was hours. We had that thing floored.
This is like an episode of Dukes of Hazzard.
Yeah. We’re flying down the road. We can see blue lights two hills behind us as we go up a mountain on a dirt road. The car’s turning so we decide, whichever way the car goes, we’re going the other. There’s two dirt trails. Well, this car’s going 30 and we’re going 100, so there’s a little bit of dust. Then we get to a T, and luckily on the other side of the T is a field, and we’re, like, which way, which way and nobody answers. So we actually jump the T and head out into this field and I’m, like, ‘Right, right, right,1 and we turn right. We got so far ahead of him he called back-up and set a road block. But we’d taken so many turns, they didn’t know where to set the road block. We get back to the highway and there’s three cars. When we passed the officer, it was pitch dark so he couldn’t see the color of the car.
We got in between those three cars and as all this goes on, my buddy that has a license changes seats with my buddy driving because he doesn’t want to get in trouble with his permit. We ease up to the road block and they have Mustangs ready to go. We pull up with a car in front of us and a car behind us. An officer comes up and asks to see a driver’s license. He says, ‘What are you guys doing down here?’ My buddy says, ‘We had to take this girl back home after we went to the movies. What’s going on?’ Like we have no idea. The officer says, ‘Somebody’s trying to be funny and outrun the law.’ The police officer gave him back his license and we drive through the road block. We’re free and laughing all the way home. Three days later, the guy that turned at the top of the hill got video.
Yeah, and they got the tag number. They went to the girl’s house. We dropped the car off that night and I know that thing had dings and scratches on it. We washed it up, but it was dark and we couldn’t see. She’s, like, ‘You guys are so responsible. Anytime you want it, you come get it.’ I felt bad. Three days later, the cops come to her house to arrest her. She told them who did it and called Scott, my friend, and said, ‘Get ready, the cops are coming to your house.’
They showed up. He got a lot of tickets and stuff, and we all got in big trouble.
Did you get grounded? Did you get a whoopin’?
I didn’t get a whoopin’, but I got grounded for a while.
Wow, that’s a great story. That has to be one of the best that I have heard. Rules are made to be broken!
Until my kids read it.
Okay. It’s a great story, though. I have to print it. But maybe we should move on. When you got your first big contract did you go out and buy a cool car?
I actually didn’t. I was scared I wouldn’t make the big leagues, so I put most of it back to build a house. I did, however, buy that boat.
With the Step Side Chevy, it seems that you are quite a Chevy guy. Is there a dream car or truck you have ever wanted or dreamt about?
Classic cars. I like ’57 Chevys. They were big cars growing up. My dad loved them and he would brag on them. Going down the street, if we saw one, he would always ask us what make, model and year.
Have you ever had any bad accidents other than outrunning the law?
I’ve had a few. I had one in high school. (A DEVILISH GRIN SPREADS ACROSS HIS FACE) I wasn’t supposed to be doing what I was doing. I was taking home a friend after high school who didn’t have a ride, after baseball practice. That ’63 truck I had, it had a six-cylinder when I got it and I put a 327 in it – an old Holley.
What’s up with you and this horsepower thing? You always need it bigger and faster.
It’s funny, when I stop at a light if they take off, I have to pass them. There’s something about competition. I have to beat them and race through town.
So, I take him home and he says something like, ‘This thing won’t run very fast.’ I take off and I try to go around this long curve and I let my right tire get on the gravel. We actually went down in one ditch, and went across and started spinning in the highway. As we’re spinning, it’s funny, it’s almost like slow motion. My buddy says, ‘We’re going to flip.’ I’m trying to drive and we start to straighten out. I shift into second and try and go the other way to drive out of it. I’m going so fast, backwards, smoke is coming off the tires. We go through and hit a fence post and end up in a pond. I get out and I think my truck is dead. The fender’s gone and I try and back it out. The tire actually had come off the rim when I came off the road and I couldn’t get it out. I had to call a tow truck and got grounded for that, too, because I wasn’t supposed to be down that way.
What year was this and how old were you?
Nineteen ninety-three, and 16.
So, Roy, why are you so rough on vehicles?
I like to try them out.
How well can you drive a stick shift?
That’s all I drive.
How many more years will you play? I ask because some athletes in this book are on the cusp and some are retired.
I’m going to play two more, for sure, and then decide. We’ll see where I’m at. If I’m close to something, I might go after it numbers-wise or championship-wise, but probably not much longer than that. I want to try and do something else, maybe NASCAR. I love competition.
Cool. Okay, road trips. Do you have any favorites.? I’m sure you drive from Texas to Mississippi.
Yeah, I own land in Mississippi. Actually, Jake Peavy, we own land together there and in Michigan, and we kind of hunt there and go to Illinois and hunt, and then Alabama, maybe, all season. It’s a tour.
So, your hunting ranch, is it like Jay Novacek’s hunting ranch. The Upper 84?
That’s what I have here.
Tell me all about it
I started it in ‘06.1 high-fenced it and I’ve been trying to get the deer to a high quality so somebody who would pay to come on will shoot quality deer. I just started selling hunts this year and had a few guys come on. It’s fun. A lot of these people are corporate people and I like meeting them. It gives you options after baseball. Plus, watching someone else kill one is as fun as hunting. The place in Illinois and Missouri is just personal, with friends and family.
Is it solid deer or are there other options for a good hunt?
I have some exotics too, from Africa and India.
How long does it take you to dress a deer?
Just take the hide off of it? Twenty minutes.
Tell me about your charity. Fund 44.
We have a bond set up, so if someone loses their house in a fire or they lose their job, we buy stuff at Christmas for them.
Tell me about your restaurant.
We just built it. I wanted a steakhouse close. I’m tired of driving 45 minutes to eat.
I figured that was your restaurant when I drove by it. Do you have frog legs on the menu?
Yes, we have frog legs, quail, a catfish buffet, but we specialize in steaks. All Angus. I try to buy the best. I looked all over Texas and I actually get meat from Buckhead in Atlanta. The biggest thing for me, here, I try and invest in quality, but here you have to have something you can afford. I could have the best in the world, but no one around here is going to pay $50 a steak. I’m trying to get the best quality that you can afford. It’s been working so far. It’s called Home Plate and we opened in November of 2009. □
Roy, without a doubt, had the most rural location out of the 40 athletes in my book. Something about the smell of game, cow shit and hot rides just takes me back to growing up in small town Texas. Floy’s Southern hospitality was addictive and inviting. Heck, he even left me drive his bulldozer!