Winn the Cowboy

(December 2021. I wrote this story for a contest on Vocal, a website for creators. There’s a potential $5000 prize, which kicked my ass in gear; you’ll notice I hadn’t really written a full story since 2018, because I got really busy with adventures and essays and philosophy and poetry and relationships and meeting amazing people and economic struggles honestly just living my life. But of course, eventually the Great American Novel needs to be made of stories, not just essays and poetry. This story was super fun to write, because I had a recording of a bit of my conversation with Winn, and had also taken notes after the ride of everything I remembered about him. He was a hell of a cool character, ‘a different kinda cat.’ To write this story I listened to the same few minutes of recordings over and over, painstakingly transcribing the dialogue in all its messy imperfect glory. It’s so real, and so funny. I love Winn. It’s a great example of the kind of characters and conversations you can have hitchhiking. Due to the wordcount of the contest, it will be a small part of a much longer story, the story of my recent hitchhiking trip from LA to Louisiana on my journey home to Massachusetts after leaving my bus in Arizona. That longer story is coming soon; for now, enjoy this juicy short story about Winn the Cowboy. You won’t be disappointed.)

The white pickup, pulled over 100 yards away at the beginning of the long frontage road, had been sitting there for a few minutes. It could mean one of three things: the guy was thinking about picking me up, thinking about murdering me, or thinking about something unrelated to me— me being the hitchhiker at the other end of the road. 

It was around 11:20 AM on November 14th, 2021, and I’d only had my thumb out for about 20 minutes. My friends from the commune had dropped me off in Tucson at 11 to begin my adventure across the country, because I was out of money and had promised my mom I’d be home in Massachusetts for the holidays. I’d scouted this particular hitching spot on Google Maps street view before leaving the commune— an excessively long frontage road eventually split and fed left into I-10 East. I had walked most of the way up the road towards the split, with my heavy blue pack on my back and my beautiful black and white puppy on an orange paracord leash. My focus was on the occasional car that drove up the frontage road toward the on-ramp; this was a great spot because the drivers would have tons of time to size me up, familiarize themselves with me, and decide to pull over. Also, there was plenty of safe room to slow down, without worries about traffic or being in anyone’s way. You gotta make it easy for them. 

Cars had been going by at a rate of about one a minute; on a wide-open Western road like this, I’d guess somewhere between 1 in 30 and 1 in 90 drivers would pull over for me; of course, that’s just guesses and averages, but averages won’t give you a ride; it’s always and only that one real person who will give you a ride. That’s why you gotta make eye contact with every driver as they come towards you, gotta find their human face within the windshield and hit them with the kind of easy smile that tells them you’re the freest guy in the world, gotta hit them with just the right vibe to break through their anti-homeless blinders and make them do a double take, Hey, that kid looks kinda nice, not scary at all… and then they’re looking at you again, and you do a cute little move, give em the thumb personally, show you’re animated, human, communicating, and that’s when you hook em, and they pull over, your eyes pulled over the human heart of a hunk of metal that can drive you across the country, and goddamn if that isn’t the best feeling in the world. 

It’s a funny truth about hitchhiking that you can get picked up faster on a ramp with a trickle of traffic than on a ramp with a constant flow. It’s as if the presence of other drivers around makes it easier to ignore the hitchhiker, since Hey, someone else will pick him up, it’s not my problem. Being in a group makes it easier to override human compassion, as many of history’s atrocities attest. Everyone else is ignoring them! But when it’s just you and the hitchhiker on a long on-ramp, you tend to care a bit more about what happens to that poor kid; right now, you’re the only person around who can give them a ride, and who knows when the next ride will come? 

The white pickup that had been parked at the beginning of the frontage road for a few minutes began finally to move again, slowly, towards the on-ramp. I gave my best hitchhiker smile, and it slowed down right in front of me. The window rolled down, revealing a large leathery man with lots of white facial hair. “Where ya headed, young lady?” he said, in the most wonderful accent I’d ever heard. He’d seen my beautiful long hair and assumed I was a girl.

“Headed east for Thanksgiving, where you headed?” One subtle safety rule of hitchhiking is that you should always ask the driver where they’re going, not vice versa.

When he heard my male voice, he adjusted quickly. “Well uh young man, I’m headed all the way to El Paso.” El Paso is about 4.5 hours from Tucson, 320 miles. That’s a hell of a good ride; that’s a good day’s work done hitchin right there.

“I’d love to go to El Paso! You mind if I take a picture of your license plate and send it to my mom?” The moment of truth. Could this guy be trusted?

He processed the question for a second, and gave a hearty laugh. “I never heard that before, that’s a good idea! You got a good head on your shoulders there cowboy. Go for it.” I took the picture, sent it to my mom, opened the passenger door for Waldo to hop in, then hopped in myself. Waldo settled into the backseat of the cab; it was his first hitch, and I was so proud of him.

The beginning of conversation when you hop in with a new driver is always such an interesting moment, the moment of near-contextless communication, of a beginning plucked out of thin air to get the ball rolling, the inlet to cascades of dialogue that can fill 5 or 6 hours with a new person. You learn a lot about someone in those first few minutes; I learned very quickly that Winn, Winn Hall, was a talker. Sometimes the hitchhiker has to put in a lot of effort to keep the conversation fresh, but not with Winn. I’m not sure exactly what the first thing he said was— it was probably a compliment like “cute pup,” followed by another comment about the license plate thing. I’d tell him what I tell everyone, that I’ve taken over 500 rides before, and that I’ve only had to turn down 4 people who wouldn’t let me take a picture of their license plate. We both agreed on what that says about human beings— over 99% are good people, and we shouldn’t let a small amount of bad actors kill the social trust that we need to live with one another. People are worth trusting. Right away it was easy to talk to him; he asked for my story, and I told him about how I fell in love with hitchhiking when I was 18, how I wanted to adventure around America and write the Great American Novel, how I left my school bus in Arizona, how he was the first ride I’d had since 2019 before the pandemic. He was tickled by that; he really liked me, saw something of himself in me; when I told him I was 22 he got to gushing about how much he admired what I was doing, said it made him feel a lot better about the future. To be honest, I couldn’t imagine a better first ride; Winn made me feel like the American Dream. And, he kept calling me ‘cowboy’ and ‘pardner’, which really knocked me out.

I turned the conversation back onto him as fast as I could; I’ve heard my own story too many times, and while hearing it appreciated so heartily was great, I wanted to hear a new story. That’s the beauty of hitchhiking; there’s always new stories. And boy did Winn have them. And not only did he have great stories, but he had a great way of telling stories; he told stories in the way someone does when they have too many stories to tell; whatever comes out comes out fast and can zigzag at a moment’s notice to something else just as interesting. Even better, he did the whole thing with the absolute, without-a-doubt greatest West Texas accent I could have ever imagined. You shoulda heard him say pecan, pistachio, southern Cullarudda, sit and set, El Paso; it wasn’t a slow southern drawl, it was fast, we were both pouring out as much information as possible. It had the slightest Mexican twinge spicing up the quintessential Texas Cowboy twang. El Paso, in particular, he said with perfect Mexican pronunciation.

He told me that he did this drive from Tucson to El Paso every weekend, that he’d worn this ol truck out on this drive, that he’d grown up around El Paso and Las Cruces and knew every inch of the drive like the back of his hand. He had been working on building his son’s new house, he was running the project, and all his subs, or subcontractors, really liked him. It was almost ready to ‘turnkey’; he’d been working hard every weekend to make up for time lost earlier in the year when he’d had a big fall and broken ribs. He told me a story of how a decade ago a mayor had screwed him out of a $30,000 bonus he deserved for building a Lowe’s under budget; Winn went to this guy’s house and confronted him; the guy didn’t back down, and Winn ‘beat the absolute fuck out of him’ with a sock full of butter, if I remember correctly. He felt bad about it, since he never got the money, and instead had to pay the guy’s hospital bills; he also had to serve time in Santa Fe prison. Winn talked a lot about how much he learned in prison, how many good guys were in there, how his extra commissary money made him a lot of friends, how well he treated his fellow inmates and how popular he was as a result, how he won over Mike the Murderer, how he gave his breakfast away every morning to a new podmate as long as they gave him the meelk, how everyone got him a present from commissary on Christmas in return, how they called him the Podfather. It was about here that I decided I had to record the conversation; I didn’t want to forget any details about Winn the Cowboy.

“… well one a them mothafuckers stole my socks. Stole two pair a socks. I got up the next morning I said ‘God dangit Mike, these motherfuckers stole my socks.’ He said ‘What?’ I says ‘They stole my socks.’ Well the next day, I got up, my socks were back at my bed, folded, and the portal guy came around the next morning, head looked like somebody took his face, and just but the, they beat the fuck out of him in the shower,” 

“Holy shit!” 

“about three of those guys, beat the fuck outta him in the shower, and he came the next morning, put my socks back and left me a note that said, he said, ‘Mr Winn, Sorry, this will never happen again.’” 

“Wow… wooooooowww! It’s so funny, the socks perfectly folded…”

After he got out of prison, Winn started makin good money again, and after he paid the mayor off he bought $1200 worth of Cup o’ Noodles and brought it to the prison for his pod. To this day he and Mike in Silver City talk once a month: “I made some good friends there. There’s some good fuckin guys in prison, just because they’re in prison doesn’t make them bad guys. So I’ve been around the fuckin horn to Matterhorn and back three times in my life, and I’ve never, that prison right there, that seven months taught me more than everything I learned on the street, everything I’ve learned out there, and most of all it taught me to be a good person. That’s why I’m so good to all my subs in El Paso, I treat em all with the utmost respect, and them guys all know it too. I’m a different kinda cat baby, I’m a different kinda cat.”

By this time I was thoroughly enthralled by Winn the Cowboy. 

“Well you’ve got the right guy in the truck, if you wanna hear some cowboy stories I’ve damn sure got some.”

“I would love some cowboy stories,” I said, barely containing my excitement at my good luck. He laughed like a guy holding aces. “You mentioned like that before your son was a big rodeo star that you, you were top ten in the world at some point?”

“I was, you know I was ropin steers, and, called steer trippin, you know what steer trippin is at all?”

“No what’s that?”

“Well steer trippin is when you run in you rope the horns you throw a loop around the back and then you ride off and you whirl that steer n trip eem, n you get offa horseback n you ride away, n then you go n gather three legs on a cow that weighs seven or eight hunnerd. And that’s what I was doin, and man I’ve been to rodeos all over the world and I’ve just, but, you know, right now the most important thing to me isss,” and then he paused and went kt kt out the side of his mouth, those two clicks like he was calling a cat or about to deliver a catchphrase, “is just bein a good person. I don’t need all that faame and fortune, and, you know all them gold buckles— You oughtta see my son’s house, he just won, last weekend he won, won the Turquoise Circuit…” Winn went on a long time about all his son’s achievements: he was top 3 in the world, his face was right on the ticket for the World Finals. He also showed me his daughter; he couldn’t have been more proud of the both of them. He talked about how his millionaire son always tried to get him a new truck, but he didn’t want it; he liked his old beat up dirty truck with the broken fender just fine. “I said son… this is meee! I like it!”

“It’s a nice truck, nuttin wrong with it.” He coughed here, but he was a pro-vax cowboy and I wasn’t too worried.

“It’s got 240,000 miles on, I don’t owe a dime on it, it runs like a champ…” he said, before knocking on a square of wood screwed into the center console between us. “Knock on some wood, cowboy.” That line really knocked me out. This was the second time he said “Knock on wood, cowboy,” while knocking on wood; he would do it one more time later on, after I’d stopped recording, and I asked him then if he had installed the wood panel on his console specifically for that purpose. He had.

“See these short britches right here? Had hip operated on, right after I got out of prison, I got my hip operated on. Well I tried puttin some regular pants back on and I had this big scar on my side and stitches and it kept rubbin it sore, so I put on some short britches. That was four years ago. I’ve not had a pair of long pants— that’s why my legs are so tan— I have not had a pair of britches on. In. Four. Years. Not four years. Every night— if I go out to dinner with my girl, with one of my girls, I’ll put on a nice shirt, nice pair of this, same… my better shoes, different cowboy hat…” I laughed. You can imagine I’m giving lots of short affirmations and reactions during all of these monologues, when you would think it appropriate. “It’s what it is, what it is man,” he said laughing with me. “And people see me and they say, ‘Are you really a cowboy?’ I got a rope in the back of my fuckin truck right there! You can’t see… I carry two ropes in my truck. I’m gon tell you another story in a minute. You prolly think, oh fuck, I got in with a craaazy motherfucker, but…”

“Nah this is great”

“… And so north of El Paso they’ve got the White Sands Missile Range, and they have, they have some animals turned loose out there from Africa called orex, dyou know what an orex is?”

“No, no…”

“I’ll show you”

“I been to White Sands though, White Sands is real pretty,”

“Yeah but I’m just, they, they got wild animals from Africa they turned loose there cause its its the perfect habitat to raise these animals. Well one of em, kinda, there’s no border fences there, and one of em wandered down in to El Paso, last October. I’m drivin down Montana, busy road, six oclock seven oclock at night, shopping center here, and I look over, and there’s about 80 people all the way around this thing, there’s a orex in the middle, there’s the state cops, there’s uh border patrol there’s game and fish there’s city workers, and they’re all out there, they been chasin this fuckin orex for two fuckin hours, two fuckin hours, they don’t, I, I just pull up I’m like what’s goin on here, I pull up, I pull up in this white fuckin truck of course, the good guy, I git out I git my rope I walk over there n I said ‘officer’ I said ‘you guys havin trouble?’ ‘Well we can’t catch this we don’t know…’ I said ‘I’ll tell y’all what y’all gon do.’ I said ‘You cops keep that orex from goin in that road over there, you guys give me, you give me ten minutes, and I’ll have that motherfucker roped, I’ll have eem on the ground, I’ll have eem tied, and you game wardens can load eem and get eem out of here.’ And this fuckin sergeant just comes up to me all gruff says to me ‘You gotta understand that is a wild animal, he could hurt someone.’ I said ‘The best thing for you to do, is just to back the fuck up dude. Just back the fuck up and get outta my way.’ Well I move eem around, and I’m tryin get eem right and get eem and I told them cops ‘Put your lights right in his eyes’ so we can kinda blind eem, so I can sneak up and rope him. Well I’m right next to a fuckin Burger King. I reach up there and I snag this sunofabitch when I mean snag him I mean I roped him, so he runs up the side of my truck right here, cause I, and this lady, a lady was in the drive-thru ordering lunch, dinner, and I roped that sumbitch and he slide the rope through my hands and he comes right here and I hit eem, and that sumbitch bailed up as high as he could and landed on the front of her car! This lady jumped out that door right there and RAN across that parking lot,” I’m laughing my ass off at this point, I’ve been laughing at every point you might think to laugh when you’re really listening to someone tell a story, “she ran across the parking lot saying, ‘He’s got a wild animal! HE’S GOT A WILD ANIMAL!’ Ahahahaaaa! And so after that, I told them cops ‘Cmere, hurry hurry hurry hurry!’, they choked him down, I went over and bulldogged him down, and tied three legs, put a tarp over his eyes, and they hauled him outta there.”

“Wow.”

“I made the news, it made the news and everything.”

“That’s sick, that’s awesome!”

“And it was right, and it was right before Christmas, and it says, it says ‘Local Cowboy Saves the Reindeer.’” I laughed again. “That’s what, I’ma show you, I don’t, I don’t want you to think I’m just bullshittin you—”

“No, no no, I I I believe you, I—”

“I couldn’t make a story up that good could I?”

“No no it’s a pretty good story yeah I… it, it stretches the powers of fiction.”

At this point in the recording there is silence, and then I laugh again at what I had just said for my future self. Winn did not know I was recording, but he was delighted at the prospect of being in my novel. Every direct quote I have used so far is from the first 11 minutes of my hourlong recording; we spent over five hours together. The density of muchness in a given conversation with a stranger is engrossing when you’re in it, and mind-boggling from the outside. 

There’s so much else to say about Winn that wasn’t recorded, so many precious details I’m lucky enough to remember. He grew up poor, and at 16 he left his alcoholic dad to go live in a boxcar on a farm near Amarillo, where he stayed for two years keeping the horses shod without ever once actually going into Amarillo. His grandma was full Cherokee, which explained a bit of his leatheriness. He has seen many beautiful places that I have seen and many that I have not. Passing through Lordsburg he said it was the ugliest town in the world, but that you could live there on Social Security and just sort of exist. He bought me a Big Mac there, and told me about all the most beautiful places in New Mexico. We crossed over the Continental Divide, and it looked flat. He pointed out to me pecan trees and pistachio trees, and let me know when we were in chili country. He loves this stretch of land. His current girlfriend’s son recently died drunk driving, and she felt guilty because she’d let him. He used to have girlfriends all over Las Cruces, and back in the day before cell phones you could have a couple girlfriends and they’d never find out about one another. He kept on calling me cowboy and pardner, and occasionally asked me to make sure we didn’t crash while he tried to show me pictures on his phone.

Eventually we got to El Paso, his home. He pointed out different parts of the massive city to me, including houses he built, and the tiny piece of New Mexico that’s surrounded by Texas. He took us on a faster highway the locals know about, which goes right along the border wall that President Trump built. Winn hates the wall. He thinks it’s the stupidest waste of money he’s ever seen, and told me about how much steel is rusting since the whole useless project is staying unfinished. He loves the Mexican people he works with. We drove along the highway looking down into Juarez, the larger Mexican city abutting El Paso, and Winn told me all about their infrastructure while I admired their colorful houses. Winn pointed out various border patrol checkpoints, and mountains where border patrol captured 300 people a month trying to cross. Winn said he respects the Mexican migrants for wanting to make a better life for themselves; he says that’s the American dream. I told Winn that he broke every one of my stereotypes about cowboys.

Winn dropped Waldo and I off around 4:30 pm at a major truck stop center, a Petro off I-10 east of the city. It was the exact same truck stop I got stuck at while hitching when I was 18, the truck stop where I met the kind Cajun who gave me his mom’s number so I could stay with her in Louisiana. Winn gave me $20 and his phone number; he made me promise to call him on Thanksgiving when I was home safe with my family in Massachusetts. I promised, and I kept the promise. I walked over to the same I-10 East on-ramp where I’d been picked up by Robert in 2017, and I put my thumb out to fish for big rigs going all the way across Texas. You wouldn’t believe how fast I got a ride.