Those Grifting O'Malleys

By Johnny Hughes © 2010

"Tough times make tough people." - Benny Binion

Being an O'Malley, I was learning the grift by age fourteen and I drove a car across Texas all by myself in 1937. You go ask any old person in the Southwest if they've seen my uncle Sky O'Malley's act, and they'll remember and laugh. They had this ol' bi-plane during the Depression. They'd go to county fairs and rodeos and such. Sam Hogan, another uncle , would do some trick flying. Then when he was off on break, Sky would come out acting real drunk with a fifth of rot gut in his hand, and he'd pretend to steal the plane. Well, he'd fly all over, doing tricks, and he'd let go this here smoke trail and go flying toward the audience, and all until he crashed it right in front of a fair size crowd in Oklahoma City. He had some broke bones and what not. A Deputy Sheriff didn't know it was an act and handcuffed him.

Now Sky had done some flying bootlegging before I went on the road with him and Sam Hogan. They'd bring booze from El Paso and Mexico to Dallas, and that's how him and ol' Benny Binion got to be real close friends. They were very young bootleggers together. When Bonnie Parker and Clyde Barrow were the most famous bank robbers in America when they got gunned down by the Texas Rangers over yonder in Louisiana in 1934. They'd killed some folks, including some laws. Ol' Benny was only thirty years old, but he was already big in outlaw circles. He had big dice games in Dallas, which just kept getting bigger until he ran twenty-seven dice games in downtown Dallas during the war. He had a piece of some fancy casinos too. You know how most outlaws keep with their own kind for telling stories, and such, but ol' Benny would show out, even early on.

So, Benny comes to Sky and says he wants to hire Sky to fly a plane over Clyde Barrow's funeral to drop a floral wreath of fifty yellow roses. They went back and forth on it all one day, but Benny could talk a frog up out of a log. Clyde was real unpopular with the laws, but Sky did it anyway. It was in the Dallas newspaper, but the article didn't mention Sky or Benny.

Sky and Sam Hogan were my uncles. Sam was married into the O'Malleys with my aunt Grace. I'd been practicing cheating with cards since I was eight, but I wasn't really ready to do anything. I went on the road with them when I was fourteen. They'd leave out of Duke, Oklahoma and work every little town all the way through West Texas down to El Paso as gamblers. They both could play most anything pretty darned good. This was 1937. Sky wore these old painter's clothes, and had said he was headed for a big job, but he'd tell folks he'd lost a fortune gambling in his life. Him and Sam would shill up at dominoes, or pool, or poker if they could find it. Every town had a domino hall. They were both good players, and they'd take the O'Malley edge. They could false shuffle dominoes or playing cards, but they weren't good for any cold decks or big moves. In dominoes, Sky could hold the double six under his palm when he shuffled and throw it by Sam or himself every time, and I couldn't even see it. He'd leave some cards on the bottom of the deck and false shuffle. I could see that, which kept me half scared the whole trip.

When we first left out of Duke, Oklahoma, they both got nearly broke in a poker game in Amarillo, Texas, and nearly got in a fight. Any time trouble came up, Sky would say he was a classical pianist and couldn't hurt his hands, but Sam liked fighting, and he did the fighting for the family. Both of them were average-size guys, but wiry and strong. Sky'd give a grand speech, and there wouldn't be a fight, or I never saw one. Sky had a lock box over in El Paso, a fair spell away. Anyways, when they are acting, Sam does the winning, and Sky seems like an all-day sucker. If there was a movie house in any of those towns, we'd all three go to the movies, which wasn't smart for looking like we didn't know each other. Sky would say he looked like Errol Flynn, but he didn't.

When we got to El Paso, they were good winners and each had given me a few bucks. During the Depression, sometimes they were gambling for loose change and a few lonely singles. Sky traded for this slick shiny black Ford Roadster. He dressed up real fancy. O'Malley's have this genetic weakness for clothes that they don't need. On the way back, he'd tell how he won thousands off this banker in El Paso. Sam would tell them he was cold trailing Sky because he knew he'd blow his boodle. Well, the greed of the mark is my family's stock in trade, and it was hard to belly up to the table for all the folks hustling Sky. He'd flash a lot of cash. And Sam would win it off him, or appear to. Sometimes, Sky would figure out the best producer in a town, and end up playing him one on one something. They'd gather up all the money open, and get ready to go. Sometimes, Sky would soak a fake diamond ring to somebody right before we left.

Even with a nice, plump bankroll, Sky is always doing short cons. He'd steal milk off back porches with five hundred cash on him. We'd go in a cafe and Sky would go to praying, and Sam is calling him Reverend and all, and he'd get a free meal or something. He'd keep a dead fly in his coat pocket and slip it in the soup, and raise hell with the owner. In this pretty nice cafe, considering the depression, right outside Wichita Falls, he'd did the fly con, and the owner got madder than a hatter. He started grabbing the change out of the cash box and slamming it on the counter. Ol' Sky was scooping it up, and putting it in his handkerchief. Sky got out of there with a big ol' bunch of coins, but he could have got killed. That man was red as a fire engine.

So, they were my teachers and wouldn't much leave me be. Sky's always yakking about my education. He'd always say he was gonna buy me a new suit of clothes and a hat. Young guys like me wore a cap. In any town, I wanted to go find some folks my own age, mostly girls. We made a big circle around hitting several towns, and got to some little ol' town just north of El Paso, in New Mexico, but right by Texas. There was about thirty of them bad women, bootleggers, burglars, big 'uns, gambling at dice, poker, and pitching quarters at the line. Well, I was good at that, and Sky and Sam got to betting on me, but it wasn't much, just the experience. It was mostly a dice game, and there was no edge, except fading the square dice. They even let me fade, and I was just fourteen years old.

So, this deal came up where Sky is going to take this guy's plane and fly it to Dallas. Sky says it is a big money deal. I could tell you of several times he got flimflammed his own self. They were all drinking. Sky wants me to ride with him to make sure he stays awake. I'm not getting on any airplane with Sky O'Malley, drunk or sober, either one of us, even if I have to walk back to Oklahoma. So Sam goes, and they leave me to drive the car back. They were drinking, and they just flew off. I'd been driving lots on the highway, but I'd never driven alone. That fancy black Roadster could get you robbed or killed in those bad lands and hard times. At first it wouldn't even start, and I went to walking, madder than I have ever been before or since. Then I went back and it started easy.

I drove right to the bridge connecting El Paso and Juare. I parked the car, and walked over the bridge to Mexico. In a half a block, I bought a whiskey and coke for a nickel. It didn't take much to get me drunk, being only my fourth of fifth time. I bought this big sombrero, and two fifths of fancy, but cheap champagne. That was a mistake, because I had to carry them everywhere, and if I wore the sombrero, folks would hoorah me. It was as big as a wagon wheel. I bought this gold watch that turned my wrist green. I barely remember finding the car, and going to sleep in it. The next day, this man in a filling station is showing me how to get to Carlsbad, New Mexico and on to Lubbock. I'd never read me a road map, and the man just gave it to me. When I started to put it in the glove box, there was over five hundred dollars cash, and not a bill over a ten. I went back and gave that filling station man a ten spot, probably two weeks pay for him in those tough times. It was coming a golly whopper of a rain storm, so I figured to spend one night in a fancy hotel. O'Malleys were always hanging around the lobby of a swell joint looking for some action. I stayed downtown at the Plaza Hotel four days. Each morning and evening I'd know I should call the farm in Duke, but somehow I never did. In order to avoid the law, and look like a fellow who was not driving a bent car, I bought a new suit of clothes, and my first fedora. Everyone knows the laws will leave a rich man or his son alone. I even got a tall-collar, stiff, white shirt, but I only wore it once. I'd eat at the hotel in a fancy dining room with a table cloth and all. They had a lamb and potato dish I still remember.

Well, they joke about that trip when they swap O'Malley family stories. I tried to marry a gal in Big Spring, and her daddy came at me with a deer hunting rifle. I lost $100 in a poker game at the domino hall there, and I tried to claim me being only fourteen, it wasn't fair. I looked all grown up, and I nearly got whupped over it. I stayed at a motor court in Lubbock about a week, and ate at a cafe every single night. I'd go downtown to the picture show every afternoon, and buy something, a shirt or shoes or something. And I took to wearing a suit, tie, and a hat. I bought another black fedora with red, green, and brown feathers. It had a white silk lining. They say the people in Lubbock, Texas are the friendliest in the world, and I found no reason to question that.

Never said it, but I'm Pat O'Malley, not the famous wrestler. He was my cousin. The main thing about that trip was that I was alone for the very first time, and I had lots of time to think or daydream. I got to liking just driving down the road. Being the Depression, there were lots of hitchhikers, bums by the rail yards, and general misery. So, I'd pick 'em up, sometimes three at a time. I'd buy a big ol' loaf of bread, some onions, and some bologna, and some soda water, and they'd wolf it down. Lucky, I didn't get heisted.

I'd been just stopping in towns and lallygagging around for about three weeks, when I finally decided to go on to the farm in Duke, and see what was up. I'd decided that for sure Sky wouldn't know about the money or how much anyways. I had $200 left, and the whole back seat full of new clothes, shoes, real fancy clothes. I had two fedoras and a pork-pie hat. Thinking he might not even know he'd left money there, I had made up some good stories about me winning gambling at everything all along the way. Sky was at the farm. Must have been ten of the family came out into the yard. Sky knew to the dollar how much was in that glove box. I gave him a hundred, and held out a hundred, even though he was really yelling. I knew he wouldn't hit me or anything with a yard full of laughing O'Malleys around.

They still quote what I said, "Well, just chalk up a few hundred to the price of your education."


Editor's Note: Benny Binion really did hire a plane to drop a floral wreath at Clyde Barrow's funeral in 1934, when Benny was thirty.

Johnny Hughes is the author of Texas Poker Wisdom.