The Joys of Gambling

By Johnny Hughes © 2009

Saratoga, New York, 1925. A fictional memoir.

"The hardest thing in the world is to find an honest partner in a skin game." - Arnold Rothstein.

Sean O'Malley pulled his new $3150 Pierce Arrow Coach up in front of the American Hotel. He limped slowly into the busy lobby, leaning on his cane, and stopping to rest every few paces. His left arm, and leg weren't aligned right, as if he had been a stroke victim. His neck was twisted to the left, and his face seemed pinched in agonizing, and heroic pain. Sean could only make it as far as a couch near the front desk. On the other end of that couch sat Clarice Biddle, the single most prolific gossip on the East Coast. Sean summoned the desk clerk, with a slow, tortured motion.

"I'm Sean O'Malley. I have a suite reserved and paid for. Will you check to see if a parcel has arrived for me? It is my family medicine. It is urgent."

His voice was strained, and he seemed not able to raise his head.

"I'll go check. So, you are Sean O'Malley, the man who will play any card game. I've heard the gamblers talking about you."

The desk clerk was loud and enthusiastic. Saratoga Springs, New York in August was the gambling capital of America in the 1920s, with the horses, the spa waters, large and ornate casinos, and America's wealthiest citizens in a gilded age, when money and wine were treated like water.

"I need to rest here. Go see first about the family tonic. Has it arrived? I can't play any one until I get my health back."

Sean O'Malley had bribed this desk clerk, though his cousin Patrick who was persona non grata in New York, due to his successful stock scams. They were part of five generations of the Traveling O'Malleys: gamblers, con men, musicians, medicine show owners, carnival barkers. For generations, O'Malleys were around hotels, conventions, county fairs, golf courses, country clubs, and race tracks, selling little bottles of O'Malley's Family Tonic: Secret Irish Herbs.

After explaining to Mrs. Biddle that the tonic was not for sale, Sean spoke knowingly of holly, fennel, oak, hemp, and secret herbs that bonded the rest. His dear grandmother, Grace, grew the herbs in Duke, Oklahoma, but they had been grown in his family in Ireland and America for eight hundred years. Telling the hard of hearing Mrs. Biddle something was much like radio advertising. She would repeat it all through the day.

"Now, I know and can prove the family tonic helps to heal, by changing the blood. But in Ireland, there were secret herbs that led to good fortune and luck. I can't prove that, but I believe it, and that is why I am a gambler. I am living proof it works."

That afternoon, Sean limped up to a croquet game on the lawn. Nearby, some men were pitching washers, and were quite animated and verbal in their obvious gambling pleasure. One of the men asked Sean if he would like to join in, and he declined due to his health. Now Abner Cosden asked directly, "So, you are Sean O'Malley, the man who will play any card game?"

Now Sean told them he was a traveling gambler that would bet on almost anything, if his health came back.

Harold "Mike" Vanderbilt, from one of America's richest families, asked, "Do you play bridge? We were looking for a fourth."

"I'd play for mild stakes. At the Biltmore in Atlanta, I ran into three of them playing in together. My partner would bid high, get doubled, and go down as much as possible. The card room manager said I did not have to pay. I like one on one games, any form of poker, rummy. I'd throw those washers, if I was well. These other fellows look like they are on the square, but I'm not so sure about you."

The desk clerk came running across the lawn with the earth-shaking news. The tonic had arrived. He took Sean's arm and helped him back to the hotel. A pitiful sight. He stopped twice to rest on his cane.

The next morning, Sean O'Malley, athletic, and amazingly cheerful bounded down the stairs and into the lobby, the very picture of robust health at thirty-three. His thick, curly, auburn hair had been pressed flat the day before. He jumped into the air and clicked his heels. He sat with Mrs. Biddle, and repeated often his thanks for her kindness, before the tonic worked its expected, and proven rejuvenating magic. This was a Friday. Sean confided to her that he was a betting agent for New York's biggest gambler, Arnold Rothstein. He would be betting only the fourth and fifth races the next day, and then leaving town. He sold her two, quarter-pint bottles of the tonic at $100 a bottle, but told her he only had a wee, tiny supply.

That afternoon, Sean purposelessly ran into Vanderbilt, Cosden, and their group at the race track club house.

"I've got me health back, and I can beat any of you guys at anything," Sean said, almost up in Vanderbilt's face.

Vanderbilt was six years older, forty pounds heavier, and three inches taller than Sean, who was cocky, at best. Again, Harold Vanderbilt started a discussion of bridge, and then gin rummy. The brash newcomer was invited to their box. Cosden asked if he was really Rothstein's betting agent, and in the same breath, what horse might A.R. favor.

Sean O'Malley didn't seem to even notice the first two races, telling bawdy jokes, and recounting his big poker wins, and then losses, in the Dallas Petroleum Club. He sang parts of "Danny Boy" in a fine Irish tenor, and danced a jig. He spoke to Harold Vanderbilt as if they were equals, and he was a bit insulting to a man that was used to everyone catering to his every whim, and agreeing with his every opinion. In the first hour they met, Sean told him he was wrong often, and he liked it. Sean read Harold Vanderbilt's steel-blue eyes intently. He knew the man had a great sense of, and enjoyment of humor. They hit is off instantly.

Now after swearing them to secrecy, which Traveling O'Malleys did several times in any given day any place wealthy folks gathered, Sean said honor forbade him telling them Rothstein's selection of a horse, but he'd share the mechanics.

"I'll meet this big fat man in a white coat right out there, about five minutes before the bell. I'll hand him a signed bet chit, and he'll sign a chit for me."

The traditional bell at Saratoga rang seventeen minutes before post time.

Before the fourth race, Sean O'Malley ran back to the box, frantic, visibly upset.

"He didn't show up. Something went wrong. I don't have much money on me."

And after clever conversation full of O'Malley stock phrases: promise, guarantee, cross my heart, opportunity, chance of a lifetime, swear on the Bible, trust me, I'm feeling lucky, and decide now. Abner Cosden and Richard Barton rushed off to the bookmakers and wagered $10,000 each on Gaelic Mist to place. The filly was rated second in the betting odds at three to one. They had agreed to pay Sean, "a wee finder's fee, the customary steerer's fee in any gambling joint, saw-dust or rug, twenty per cent."

Harold Vanderbilt had remained silent, with his arms crossed, grinning. An O'Malley can smell skepticism, their century-old enemy.

"You can sell them some snake oil when they get back," he said. "I liked the way you did that. You have that Irish gift of gab."

Vanderbilt didn't wager on the race.

"You should have bet something. You might be walking around real lucky and not know of it," Sean said.

Sean said he was going to make a bet and walked down into the crowd. He could hear the announcer with no good news about Gaelic Mist. He was contemplating an O'Malley standard: Take a gypsy's leave. He walked toward the exit, and then the announcer said the scarlet and black silks were moving up fast on the outside. As Gaelic Mist was headed for the winner's circle, Sean was back in the Vanderbilt box.

"Did you cheer? Oh, did you cheer? We will not forget this day. Did you see her come from behind?"

After back slaps all around and some conversation, he noticed Vanderbilt whispering to the others, and they paid him over six thousand in cash for a few minutes work, with no risk of his own funds. Typical O'Malley proposition.

On the fifth race, Sean went through the same elaborate routine, repeating each O'Malley stock phrase like an ancient litany. He finally confided that Dublin Morning was Rothstein's choice on a place bet. Again, Barton and Cosden went to bet, this time even more eagerly. Vanderbilt did not, but enjoyed the whole mini-drama immensely, calling Sean correctly, "a world-class tout, but a tout none the less."

Sean told him that he really believed that the secret herbs in the tonic brought good health, and that he could prove it.

"And there are herbs some Irish long ago knew brought good fortune. Good luck. Now, I can prove the tonic restores health, but I also believe it brings good luck. A gambler has to believe in luck to enjoy his life. You can book me on this filly."

He wanted to get Harold Vanderbilt gambling with him personally.

Sean O'Malley ended up betting Harold Vanderbilt three thousand dollars on Dublin Morning to place, the way he always bet horses to run second or first, at track odds. Again, it was an Irish-named filly that showed all the other horses their backside. Cosden and Barton were eager to pay Sean his "finder's fee." And now Sean O'Malley and Harold Vanderbilt bet $1000 on each of the next three races, and Harold wrote down the bets. Then Sean left, saying he had run out of the tonic, trusting his new friend to tell him the outcome of their wager back at the hotel. Harold won all three. Sean's trap was set and baited. Not all trappers wear fur caps.

Right before sundown, a messenger woke Sean from his nap with a knock on the door of his suite at the American. Mr. Vanderbilt wanted to play some cards, and collect some money he was owed on the horses.

Sean took all the money he had in the world, thirty-two thousand dollars.
Sean didn't know they made hotel suites the size of Vanderbilt's. They played cards with blue and red Bicycles, and decks with Rembrandts and Titians. There was a card table, with padded, leather chairs. They played high draw poker at first, using no chips, just money. Vanderbilt sent this silent, pained, hulk of a man servant/bodyguard for plenty of ten and twenty dollar bills. He stayed out in the hall. Sean knew an O'Malley principle: With a rich man, don't let him get off winner. Keep him behind. He cares about the win or the loss, not the money. They played stud.

When Vanderbilt suggested deuces wild, Sean said, "I'll play a children's game, but I'd rather try gin rummy. You aren't any good at any thing we have tried yet. So far, it doesn't look like you could beat Rin Tin Tin."

Sean took off the coat of his tan, silk suit, and put it on the back of his chair. Harold walked the length of the room, and hung his coat in a closet, turning his back on Sean, who could have peaked at his hand.

When Sean would shuffle, he would do so very, very slowly, with lots of slow cuts to make it apparent his hands were easy to see. He was not cheating, in case they had heard of his cousins. Sean never cheated, but he sure knew how.

Soon, Sean was calling his new friend Mike at his suggestion, and telling colorful stories of his family, admitting they did the shell game, and sold gold mine stock, but he swore the tonic was not part of any con. He would get passionate about only the tonic. He told of an uncle who went nearly crazy finally believing he actually could make it rain, driving and driving, and always hitting rain sooner or later. He told of the time he had hopped freight trains from Dallas to Kansas City in a race for a $300 bet, and lost. He said he'd never cheat, citing the time his own father was thrown from a moving train nine miles from Albuquerque for suspected cheating at high draw. Mike was laughing so hard he stopped the game when Sean told of being a failure in his three week career as an Irish tenor in vaudeville.

When Mike dealt, he'd put Sean's hand on the bottom, flash cards, and shuffle poorly, against a man with this skilled, practiced, most amazing ability to memorize the card locations from another man's shuffling. When he was two games of gin rummy ahead, Sean knew he could beat Mike like a broke drum, anytime he wanted. They both sipped Irish whiskey over ice slowly. Mike played his hand. Sean played both, knowing what cards Mike needed, and playing defense masterfully.

As the hours rolled by, they discussed Sherwood Anderson, John Dos Pasos, and Ernest Hemingway. They agreed Arnold Rothstein was the model for F. Scott Fitzgerald's The Great Gatsby. Mike kept score of all the bets in a neat, tiny lawyer's script with his Eversharp pen. The same hand ran several railroads. Once when he blitzed Sean, with Sean's help, Mike called out, "Irish need not apply!"

The next time Sean won a hand he called Mike, "Yacht boy." Now Mike was angry for real, and Sean picked up on it. It was in the newspapers telling of all the major yacht races Vanderbilt had won.

When they talked of all the things they could bet on, they agreed to throw washers, shoot pool, and putt on a golf course, but not play the course. Sean traveled with horse shoes, washers, a pool cue, a bowling ball, and a golf putter. He was too busy around the club house to go for the full course. He had mastered prop bets, usually surrounding making a putt twice or three times. Mike would talk about bridge and bidding systems for bridge which bored Sean. They ordered Porter House steaks with all the trimmings, wine, Irish whiskey, beer, oysters, chocolate ice cream, and pheasant as an after thought.

They took a break while waiting for room service. Mike turned up the radio just as Al Jolson started singing, "I'm Sitting On Top of the World." Sean was on his feet, dancing the Jolson steps, and pantomiming the first verse. Then he started singing in his fine, schooled, Irish tenor, as loud as the radio. Mike was slapping his hand on the table, and then mid-song, he joined the singing, timidly at first and then louder with a rich, surprising baritone. After the song,Sean offered to bet $500 he knew all the words to "Danny Boy."

Mike said, "There's a Mick in Herald Square will sing it all day long for a dime a time. No bet. No tonic. No Irish need apply."

After dinner, they threw quarters at the wall for $500 a throw. The one with the closest quarter won. Sean kicked off his two-toned Florshiems. Mike, clearly drunk, removed his own hand-made shoes, and threw his tie on the floor. This took on some great meaning for the drunken aristocrat. Sean could win at will. They threw cards into the hat, and Sean offered two to one odds, after the third round. Mike insisted that they use a Homberg he had in the closet, and not Sean's fedora, which was obviously "a trick hat." When they were not doing anything else, O'Malleys practiced throwing things. Sean pretended not to be keeping exact track of all the bets, with Mike carefully writing every thing down. He knew he was up over $20,000 to a man that loved it. An O'Malley principle: If they are laughing and losing, they stole that money.

When Cosden and Abbot came by the suite in tuxedos, they were headed for the Brook, Rothstein's fancy casino and a midnight meal.

Sean yelled, "Let them in, they might not win."

Mike told them to come back later for bridge or poker. Sean thought he had died and gone to O'Malley gambling heaven.

Mike would mention knowing Jack Dempsey, the Astors, President Coolidge, Eddie Cantor, and Fanny Brice or having his own private railroad car in town, and the number of railroads the Vanderbilts controlled in a matter of fact, non-bragging way. Sean acted like he was talking about the weather.

"One time my family had more ships than yours. Grace O'Malley, the pirate Queen's own family had a fleet that traded all over the world, around 1500. She was bright red-headed, and is well known in Irish history. She had lands, fleets of ships, castles and lost them to the English, all but one wee ship. She sailed to England itself, and talked to Queen Elizabeth, the first one. They freed her brother and son who they held captive, but they never returned her estate, as promised. The English was grabbing off Ireland little bits at a time. There is always a Grace in our family. My grandmother grows, and mixes the herbs. Conditions on the ships coming over from Ireland were terrible. Many were sick. Many died. Not one O'Malley even got sick."

"Why don't you sell that stuff mail order? Everyone is into health. Half the Whitneys eat Fleischmman's Yeast each day. It tastes horrible. They advertise Grape Nuts as a cure all in the Saturday Evening Post," Mike said.

The first time Mike invited Sean to visit, and stay at his legendary estate, Idle Hours on Long Island, Sean said no, he'd just won the Pierce Arrow in Dallas, and heard of a huge open poker game at the Palmer House in Chicago. Later, he showed more interest, realizing Mike was obsessed with a bridge.

When Mike said, "The unions and the coal strikes hurt the working man. They hurt our railroads. They never help anyone..."

Sean interrupted.

"Now you've discovered a subject on which we will always disagree, and for the sake of our new, dear friendship, we should not discuss unions, because I am firmly for the West Virginia coal miners, and the unions, and wonder why one man needs the whole top floor of a hotel."

His voice was rising. The alcohol fueled a real anger.

"There are three suites up here," Mike said.

It was after four a.m. and the alcohol had loosened tongues. They stopped to throw quarters at the wall again to wake up, and stretch their legs. Sean offered a proposition bet, saying he could throw forty playing cards in the hat, out of a fifty -two card deck. Drunk as he was, he was finally gambling, since he was not sure he could do it. He measured out sixteen paces from a large, leather chair and placed the Homberg there. They agreed on three thousand as the wager. While Sean was in the bathroom, Mike moved the hat out another nine paces. Sean missed the first two throws, then realized what had happened. He let up a sequel. Mike was triumphant, gloating, laughing. An O'Malley principle: We are entertainers. Let the marks have a big time.

Finally, with the hat back in place, Sean won the bet with the O'Malley signature one card to spare.

The two men played until six a.m., and Sean won $32,000. The next morning, Sean sold seventeen bottles of the tonic in the lobby, thanks to Mrs. Biddle, and the desk clerk. He stayed three more days, and never won another horse race bet with his bet them to place system.

A month later, Sean O'Malley arrived for a two day visit at Idle Hours, the Vanderbilt estate on Long Island. He stayed nine days: playing bridge, gin, poker, pool, throwing things, and fishing, swimming, and yachting, but only once. Harold Vanderbilt invented contract bridge, developing many of his ideas playing with Sean O'Malley. They played in bridge tournaments as partners for several years. Sean had a lifetime pass on several railroads. One day he ran into Vanderbilt on a Manhattan sidewalk. Vanderbilt took him to his tailor for a fitting, and ordered fourteen suits for Sean, in a array of fabrics, and conservative designs. Both won national bridge tournaments, but never together, as partners. They were known for yelling at each other, but also for betting on every thing they could think of. Mike would call with bets on Ivey league football, major league baseball, horses, boxing matches, elections. Sean always knew Mike's preference in advance, and he coppered the odds.

In 1934, a sign was posted above a massive guest bedroom at Idle Hours that read SEAN O'MALLEY'S ROOM. The two were inseparable. Sean ran large, honest poker games at Idle Hour during the worst of the depression for some of the richest Americans, many when Harold and his wife were at another estate. Sean O'Malley married Mary Kerns, a table servant he met at Idle Hour, and the Vanderbilts put them on the invitation list for all manner of parties they rarely attended.

Sean O'Malley promised Mike that he would not sell the O'Malley Family Medicine: Secret Irish Herbs at bridge tournaments or to the Vanderbilt's society friends or on any of the Vanderbilt railroads, and most especially not to the guests and staff at Idle Hour, but Sean could not stop. When Time Magazine did a cover story on bridge tournaments in 1936, it quoted Harold "Mike" Vanderbilt as saying, "my closest friend and advisor, Sean O'Malley, is the best all around card player in America."

From his side of the table, it sure looked that way. Both men lived until 1970, and remained the very best of gambling friends.


Johnny Hughes, author of the novel, Texas Poker Wisdom.