The real-life gamblers and gangsters behind Damon Runyon’s Guys and Dolls

Guys and Dolls, the musical loosely based on the Broadway stories of Damon Runyon, premiered on Broadway on November 24th 1950. It ran for 1,200 performances and has been frequently revived ever since. The film version, starring Frank Sinatra as Nathan Detroit and Marlon Brando as Sky Masterson, appeared in 1955.

Even on the page, never mind in 1950s Technicolor, Runyon’s characters can sometimes seem larger than life. But many of them are, in fact, based on real people that Runyon knew on the Broadway of the 1920s and 1930s. His first biographer, writing in 1948, two years after Runyon’s death, said that any competent New York detective would recognised most of the gamblers and gunmen. But if many of them have faded from both memory and myth these days – itt’s hard to find out much about the gambler Nicely Hogan, the basis for Nicely-Nicely Johnson, for instance – it’s still possible to connect some of them to their reputed fictional counterparts.

Nathan Detroit
Nathan Detroit isn’t a big figure in Runyon’s stories, but the man on whom he is modelled was big enough for Runyon to trace not one, but two characters from him. That man was Arnold Rothstein, a still-legendary underworld figure, responsible more than anyone putting the organised into organised crime: under his guidance, the families and syndicates of criminal America were moulded into professional, quasi-corporate enterprises. “He don’t want to be known as a tough guy,” a fellow gangster said. “Rothstein wants to rob people sitting down.”

Above all, Rothstein was a financier – people called him The Big Bankroll – backing everything from Prohibition-era bootleggers and the nascent drugs trade to small-time debts and loans. The biggest bookmaker in the country, Rothstein thought he could fix anything, from the 1919 World Series baseball tournament to the city’s politicians and police. The floating crap game, Nathan Detroit’s signature enterprise, which involves moving the game’s location every night to make it hard for the police to shut down, was a Rothstein idea; every kind of floating game was. He had been running such things since 1911.

In a couple of stories, Runyon gave Rothstein the name Armand Rostenthal, and another nickname too: The Brain. Like The Brain, Rothstein conducted much of his business from a table at Lindy’s 24-hour restaurant at 1626 Broadway, between 49th and 50th Street – thinly disguised as Mindy’s by Runyon – where he reportedly drank nothing stronger than milk.

That was how Runyon knew him, because Runyon, who was a journalist by trade, spent hours there himself, listening out for stories in the chatter of the Broadway folk who drifted in and out. “I am the sedentary champion of the city,” Runyon once said. “In order to learn anything of importance, I must remain seated. Why I am the best is that I can last an entire day without causing the chair to squeak.”

Rothstein died of gunshot wounds in November 1928 after a dispute about a large gambling debt. Runyon was one of the last people to speak to him alive before he left Lindy’s that night; he made the evening the subject of one of his first stories, ‘The Brain Goes Home’.

(It’s a curious fact of literary history that Rothstein was also immortalised by Scott Fitzgerald as Meyer Wolfsheim in The Great Gatsby.)

Sky Masterson
One of Sky Masterson’s real-life counterparts is easy to spot. That’s Bat Masterson, a sometime gambler, sheriff, gunman and journalist who Runyon first encountered in his days as a junior reporter in Colorado. Masterson fought alongside Wyatt Earp in the gunfight at the OK Corral, although by the time Runyon knew him, his badge-holding, gun-blazing days were past.

But Sky has other counterparts too. One of the anecdotes told about Masterson’s gambling in the stories is of him sitting eating a bag of peanuts while watching a baseball game and betting that he could throw a peanut from second base to the homeplate on a baseball field. “Everybody knows that a peanut is too light for anybody to throw it this far,” Runyon writes. Sky wins the bet by using a peanut weighted with lead.

It’s a trick right out of the playbook of a gambler by the name of Alvin Thomas, better known as Titanic Thompson, who pulled the same scam betting he could throw a walnut over a house. Thomas was a skilled golfer and marksman, but, like Masterson, he would bet on anything – and preferred to fix the odds first.

Once, outside a town in Missouri called Joplin, Thomas dug up a new road sign, which read ‘Joplin, 20 miles’, and replanted it five miles nearer the town. The following day he made sure he drove past the sign with two gambling acquaintances. “Those boys are crazy. It’s not 20 miles to Joplin from here,” he said, conversationally. His friends both bet him $500 the sign was right. On another occasion, in a state where gambling was illegal, he was charged with ‘running a game of chance’. Thomas insisted the charges be dropped. “There wasn’t nobody in that room had a chance but me,” he told the judge.

Thompson wasn’t the only gambler in that era who would make extravagant bets, of course. Jo Swerling and Abe Burrows, who wrote the script for Guys and Dolls, make Nathan Detroit say he once saw Sky bet on which raindrop on a window pane would reach the bottom first. That bet was actually made in New York’s Waldorf-Astoria by a long-forgotten industrialist named John Warne Gates, popularly known as Bet-A-Million Gates for just such reasons.

Miss Missouri Martin
Some of the most common recurring locations in the stories, besides Mindy’s, are the nightclubs run by Miss Missouri Martin – ‘Mizzoo’ for short – who “tells everything she knows as soon as she knows it, which is very often before it happens”.

This is in reality actress, entrepreneur and star of the New York nightclub scene Texas Guinan. Guinan ran various clubs during the 1920s, including the El Fey Club at 123 West 45th Street – alongside gangster Larry Fey, bankrolled here by Rothstein; the Texas Guinan Club at 117 West 48th Street; and the 300 Club at 151 West 54th Street. This last one turns up unfictionalised in Runyon’s Bloodhounds of Broadway story, featuring “many beautiful young dolls who dance around with no more clothes on them than will make a pad for a crutch”.

Guinan’s clubs typically didn’t really get going until after 3am – the time at which clubs were meant to close. She was arrested on numerous occasions – so often, in fact, that her band were instructed to break into ‘The Prisoners Song’ every time it happened. Sometimes she was charged with violating the Volstead Act – the law that introduced Prohibition to America; and sometimes, rather charmingly, with ‘maintaining a nuisance’. But she rarely spent much, if any time, behind bars. Her defence was always that she was merely an employee, and the authorities could never prove otherwise.

Guinan’s nightclubs sold fake Champagne – actually cider – at $25 a bottle. Not for nothing was “Hello, sucker!” – her catchphrase – called out at every new customer who entered her clubs.

Guinan made a number of silent films, but her biggest role, that of Texas Malone in the 1929 musical Queen of the Nightclubs, is considered a lost movie. Nevertheless, there are a few brief clips of her on Youtube, such as those here, here and here.

Unser Fritz
One of the best of Runyon’s many stories set at the racetrack is titled ‘All Horse Players Die Broke’. It’s about a once-successful gambler who has one last great streak of success – winning thousands – before losing it all on one bet. The phrase – which Runyon liked so much he also worked it into a poem – wasn’t his own, however. It was coined by a sports journalist named E Phocian Howard, who Runyon knew from around the country’s racecourses – particularly Saratoga, where they used to rent a big old house together for the August meetings.

Howard, known to his friends as Phoce, was an eccentric figure, even by the standards of Runyon’s circle. He travelled everywhere in a chauffeur-driven Rolls-Royce which dated back to the first years of the century, and his wardrobe – which reportedly never included less than a hundred suits – was often of a similar vintage. His chauffeur, a man named Ben Jones – more of a factotum, really – kept fried chicken on the front seat ready to feed any friends of Phoce’s who didn’t have money left for food at the end of the day’s races. Sometimes, when Phoce didn’t have the money for Jones’ salary, he would swap places with him and drive the car himself while Jones relaxed in the back.

If Phoce wasn’t gambling unsuccessfully at the track he liked to gamble unsuccessfully at faro, a then-popular card game, also known as ‘bucking the tiger’ for the image on the back of the cards. When he did win, he was notorious for being a soft touch for sob stories.

He died, aged 55, with just $2.37 left in his pocket. The day before he had won thousands at the races, but before he had even reached his car, he had given most of it to hustlers with hard-luck stories. The rest he lost that evening at cards.

Runyon suggested ‘All Horse Players Die Broke’ should be inscribed on Howard’s tombstone. Phoce’s family did not agree.

The Lemon-Drop Kid
The plot of Guys and Dolls combines two Runyon tales: ‘The Idyll of Miss Sarah Brown’ and ‘Blood Pressure’. But over twenty movies have been made from his stories, with 1951’s The Lemon-Drop Kid, starring Bob Hope in the title role, being one of the best remembered. Based on the story of the same name, it’s about “a guy whose business is telling the tale”. A con artist, that is. “Nobody,” Runyon writes, “can tell the tale any better than the Lemon-Drop Kid.”

The man Runyon had in mind was certainly a master of the craft. His name was Harry Morgan and he once took Al Capone for $2,000 and lived to talk about it afterwards.

The story goes that Morgan approached Capone one day with a proposition when the gangster was in a steam bath. There was a business deal, Morgan told him, a home run, that he just needed the money for momentarily. Capone would have it back with interest quick as anything. Capone gave Morgan the money. Morgan did not give it back.

Incensed, the man they called Scarface, sent some men to bring the trickster to him. They brought Morgan to Capone’s home. “Why did you pick on me?” Capone asked.

“I didn’t pick on you,” Morgan replied. “You picked on yourself.”

Capone, a man not used to being told he was a sucker, was so impressed by the man’s audacity he asked him to stay for dinner.

On another occasion, Morgan asked the actor George Raft – who himself in his early years was a driver for New York gangster Owney Madden – for the loan of pair of initialled cufflinks. A little baffled, Raft agreed. That evening, Raft was dining with a wealthy lady friend. Raft left the table briefly. Morgan slipped by and sold the cufflinks to Raft’s date as the perfect gift for her host.

A heavy smoker, Runyon died of throat cancer aged 64. In the last months of his life his larynx was so ravaged by the disease he had to write or type out his thoughts on scraps of paper.

His son, Damon Junior, said that once, during those months, he had mentioned a business acquaintance to his father. “I understand he was very close to you,” Junior said. Runyon wrote an answer and showed it to his son. “No one is close to me. Remember that,” the note said.

But that’s not quite true. One person who Runyon was close to was Otto Berman, sometimes known as Abba Dabba, immortalised in six stories by Runyon as Regret the horseplayer, one of his more warmly drawn characters, introduced as “a fat guy, and very gabby, though generally… talking about nothing but horses”.
Berman worked for the Bronx-born mobster Dutch Schulz, although in what capacity seems to be disputed.

Berman himself claimed he was a mathematical prodigy and that Schultz paid him $10,000 a week to fix his numbers racket – a kind of illegal lottery based on racetrack results which made millions for the crime syndicates that ran them. Watching the results at the track Berman said he could see the numbers arrive in waves. “They travel in packs like geese, and all you got to do is spot the lead bird,” he said.

Runyon was clearly sceptical about Berman’s gifts for prediction. He named him Regret after the horse that won the Kentucky Derby in 1915 – “the only very large bet he ever wins in his life”. And perhaps having a genius for maths really was just a story Berman told about himself. “He could do multiplication about as well as your cat,” another friend recalled.

Berman died alongside his employer in a hail of bullets at a restaurant in New Jersey in 1935. The hit had been ordered by Lucky Luciano. The papers reported that Berman was Schulz’s bodyguard. Runyon corrected them. Berman, he said, “could not be a bodyguard for a five year old”.

Dave the Dude
Another real-life Runyon character you can find on YouTube is Dave the Dude. Dave, in the stories, is by and large a big-hearted sort. Yes, he’s a bootlegger and a gunman, and yes, “guys who are not willing to do things for Dave often have bad luck”, such as being taken out for an airing; “when Dave the Dude takes a guy out for an airing the guy very often does not come back,” Runyon says. But we see Dave in Runyon’s very first story, ‘Romance in the Roaring Forties’, arranging for his girlfriend, Miss Billy Perry and a gossip columnist named Waldo Winchester (in real life Runyon’s friend Walter Winchell), who have fallen in love with each other, to get married. In ‘Madame La Gimp’, Dave likewise arranges for the old broken-down former dancer of the title to pretend to her prospective son-in-law and his family, who are Spanish nobility, that she herself is rolling in money and lives in the swankiest of New York apartments.

The real-life Dave, however, was Frank Costello, a leading member of the Luciano crime family who ran the slot-machine rackets for the mob among other things. In later life, he was sometimes referred as the ‘Prime Minister of the Underworld’. Born Francesco Castiglia in Calabria – it’s not known precisely why he changed it to Frank Costello – he was summoned to appear before the Kefauver Committee of the US Senate in 1951 investigating organised crime in America. It’s in this context that Costello can be found on YouTube here. Costello was so unhelpful he was charged with contempt and sent to prison for 18 months.

After Runyon’s death in 1946, Walter Winchell set up the Damon Runyon Memorial Cancer Fund, launched with the world’s first telethon, hosted by Milton Berle. Among the contributions was a cheque from Frank Costello for $5,000.

Johnny Brannigan
The police detective Johnny Brannigan in Guys and Dolls, who, according to the stories, “is known to carry a blackjack in his pants pocket and furthermore he is known to boff guys on their noggins with this jack if they get too fresh with him”, is very clearly the New York police officer ‘Broadway’ Johnny Broderick, who, his New York Times obituary said, “earned his fame by beating up the toughest of the hoodlums who strutted on Broadway in his gaudy era”. Gangsters, it was said, would rather go to jail than face Broderick in a fight. Jack Dempsey, the one-time heavyweight champion of the world, said that Broderick was “the only man I wouldn’t want to meet in a fight outside the ring and its rules”. President Roosevelt, visiting New York in 1936, insisted on Broderick being his personal bodyguard. After retirement Broderick sold his life story to RKO for $75,000 under the title ‘Broadway’s One-Man Riot Squad’.

Away from work, Broderick was said to be “the gentlest of men”. He wore monogrammed, cream-coloured silk underwear and enjoyed nothing more than listening to his wife play the piano at home. At such moments, a friend said, his face bore the expression “of a spanked altar boy”.

In an irony of which Runyon would surely have approved, Broderick was eventually drummed from the force for associating too freely with gangsters.

Sometimes, of course, Runyon didn’t trouble to fictionalise people: the Nick the Greek who lurks in the background of a few stories – including at Nathan Detroit’s floating crap game – is the real-life professional gambler Nick ‘the Greek’ Dandolos. Others are simply thinly disguised friends too: Good-Time Charley Bernstein, who runs several speakeasies in the stories, was Walter ‘Good Time Charley’ Friedman – the real-life nickname was Runyon’s – a boxing promoter and all-round hustler who handled the career of world heavyweight champion Primo Carnera for a while.

Still others are have more than one source: Angie the Ox, another minor character in Guys and Dolls, turns up a few times in Runyon’s stories, most notably in ‘The Old Doll’s House’, where he is introduced as “an importer [of alcohol], besides enjoying a splendid trade in other lines, including artichokes and extortion”. There actually was a gangster who cornered the New York market for artichokes so he could triple the price on them, but his name was Ciro Terranova. Angelo the Ox, meanwhile, was a man Runyon encountered in Queens, who customarily walked round with a sawn-off shot gun and a burlap bag. A favourite joke was to walk up to an unsuspecting bystander and throw the bag over their head, shouting, no doubt correctly, as he released them, “I bet you thought I was going to kill you.”

Variety reported last year that a new film version of Guys and Dolls is in the works from TriStar. Runyon’s world, and his characters, live on.

This is an extended version of a piece that first appeared on Spectator Life on November 24, 2020 to mark the 70th anniversary of the first Broadway production of Guys and Dolls.

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