ONE
A Gambler’s Son
The boy fought sleep. It was after 2 a.m., long past his bedtime, and as he sat at the kitchen table he strained to listen for the telling sounds in the chilly Pittsburgh night: the low rumbling of the Cadillac pulling into the driveway, the heavy thud of the car door shutting, the click of the front door opening.
The boy was no more than six, and he waited through the night for his father to return home from work. He was young, but he knew his father’s job was different. While other dads toiled in the smoking steel mills during the prosperous few years after the end of World War II, the boy’s father labored in a smoky mill of another kind. Where other men went to work before dawn in dungarees, the boy’s father dressed sharper than a banker and often left for work as the sun went down.
The two-story house on the South Side at 2017 Sarah Street was silent. The boy was nodding off. But when the front door opened, the kid sprung into action. He popped the question before his father had time to remove his hat and overcoat.
“Can we throw ‘em, dad?” he asked. “Can we throw the dice?”
“Of course we can,” the father said, smiling.
With that, the kitchen-table crap game was open for business.
Where other fathers and sons might toss a baseball, Chester Stupak and his boy, Bobby, pitched dice. It was the boy’s introduction to the seductive world of random numbers. Years later Bob Stupak would recall that, while other children were concentrating on addition and subtraction, he had long since graduated to multiplication, division, and something rarely taught in any elementary school, the 36 combinations possible on a pair of dice. Not to mention bedtime stories that featured the Runyonesque adventures of Pittsburgh’s favorite dice dealer.
“Tell me a story, dad,” young Bobby said. “Tell me just one.”
Baby-faced Chester Stupak grinned and, as if he had memorized the stories of Runyon himself, recounted the exploits of the night’s big winner, a mouthy Malone who talked a good game but crapped out in the end and had to ask the old man for a few bucks. Which he received despite his arrogance. There was no need to humble a fellow when he was down; the best way to keep customers was to treat them with a little respect and make them think the owner was a bit of a soft touch. The tales were sanitized, to be sure, for despite what Runyon might write, the gambling racket was no place for children. But Nathan Detroit had nothing on Chester from Pittsburgh.
In Greek mythology, Palamedes invented dice and money to pass the time during the battle of Troy, and surely one of Chester’s ancestors must have been there. Chester Stupak was a proud Polish American who possessed a legendary gift for dice and the numbers lottery that became Pittsburgh institutions. If he had a mythical connection to the dice, he also possessed a keen understanding of customer relations. He refined the art on his way to winning friends and influencing people throughout Allegheny County from the end of the war well into the 1980s.
Pittsburgh was in the action from the start. At the confluence of the Allegheny and Monongahela rivers, where the Ohio River is formed, the Indians founded the village of Shannopin in the late 17th century. It became a crossroads for fur traders and adventurers and emerged as an incorporated city in 1816.
With large mineral deposits, abundant coal fields in western Pennsylvania and West Virginia, and river access, Pittsburgh was ideally located in the heart of America’s industrial coming of age. The city was shrouded in the smoky cloak of progress, and its steel mills provided economic hope and back-breaking work for generations of immigrant laborers.
The son of immigrant Poles, Chester Stupak was born June 7, 1914, on Pittsburgh’s South Side. The muscular, seething city on the South Side of the Monongahela defined his world, as it did thousands of immigrants from Eastern Europe, many of whom lived within walking distance of the domed St. John the Baptist Ukrainian Catholic Church on South 7th Street. Ordinary row houses lined the neighborhood; up on 27th Street the mills belched black smoke and swallowed up laborers each morning.
Young Chester might have joined those mill workers had he not had the odd fortune of losing his life savings as a teenager to a sharp-shooting dice dealer with a back-alley crap game. In that early humiliation, he discovered something irresistible in the dice and came away with the knowledge that a gambler’s reputation might be soiled in a blue-collar town, but his hands stayed clean.
If one man could take all his money with such ease, then couldn’t anyone provide the dice and rope the players?
Chester walked to a dime store, purchased a pair of dice, and went into business for himself. He remained in Pittsburgh’s gambling rackets the rest of his life.
The enterprise entailed more than providing a place to play and a bankroll to cover the action. There was also the mob to consider. Only a fool took men like Frank Amato, John LaRocca, Joe Sica, and Tony Ripepi lightly. But in the World War II era, Pittsburgh was run by an even greedier gang in the form of the city’s elected leaders. Their thirst for greenbacks was unquenchable. Between the mob and the politicians, the illegal dice business was far more complicated than either eighter-from-Decatur or seven-come-eleven.
Winning money was the easy part; hanging on to it took considerable finesse.
Bob Stupak often boasts that his father, Chester Stupak, operated Pittsburgh’s longest-running crap game, from 1941 to 1991. But the man was more than a simple gambling boss with a penchant for the galloping dominos. Baby-faced Chester Stupak was a man of stature in Pittsburgh’s backroom casino circles. He was to illegal numbers and card rooms what Carnegie was to steel. Although Chester never would be able to brag that he was bigger than U.S. Steel, he could boast of being the most active, visible, and elusive operator in the city’s history. He was a man of many talents and the envy of Pittsburgh gamblers.
Chester slipped indictments the way Pittsburgh-born fighters Harry Greb and Billy Conn slipped punches. Whether he was suspected of operating a casino out of the back of a shuttered brewery or accused of offering a beat cop a couple thousand to look the other way, Chester enjoyed an uncanny run of legal luck.
It is no wonder that cops, judges, and journalists suspected that he was hedging his bets by corrupting courtroom proceedings. The final results rarely varied: Chester Stupak, his youthful face grinning from the front page of the Pittsburgh Post, managed to dodge the charges.
At various times in its history, Pittsburgh has been known as the Smoky City and “Hell With the Lid Off.” Before its urban redevelopment movement turned it into one of the nation’s sparkling cities, Pittsburgh was much maligned. When asked what needed to be done with the city, architect Frank Lloyd Wright replied, “Abandon it.” But Pittsburgh boomed during World War II. Much of the rest of the nation might have suffered from rationing, but by Armistice Day there was plenty of money floating around in America’s steel town. At times, it must have seemed as if Chester Stupak had his hands on most of it.
In Pittsburgh, his dice game was an immediate success. Not that he didn’t experience the usual irritations in the form of police raids, undercover investigators, revenue agents, and the like. But that was the cost of doing business in an illegal racket.
Unlike some of his competition, namely the strong, silent types who operated on behalf of the local mob families, Chester Stupak brought more than a pair of dice and a bankroll to the party. He brought a sense of humor and a philosophy that endeared him not only to the shortstop players who hit him up for a double sawbuck, but also to the local authorities who found him as irresistible as he was incorrigible. The fact they regularly received gifts from good old Chester kept the politicians and police officers pacified.
When it came to the game, Chester had few peers and no limit. It was one of many tales he told his son.
“But what if somebody comes in and bets too much?” a young Bob Stupak once asked his father.
“What’s the difference?” Chester said. “You cover the bet. The money eventually comes back to you.”
Chester recalled the night at his jam-packed Lotus Club when Moon Miller came bouncing through the door with his pockets stuffed with cash. The Lotus Club had operated under the nose of the police for decades, and Moon Miller knew the way to the action as well as anyone.
“Ten thousand across, Ches!” Miller called through the house.
The crowd stirred. The dice skittered across the tables. Everyone in the Lotus Club was listening.
Had Moon Miller been hitting the hard stuff?
Had he knocked over a savings and loan?
“Ten thousand across, Ches,” Miller shouted.
The guys and dolls watched through the smoke. Moon Miller was calling for a bet that, in those years shortly after the war, would have paid for three houses in the suburbs.
The pressure was on, but Chester Stupak just smiled. After some negotiations, he accepted Miller’s wager—and proceeded to lose a bundle. The players talked about it for months afterward as they traveled from all over the county to get to Chester’s big dice game.
Bobby asked, “What about all that money? Weren’t you sweating it?”
“It didn’t make no difference,” he said. “Besides, I didn’t lose. I’ve beaten Moon Miller out of that much money and more over the years. And I’ll beat him again. This was nothing but a good advertisement.”
Even though every player and police officer in Pittsburgh knew where Chester’s action took place, the law was decidedly blind to Chester’s crap game, which surely is a testament to his charisma and his cash. The unwritten rules were followed to the letter: no trouble, no violence, and nothing spilled out into the street where decent folk might be offended. And no fully marked crap tables, either. After all, the cops had a reputation to protect. In the outer county, on a farm or in a vacant house, Chester might have a roulette wheel, crap tables with a full layout, and a numbers bank that would impress a New York lottery boss. But at the Lotus Club, or wherever Chester rolled his dice inside the city limits, he kept things simple and unobtrusive. He would use a pool table, divide it with a string, and drop the dice. Players had to shoot across the string. The game was on.
Chester kept his family close to him in business. One relative was the custodian of the Lotus Club, and Chester’s wife, Florence, would always be counted on to help out with the numbers accounting. While at school, young Bobby often would go to the Lotus for lunch, carrying in a bag of burgers from the White Castle on 16th Street. As he ate, he often saw the waning moments of crap games that had been going since the previous evening.
Dice became Chester’s calling card. When he opened a supper house called Club 19 with a game in back, engraved invitations bore a pair of dice and directions to the action.
Not long after Club 19 opened in Washington County, a Pittsburgh newspaper reporter began writing scathing articles about Chester’s roulette and crap games. With a call, Chester discovered that far from being a bastion of journalistic integrity, the reporter was said to have had a piece of a mob gambling club nearby. Chester inadvertently had cut into the scribe’s action. With one eye on his rear-view mirror, Chester picked up and moved. He wasn’t afraid of a little bad publicity; he was concerned about steering clear of the knee-breakers.
“He kept waiting for the heat to go away, but it never did,” his son recalled. “The boys had the area locked up.”
Perhaps one reason for Chester Stupak’s great fortune was his ability to run honest games and to remain within handshake distance of Pittsburgh’s notorious ward bosses, who at times held a grip on the city’s vice rackets. From after-hours nightclubs to red-light brothels, the political insiders offered protection for illegal activities—for a price.
And they had competition from traditional racketeers. Mafia-type activity in the area dates as far back as the 1890s, when Sicilian-born John Bazzano Sr. assumed the role of boss of the mob family that operated in Pittsburgh and southwestern Pennsylvania. Bazzano grew fat during Prohibition, ordering the execution of rivals in the gambling and bootlegging businesses, before being ice-picked to death in 1932.
By then, the neighborhoods were riddled with hoods of every stripe.
In 1950, numbers activity in Pittsburgh topped $100 million a year, according to law-enforcement estimates. Turning to lottery sales and backroom casinos was not only a lucrative move, but it also eased pressure from the cops and district attorney. A numbers racket they could handle; blood in the street embarrassed them.
“The august, dignified, black-robed jurists for years have shown a benevolent attitude toward organized racket crime and the criminals behind it. As much as any one factor, the easy sentences imposed by both Allegheny County judges and the ‘gypsy’ jurists imported from surrounding counties, upon convicted racket criminals, are responsible for the breakdown of law enforcement against organized crime in Allegheny County,” respected investigative reporter Ray Sprigle wrote in his groundbreaking 1950 series on the city’s underground gambling empire.
“In recent years the racket has developed a new angle,” Sprigle wrote. “In some wards, by and with the consent of the ward chairman, a group of small-fry mobsters will make a deal with a topflight racket syndicate to operate as a subsidiary of the well-financed big syndicate.”
Unlike Philadelphia, where much of the gambling racket was run by the Bruno crime family, and Reading, where a Bruno faction operated multimillion-dollar backroom casinos, Pittsburgh’s mob didn’t quite measure up. Not that the city was without its home office of La Cosa Nostra. On the contrary, until 1956 Pittsburgh was known as the domain of Frank Amato, who managed to achieve a modicum of success under Pittsburgh’s close-knit system.
Then came John Sebastian LaRocca, a sort of Rodney Dangerfield of mob bosses. Try as he might to shake down local businessmen, according to Carl Sifakis’ The Mafia Encyclopedia, he was nearly laughed out of the city.
“A much-overrated mobster, John LaRocca was often described as the Mafia boss of southwestern Pennsylvania and Pittsburgh,” Sifakis wrote. “Some knowledgeable observers, however, have tended to regard him as the leader of the Mickey Mouse Mafia East, a play on the description of several west coast crime families because of their general ineffectiveness and their inability to protect their own turf from incursions by the New York and Chicago mobs.”
LaRocca simply could not compete with the “Ward Syndicates” in several of the traditional rackets, and he never gained the reputation of Bruno or western Pennsylvania crime boss Russell Buffalino.
LaRocca, however, was quite successful in extracting his percentage of the profits garnered by a group of gambling junket operators who shipped high rollers from Pittsburgh to Las Vegas. Not that millionaire status boosted his image with the New York bosses.
Legendary mob informant Vincent Teresa scoffed at LaRocca’s boss status. To Fat Vinny, LaRocca was “a mob guy from Pittsburgh who some people say is a boss but he isn’t.”
LaRocca, whose criminal career began in 1922, died in 1984. He was 82 and left a legacy as an also-ran in the underworld. The mob never could compete with Pittsburgh’s political bosses.
Perhaps he should have taken a lesson from lucky Chester Stupak.
Although the mob was capable of applying considerable pressure, there was plenty of room and plenty of action to go around. With few cops watching them and fewer politicians crowing about the evils of gambling, it was obvious to even casual observers that men like Chester Stupak had powerful friends. Chester accepted it as the cost of doing business, but in later years he stopped greasing palms.
“Whoever he had to pay, the last twenty years he stopped paying,” Bob Stupak said years later. “Whenever I would come back to Pittsburgh for a visit, I’d always ask the cab drivers if there was any action in town where a guy could shoot dice. About ninety percent of the time they would say, ‘Oh, there’s Chester’s joint on the South Side.’ The last fifty years, if anybody opened up a crap game they’d be closed in five minutes by the IRS, the CIA, whoever. But my dad operated with no trouble. He was an institution. When he died, it was over.”
It didn’t hurt to have the father of the district attorney as a dear friend. When the son got the bright idea to break up Chester’s game in the name of justice and bold newspaper headlines, the father set him straight.
“The day you raid Chester’s game is the day I don’t have a son anymore,” he said.
It helped to be able to shake hands and slap backs with the chief of police and most of his men. It also helped to have a sense of humor when the time came for the election-year roust. Chester understood that, occasionally, he would have to allow the local authorities an opportunity to do their best Claude Rains skit from Casablanca. Rains, the worldly local police chief, steps into the backroom casino at Rick’s Cafe American and exclaims that he is “shocked, shocked!” to see illegal gambling going on, even as he accepts his piece of the action. So, too, it was with Pittsburgh authorities and lucky Chester Stupak.
His first arrest came in 1946 when Allegheny County detectives noticed his involvement with a growing gambling and numbers operation. He was hauled in for operating an illegal lottery, but once reduced, the charges amounted to little more than a traffic citation. A check of police records years later revealed no disposition in the case.
By 1950, his reputation was well established. The cops occasionally took playful shots at him, but for many years he appeared unbeatable in court. After all, everybody knew about Chester and his dice game.
Regulars referred to a Stupak casino as Chester’s Place. The original Chester’s Place sat above L&M Upholstery on the second floor of a brick building located at 93 Sixteenth Street near Carson Street in the city’s 17th Ward. It was a big, airy room without plush carpet or chandeliers. The room was dominated by three pool tables marked for craps.
Although homely by Vegas standards and illegal under Pennsylvania law, Chester’s Place ran wide open day and night. If it lacked a neon sign announcing its location, perhaps it was because no gambler on the South Side needed directions to find its door. No bouncers, no B girls, no problems. Just plenty of action and a boss who seldom found reason not to smile.
Then his place became the subject of a long expose by enterprising Pittsburgh Post-Gazette writer Sprigle.
LAW DOESN’T FOOL WITH CHESTER
‘THE LAW’ DOESN’T BOTHER TO BOTHER ‘CHESTER’S PLACE,’ THAT BIG GAMBLING JOINT ON THE SOUTH SIDE, WHERE THE DICE ROLL EVERY NIGHT REGARDLESS OF WHETHER THE ‘HEAT’ IS OFF OR ON
So this is “Chester’s Place,” for years famous all over Pittsburgh. Whenever the heat goes on and the joints all over town go dark, Chester’s Place can be depended upon to keep right on clipping the boys for their paychecks.
… In every other section of Pittsburgh and Allegheny County the rackets are operated as rackets are supposed to be operated. No matter how wide-open they run, the boys at least try to give visiting newspapermen an impression of stealth and clandestinity. But not on the South Side.
There the numbers racket runs like a legal and respectable business. Nobody questions the stranger who wants to buy a slip or two, either on the races or the stocks.
Sprigle’s series of articles on Pittsburgh’s rackets led to many law-enforcement inquiries, numerous arrests, and the extreme discomfort of the city’s elected leaders.
For Chester, it was the first time he was publicly accused of being less than his own man. Nick “Yee” Terleski and James Bova, both of whom carried lengthy police records, were said to be Chester’s uninvited silent partners in the city’s most celebrated crap game. Years later, his proud son would remember things differently.
“My dad never had no partners. Some people might have thought he did, but he didn’t,” Bob Stupak said. “When the cops came in to raid the place, they’d have to arrest somebody. They’d pick a two-dollar guy, a small bettor, even though everyone knew it was Chester’s game. My old man would act like another player. The cops would ask, ‘Whose place is this?’ and a guy would stand up and say, ‘This is my place.’ The police knew, but they went along with it. The two-dollar player would take a fall, my old man would pay all the attorney’s fees, but it was always a customer who took the beef. There was no jail time involved. It’s just something the police did from time to time. The two-dollar player got instant recognition in the neighborhood and in the papers. He was a big guy for a few days.”
If he lacked partners, he did have plenty of pals. For a man in a racket as hard as Pittsburgh steel, Chester Stupak was one soft touch.
“My dad was a George. You know, a generous guy,” Bob Stupak said. “He gave away fucking money like it was water. He was the easiest fucking mark in the world. I wish I had the money he gave away. A guy would approach him and start in with a story. He didn’t want to hear the story. He’d say, ‘Here’s twenty.’ Occasionally, somebody would come up to him and try to hit him up for a hundred, which was a lot of money in those days. My dad would say, ‘I can’t loan you a hundred, but I’ll give you fifty.’
“He was always giving money to shortstops. Shortstops come in with a little bit of money. You can always count on them to be busted and looking to borrow. You can’t loan them a hundred or two hundred because they can’t afford to pay you back and they’ll stop coming into your place. So you give them half. Never loan them what they want; always give them half.”
Besides, the money had an uncanny way of returning to Chester’s tailored pockets.
Young Bobby Stupak, so awed by the wonder of the dice, was determined to make his way in the racket. Although his sisters, Nancy and Linda, would heed their father’s wishes and attend college, Bobby developed an allergic reaction to authority and conventional learning at an early age.
“I was always daydreaming and looking out the window,” he recalled years later. “I daydreamed of glory.”
And he placed bets at every opportunity. Young Bobby began playing the numbers lottery at age nine. It’s where he made his first score. He took a penny to a neighborhood grocery and handed it to the clerk. When his one-cent number turned up a winner on the thousand-number game, he won $6.
“Boy, was I taking the worst of it,” Stupak remembered. “Six hundred for one on a 999-to-1 shot.”
From that point on, he bet a little every day.
It was something else he shared with his father.
After Sprigle’s series, Chester Stupak had a difficult time keeping his name out of the newspapers. He had become a soft touch for the police. Chester was indicted on gambling and liquor charges in December 1953. When the non-jury trial finally commenced in Judge Francis J. O’Connor’s courtroom, the defense called for delay after delay. At one point, the judge permitted Chester time away from the rigors of trial to complete a Caribbean cruise. In the end, “the lucky gambler,” as the press called him, was acquitted of all charges.
Even before that case was adjudicated, Stupak was again arrested on gambling charges. His luck held, and a grand jury threw out the case.
The police kept at it. Chester, meanwhile, was franchising his action at a rapid rate. By day, he ran a pinball machine outfit on the South Side. By night, the dice rolled nonstop. By the summer of 1957, he had converted a Peters Township lumber yard into a gambling den called Club 19, and another satellite casino opened up in the basement of a private home just outside the city limits on Becks Run Road.
In December 1957, Stupak was operating out of the swanky Ozark Club in the Pittsburgh suburb of West Brownsville when his one-man parade was interrupted by a police battering ram at the door. On the way to charging Stupak with keeping a gambling house, state troopers tore apart the Ozark Club, collecting evidence and intimidating everyone but the proprietor.
Then District Attorney Michael Hanna began interrogating the troopers who pulled the raid.
“You would have thought you were on trial,” a trooper told a reporter.
Hanna was later accused of wrecking the investigators’ “perfect case” against the smiling Stupak.
William McKee, the lieutenant who led the raid, said, “It was a good case, there’s no doubt about that. We’ve done our part. The boys did a good job, no matter what anybody says.”
Whatever went on, the result was the same: a grand jury tossed out the charges against Chester—and assigned the cost of repairing his illegal gambling hall to the county.
Then came the John James bribery case, which made banner headlines in Pittsburgh’s newspapers, and surely led the police to believe that this time they had their man. In September 1958, Chester was back in court, with his partner in the numbers racket, Henry Katz, for allegedly offering hush money to James, a Pittsburgh patrolman. Far from a corrupt cop, James had been cited for bravery numerous times. He had been shot twice and stabbed once while on duty. He was a family man with a daughter at Duquesne University. James was working undercover and his effort resulted in the arrest of 17 persons connected to Pittsburgh’s underground gambling rackets. Stupak and Katz were charged with bribery, conspiracy, operating a lottery, and corrupting an officer.
The first bribe attempt came in September 1956 and the first actual cash transaction occurred months later at the Chez Dee Club in Brentwood, where Stupak slyly slipped the cop $300 under the table.
Once the news got out that he had accepted bribes from the biggest gamblers in Pittsburgh and that the state had used legal but controversial phone recordings to gather further damning evidence, James emerged as a hero to some upstanding members of the community. The wiretaps would help convict several of the accused, and James’ strong character hurt other defendants.
But Chester Stupak was no ordinary racketeer. Stupak and Katz hired bulldog defense attorney Louis Glasso and the fight was on. Glasso objected to the secretive nature of the case. He objected to the use of the wiretaps. He objected to the amount of money the cop accepted. He went so far as to say that defendant Katz, a longtime gambler who already had a federal tax-stamp conviction, had been lured into operating a numbers game by the officer.
“It’s a terrible thing to befriend a man, eat his food, drink his drinks, and then turn on him,” Glasso said.
He did not claim Stupak and Katz had not offered bribes, or that their offers were rejected. The defendants admitted as much when they took the stand in their own defense. It was, they said with a shrug, the cost of doing business.
But their attorney assured the court that the defendants had been entrapped by the deceptive cop. James promised them protection from police raids, they claimed. So they felt justified in paying him a total of $8,800.
At home, Chester’s children saved newspaper clippings and—far from being mortified—laughed at the press accounts about their father. The press became obsessed with Chester’s tailored suits, custom shoes, and youthful appearance.
“We got a kick out of the publicity,” Bob Stupak remembered years later. “When he appeared for a court date, I just remember the jacket he had on. My sisters and me, we all laughed at the stories. He was considered dapper, and he wore a Palm Beach sports jacket to court. The press commented on it. When he got home he said, ‘What the hell did I wear that goddamn jacket for?’ He took the case seriously.
“My old man, he had more shoes than I’ll ever have in my life. My dad got up in the morning, showered and shaved, and put on a suit. When he came downstairs for breakfast, he was dressed for the day in a suit and tie. I mean, he was well-dressed for breakfast! I don’t think I saw him six times in my whole life that he didn’t have a tie on. He had a wardrobe from here to China. My old man’s closet was gigantic. He had more shoes than you’d see in a shoe store, more shirts, more jackets. I don’t think I ever saw my dad casual.”
So of course the press often commented on Chester’s daily fashion statement. Although only 5-feet-7, he was a big man on the street. Imagine how the reporters crowed at his acquittal.
If the patriarch of the Stupak family was ridiculed by polite society, little Bobby never noticed. By the time he was old enough to understand what was being said about his dad, he no longer belonged to the straight world.
“When I was a kid, I thought that’s what big people did—you throw dice against the wall,” Bob Stupak recalled years later. “That’s the way I was raised forever.”
It was common for Chester and his friends to play a private game at the Sarah Street house until early in the morning. When young Bobby would come downstairs for breakfast, they would still be at it, smoking and watching the action. Florence had long ago accepted her husband’s calling. The rackets supported their family in comfort; the publicity and threat of jail were facts of the life they led.
Only a square would fail to appreciate why Chester would offer money to a cop, or why it was a business expense in Pittsburgh. After all the payoffs he had made over the years, it was argued that setting up good old Chester was downright dishonest.
The 12-member jury thought so, too.
On September 13, 1958, Stupak and Katz were found not guilty on all charges. The acquittal stood even after one juror reported to the judge that she had been offered a $300 bribe if she voted on the side of the defense.
Chester Stupak, the dapper Houdini of the Pittsburgh legal system, was free again.
Lou Adams managed Chester’s Lotus Club for six years. The Lotus was a members-only operation that featured a restaurant, bar, and dance floor. But members came for the action that went on upstairs. For obvious reasons, Chester was listed only as a member. Adams and Stupak usually were tipped to police racket-squad raids. They kept a hulking former police detective at the front door to keep out the riffraff and to spot undercover cops trying to blend into the scene.
“Everybody knew he was the owner, but he didn’t have his name on paper,” Adams said. “Chester, although a little man, had a big heart. He was a real gentleman and one of the finest guys I’ve ever met. As to fortitude, Chester didn’t let anybody screw him or fool him.”
It did not mean he ruled the Lotus with an iron fist. On the contrary.
“His theory was, ‘You can’t gamble if you don’t have a game,’ and these guys were part of the game,” Adams said. “Invariably the shortstops always came back when they had money. It was an investment.”
But there were limits to his generosity. He was no sucker.Chester was upstairs at the Lotus late one night rolling dice head-to-head with two wiseguys when Adams heard a shot ring out. Rushing upstairs, Adams passed one of the shooters desperately trying to escape. When he arrived at the scene, diminutive Chester Stupak had wrestled the second, much larger man into submission. It turned out that Chester had beaten them on the square out of several thousand dollars. They shot at him and somehow missed.
“They shot at him point-blank and hit the wall,” Adams said.
Instead of calling the police, Chester cooled down, obviously realizing that desperate men are dangerous men. Instead of throwing them out on the street, he bought them a drink. The gun-shooting crap shooters lived a long time, but they never crossed Chester Stupak again. And they continued to regularly lose their bankrolls at the Lotus Club.
The hustlers weren’t the only ones who took a shot at Chester’s cash reserves.
“A lot of police used to take advantage of Ches’s generosity,” Lou Adams said. “At Christmas, we used to give the regular beat man a ten-dollar bill and a bottle of booze. I’d buy ten or twelve cases of booze at Christmas just to give away. It was part of doing business, an expenditure for the heat, and most of the police were very cooperative. But at Christmas, we’d have cops from the North Side and the Hill District showing up at our door. They weren’t even from the South Side, but Ches made sure we took care of them anyway.”
Adams also recalled top Pittsburgh law-enforcement officials receiving up to $1,000 per month from generous Chester Stupak. The cost of doing business was expensive, indeed. Add to that the $50,000 tribute extracted from Stupak by local mob bosses, and it’s no wonder Chester was such a popular man on the South Side.
__________________
Robert Stupak was born April 6, 1942, and was hard to handle from the time he was a toddler. Florence Stupak was a strong-willed mother who managed to keep the Stupak girls in line, but had a devil of a time with young Bobby, who took to skipping class at an early age at St. Adalbert Catholic School. Adalbert of Prague’s life’s work was characterized by failure, but his impact on others was great, Alison Jones writes in Saints. Adalbert was the patron saint of Polish people, but he wasn’t having much luck with young Bob Stupak.
One morning at the home on Sarah Street, Florence Stupak let her 3-year-old son Bobby out to play in the yard while she worked in the kitchen. A few minutes later, she returned to find him missing and began to fret. Then she heard his small voice in the distance and really began to panic.
Her condition worsened when she spotted him at the top of the rickety fire escape that ran up the side of the three-story house. He was more than 30 feet above the ground, laughing as he climbed. When he reached the top, he ran around the roof, leaned over the side and giggled as his mother looked on in horror. Within minutes, family and friends gathered around the fire escape and made their plan to rescue the boy.
Young Bobby Stupak had attracted his first crowd.
By the time he was old enough to go to church, he began shirking his duties.
“He used to fall asleep in church. At St. Adalbert’s, he had to go to mass every morning,” Florence recalled. “The sister told him he wasn’t allowed to have a rosary because his mind would wander. He had to take a prayer book with him to school every morning. He was always losing his prayer book.
“One day, he just couldn’t find it. So, I had a little telephone book we kept our numbers in. It looked like a prayer book, so I gave him that to take to church.”
Little Bobby Stupak faked it flawlessly.
He was less successful at shining his mischievous light at the church. One Saturday, the day before Easter, one of the sisters emerged from the convent to find young Bobby exiting the church.
Had some miracle of faith taken place? Had the child had an epiphany? Had he made a conversion or even an attempt at penance?
No. She soon discovered that he’d lit every candle in the church. The Easter candle-lighting ceremony would be ruined unless someone acted quickly. Instead of calling the local authorities or the priest of the parish, the nun wisely dialed up Florence Stupak, who settled the debt and saved her son’s place at St. Adalbert’s.
As a scrawny seven-year-old, Bobby landed his first job as a paperboy, hawking the Pittsburgh Press and Post-Gazette on the street corner. It took weeks to convince the vendor to give the undersized kid a chance, but Bobby finally was handed five copies at four cents apiece. He would sell each paper for a nickel and pocket a penny.
His first day on the job, he felt the pain of failure. He sold four papers but couldn’t give away the fifth. Instead of admitting defeat, he stuffed the unused newspaper through a sewer grate and handed over his small change with a smile. He took no profit, but gained the confidence of the vendor.
“There was no way I was going to admit I couldn’t do the job,” he recalled decades later. “I couldn’t face defeat. I couldn’t let him know.”
His mother might have wanted him to study hard and one day merge into the straight business world, but he would have none of it. He preferred Hollywood gangsters to the squares at St. Adalbert’s. In the early years, Florence usually knew where to find her boy and often called on Lou Adams to leave the Lotus Club to comb the South Side for her wayward 11 year old.
“Bobby loved the movies,” Adams said. “When he was a kid, it wasn’t unusual for Bobby to sit through two showings. His mother used to call me at 11, 11:30 at night knowing where Bobby was. She’d ask me to go get him. There were only two theaters on the South Side. So I’d go down on Carson Street where the movies were.
“The first month he opened his club in Vegas years later, I went to see him. The first thing he said to me was, ‘Lou, did my mother send you to find me?’”
School, when he found his way to class, bored him. Longtime friends remember young Bob as a quiet classmate who was making book when other kids were reading them. He was a skinny boy equipped with plenty of tough talk, an endless supply of cigarettes, and a regular need for forged absence slips to give to school officials.
The law demanded that he attend school until he was 16, and he struggled to comply. Stupak became a regular customer for truant officers, who saw more of him than many of his teachers.
“I got nailed a few times,” he recalled years later. “Your friends would write you up a note to take in the next day.”
Three months shy of his 16th birthday, with parole clearly visible, Bob Stupak spent most of his time riding his motorcycle and working on his side jobs. He was not the kind to bag groceries at the corner store. To him, a side job meant hustling suckers, hawking discount watches from bar to bar, and watching the action on the South Side.
St. Basil’s and the 9th grade beckoned, but when the chance arose to quit school, Bob Stupak took it. He purchased an even faster Harley, much to his mother’s chagrin.
“When he’d go to school in the morning, I used to pray that telephone wouldn’t ring,” Florence said. “When he started riding motorcycles, I could barely stand it. Even today when I see anybody riding a motorcycle I bless them and make a sign of the cross. I think to myself how crazy they must be. I can’t stand motorcycles. When he would go out, I couldn’t sleep until I’d hear the door close and look at him and know he was okay.”
With his bike racing as fast as his mind, he slicked back his hair and hit the street in the heart of the James Dean era. But the Pittsburgh Kid was a rebel with an angle.
He carried with him an unofficial degree in math and accounting and the sort of bravado that comes from being a gambler’s son. He was at home on the South Side, fed off its energy, worked its lucrative netherworld. The South Side was filled with loansharks and bookmakers, con men and rough customers, and young Bob Stupak was awed by the action. He knew every cab driver and saloon bookie. He hustled a buck in pool halls and bowling alleys in Pittsburgh and Steubenville, Ohio, 39 miles away. He played the numbers every day.
Then he met Truman Beckett at Magno’s restaurant and moved up a notch on the street. In partnership with Beckett, Stupak got into the cheap-watch business, selling them at a 60 percent markup; he also became something of a small-time loanshark.
Then Bob Stupak’s life started moving even faster. He began drag racing motorcycles for trophies and glory. He crashed his motorcycle often enough to break both knees. No one questioned the skinny kid’s courage.
“Nobody else would go to that extreme,” Stupak said years later.
Meanwhile, Florence Stupak was counting her rosary beads.
“She went out and watched me race a couple times and it cooled her off a little bit,” Bob Stupak recalled. “I won when she watched, but she still didn’t like it.”
The result was more than one near-death experience, a couple of menacing tattoos on his skinny arms, and a six-foot trophy. He toured for a while on the drag racing circuit from Pennsylvania to Daytona, Florida. But glory was one thing; money was something else.
Bobby Stupak craved both in the worst way, and in the time of Elvis nothing assured more of both than the title of pop singer. His trips to the clubs of Steubenville had shown him where the action was, and he made up in confidence what he lacked in talent. If another Polish kid, Bobby Vinton, could make it big in pop music, then why couldn’t Bobby Stupak?
But first he needed to do something about the name. “Stupak” was too ethnic and didn’t exactly flow off the tongue. It was the name of a Polish kid from Pittsburgh, not a suave singing sensation or rock ’n’ roll idol.
That’s when it hit him. If he was going to be a star, why not advertise the fact?
And so Bobby Star was born.
He crooned love songs and snappy ballads and pulled off a genuine coup after a few short months. Through agent Marty Wax, he signed a recording contract with United Artists.
“I went into this big office in New York and it was just like you’d imagine,” Stupak recalled. “Mike Stewart was the president of United Artists at the time and he said, ‘Kid, I’m going to make you a big, big star.’”
Mike Stewart was a man who could get things done in New York’s payola-riddled record business. He had taken four Canadians and, largely on the strength of his image-making ability alone, turned them into wholesome international singing stars called the Four Lads. If the Four Lads could succeed with their saccharine sound, surely so could one tough Polish kid.
On his way to certain stardom, the teen idol in the making needed to work on his act and his songwriting skills. He played clubs in Pittsburgh and Steubenville with mixed results. His voice wasn’t smooth enough for love ballads, not strong enough for rock ‘n’ roll. He had the hair and the attitude, but little else.
What he needed was a gimmick. Some stars had swiveling hips. Other cool cats groomed their pompadours to perfection.
Bobby Star attracted attention with a cat of another kind—a full-grown cheetah plucked directly from the Bird and Animal Kingdom of New York. The crowds might not compare his voice to Bobby Vinton’s, but Bobby Star would be remembered around the clubs of Steubenville for his rebellious streak. When one club owner banned the animal from the stage, Bobby Star seized the moment.
With television cameras capturing the action, he coolly strutted out the door of the club and onto the sidewalk, then tied the animal to a parking meter. He dropped a dime in the slot and went back about the business of being a star.
“It was too much,” he recalled many years later. “We had the television stations and the newspapers covering it like it was a big deal. They loved it. There are a lot of things you can do with a gaff to get yourself known.
“When I stopped singing and started hollering I became good. I did a lot of hollering. It was okay. The kids liked it.”
But something happened on the way to the top. Bobby Star was not lacking in bravado, but he was a little short on talent. His first single, “Together,” fell apart immediately.
“When they released it, it was a bomb and I couldn’t get in the fucking door again,” Stupak said. “I was under contract, but I was done as far as they were concerned. Then I got pissed off. I walked away from something that guys would have cut off their left toe to have.”
In all, he recorded eight songs for United Artists, none of which made Bobby Star shine. His attempt at a sentimental Christmas standard became a ditty called “Jake the Flake.” With lyrics such as: “Here comes Jake/Jake the Flake/Jake the little white snowflake/Comin’ down from the sky/To make our Christmas all white,” it wasn’t exactly “White Christmas.”
It wasn’t long before his star began to dim. Like motorcycle racing before it, singing became a low priority. He faded from the music business and at 19 years old, weighed his options. Although it promised to give him valuable insight into the psyche of the gambler, working around his father’s crap game did not figure to put Bob Stupak on the fast track to business success. Running numbers and roping suckers for moneylenders was good for laughs and spending cash, but it wasn’t a career for a big dreamer. Drag racing on motorcycles provided the thrills, but there wasn’t much money in it and the teenager’s knees already were damaged by his red-lining style. And he really wasn’t much of a crooner. No, the young hustler definitely needed some straightening out.
Too late for the monastery, disinterested in university life, and with America’s involvement in Vietnam a few years away, he joined the National Guard and went on active duty from November 1959 to May 1960. His service status also served to cool any problems he might have had at the time with Pittsburgh law enforcement and heat from some shadowy members of the city’s illegal gambling community. At Fort Knox, Kentucky, and Fort Sill, Oklahoma, Stupak was a raw recruit, just another skinny kid growing up on the cusp of the 1960s.
He never distinguished himself in battle or saw a moment’s action, but Private Stupak still managed to stand out in the sea of drab green fatigues and butch haircuts.
He was the private with the crap game. Bob Stupak may have left his childhood behind when he joined the army, but he brought his dice with him.
Once settled in at Fort Knox, he quickly realized two things. First, though his fellow soldiers hailed from all over America, most seemed willing to gamble at a moment’s notice. Second, they barely understood how many dots there were on each die.
“Nobody knew that there were three ways to make a four on the dice, four ways to make a five, and six ways to make a seven,” Stupak said. “They had no knowledge at all of these little cubes they were gambling with.”
There was no need to shave the dice. Stupak merely adjusted the odds. The shooters figured they were getting a great deal when he offered them even money on some propositions; little did they know that the odds of making some rolls were far greater. Stupak escaped the service at the first opportunity, but he carried the lesson in human behavior with him back to Pittsburgh, then halfway around the world to Australia.
The outcome of the Stupak-Katz state trial infuriated U.S. Attorney Hubert Teitelbaum, who immediately vowed to pursue the pair. But Teitelbaum’s take was different. He claimed to have specific knowledge of high-ranking Pittsburgh officials who had been accepting bribe money from gamblers for years. He also spotted an obvious flaw in Chester Stupak’s business: the operator had neglected to purchase a $50 federal gambling tax stamp and did not appear to have been paying his annual 10-percent tribute to the U.S. government.
When it was implemented, the federal tax stamp at first confused and then confounded illegal gamblers and bookmakers. If they identified themselves as racketeers by purchasing the stamp, they set themselves up for future investigation. If they failed to pay their measly $50, they risked a certain federal violation and the dangerous intrusion of the Internal Revenue Service. Use of the tax stamp eventually was struck down in 1965 by the United States Supreme Court in the Marchetti and Grosso case. Convictions based on the law were overturned, but that came years too late for some big-city bookies and dice operators.
In 1963, the federal government was ready to try its luck against Chester Stupak.
After all he’d been through, it’s difficult to imagine such a giant being felled by a glorified clerical error. But that is precisely what happened.
Stupak had leased a section of a building at 2124 E. Carson Street from his friend of 25 years, Ambrose Lewis. A hotel operator, Lewis was called as a witness and had to admit that he had made space available in the building for what Stupak called his Yip-Yip Club. Lewis and other witnesses testified that, yes, Stupak definitely operated a dice game at the club. But no one remembered any illegal lottery.
“The Yip-Yip Club was a nice clean place where ordinary folks could come and try their luck,” Lewis said. His testimony began to take on the flavor of a testimonial for his old friend, Chester.
Had the witnesses known that the federal tax stamp was required for bookmaking and numbers, but not for craps?
A dice game violated state laws, but this was a federal case. Their collective memory proved most fortuitous for Chester. Although the press commonly called Stupak a numbers banker whose Pittsburgh empire encompassed the north and south sides of the city, he denied he was ever anything more than a dice dealer.
But the signs were right for conviction. Stupak had admitted paying off a police officer to protect a numbers network. The cop, John James, was on hand in an attempt to persuade a new jury of Stupak’s grave transgression.
With federal authorities such as U.S. Attorney General Robert Kennedy making big headlines for their pursuit of gamblers and members and associates of organized crime in the early 1960s, raiding dice dens became a favorite pastime of police and a popular editorial subject for journalists.
By January 1964, Chester barely had time to hang up his coat before hearing the cops at the door of one of his operations. In fact, it was his own coat that incriminated him after police used a steel-tipped battering ram to bust down the door of the converted Bauerlein Brewery. When the authorities got around to scooping up the dice, chips, cards, and tables, they also found a sports jacket no one was interested in claiming. The ever dapper Chester Stupak had left a laundry ticket with his name on it inside the pocket of the coat.
In late 1964, more than 18 years after Chester’s first gambling arrest, Federal Judge Herbert P. Sorg sentenced him to four months in prison, assessed a $2,500 fine, and placed the gambler on one year’s probation.
The legal assault was far from finished. In 1966, the Pennsylvania State Police hooked up with Internal Revenue Service agents, and Stupak was on the run again. Agents seized a $10,000-a-day numbers operation from a garage at the farm of Stupak associate William Donovan. Not only was Chester arrested, but police grabbed his nephew, James Stupak, as well.
Chester was as unflappable as ever. When confronted by the police, he shrugged and said, “This is the first time I’ve ever been here.”
But police had spotted him going in and out of the garage for weeks. He wound up serving six months in jail.
__________________
Bob Stupak saw first hand what operating illegally could do even to an accomplished angle-shooter like his father. Cross the line, and the authorities eventually will get you. Not everyone can be bought or cajoled. Even the best hustlers pay the price sooner or later.
Young Bob Stupak was nothing if not resourceful. For years he had noticed a decades-old racket that operated just inside the law. The hook was simple, really. An enterprising soul approaches restaurants, cafes, and nightclubs with a pitch: For the promise of discounts on meals and services, their establishment is included at no charge in a big book of valuable coupons offered to prospective customers. The restaurant owner benefits by the increased business and the consumer gets to eat on the cheap. The man who puts the two together makes money by selling the coupon books, with their estimated hundreds of dollars of value, for less than a sawbuck.
Stupak’s first book was a crude little number that offered discounts on goods, services, and entertainment from Pittsburgh’s “most respected” establishments. That is, those establishments he could enlist in his program. The first book featured $100 in value and sold for $6.95. It was immediately successful and led to more expansive versions that included free car washes, two-for-one meals, movie tickets, bowling, and beauty-parlor services.
“I’d put a book together, then go out on the road and sell it,” Stupak remembered. “I’d come home as soon as I built up a bankroll.”
Where motorcycles and nightclub singing had failed to provide him with the money his nonstop lifestyle and growing gambling habit demanded, the coupon books promised scads of fast cash. He quickly turned himself into the uncrowned king of discount coupons. Coupon books had been a Pittsburgh street business since the 1920s, but Stupak was well on his way to reestablishing the system and hustling it as never before.
Chester, of course, didn’t need to promote his business. His action was still wide open, which by the mid-1960s had begun to make Pittsburgh police and prosecutors more than a little nervous. Between election-year political grandstanding and federal revenue agents sniffing for scandal, smiling Chester Stupak was being squeezed. The beat cops might have wanted to ignore his second-floor crap game and countryside casino, but they could not ignore the presence of federal law enforcement. Once again they were forced to crack down on the Mayor of the South Side.
About the time Chester was convicted for the first time, Bob Stupak began making trips to Las Vegas.
“The first time I came to Vegas, it was ’64,” Stupak recalled later. “I sat down in a restaurant at 4 a.m. and the waitress said, ‘What are you having, sir? Breakfast, lunch, or dinner?’ It was 4 a.m., and she was asking, ‘Breakfast, lunch, or dinner?’ I thought, ‘God made this town for me.’
“That’s when I became absolutely mesmerized with Las Vegas. It seemed like the city was tailor made for me.”
But he would quickly learn another valuable lesson: Las Vegas was not a town for the impatient or faint of heart.
Bob Stupak began his Las Vegas education not long after that first visit. The occasion was a score with a coupon book worth $250 that he sold like crazy for $12.95. He was making plenty of money and decided to spend some. That meant a dice trip to Las Vegas. He packed a bag and grabbed the first early-morning jet heading west. He called ahead and booked a room at Caesars Palace, but by the time he arrived at McCarran Field a little after noon, his clothes looked like he had slept in them. At the airport, he laid out a couple hundred bucks and bought himself the classic Vegas-Guy uniform: wild sports shirt with an open collar, gaudy pants, and white shoes.
“After changing right there at the airport, I felt like an altogether different guy,” Stupak said many years later. “I was just excited about being there.”
Resembling a cross between a pimp and a professional golfer, Stupak hit Caesars running. He dumped his bags at the bell desk, toked the bellman, took out a $10,000 marker, and drank in the scene.
For men with the true heart of a gambler, the air is different in Las Vegas. For card and dice junkies, its alkaline waters are more rejuvenating than the baths at Lourdes.
Stupak hit the tables the way a boozer hits the juice.
And the tables hit him back.
Caesars Palace, the home of his hero Frank Sinatra and enough Wiseguys to fill a Hall of Fame mug book, was rapidly busting him out. He bet and lost, bet and lost, bet and lost, lost, lost.
“Soon I took out markers for everything I had, and I blew it all,” Stupak said. “I was flat busted—blew my credit entirely.”
The $10,000 gone, he shuffled back to the credit manager and managed to get another $2,000. In a few moments, he went quiet again. Now he was down $12,000.
It was not yet 1 p.m. He had been in Las Vegas less than one hour. It had taken him longer to get his bags and hail a cab to the hotel than it had to exhaust his entire credit line plus 20 percent. He felt as if every sharp gambler in the place was watching him.
“Here I was in my new clothes at Caesars, and I was flat broke,” he recalled in his 1985 book Stupak on Craps. “I didn’t even get to my room, didn’t have a drink, didn’t go to the bar, didn’t go to dinner, didn’t go to a show. I didn’t do anything. The only thing I did was get mad at myself, at Las Vegas, at the world.”
He returned to the bell desk, where the bellhop clearly remembered him and his $5 tip. After all, less than 60 minutes had elapsed. He ordered his bags, shook off the bellhop’s bewildered look, left the building, and refused to change his mind about leaving Las Vegas. His Vegas vacation had cost $12,000 plus airfare and had lasted all of an hour. At those prices, he couldn’t afford to change his mind.
He stewed over the loss all the way back to Pittsburgh and for days afterward. The Pittsburgh Kid had acted like the biggest sucker ever to chew a hayseed. He had tossed his accomplished money-management skills like snake eyes the minute he walked through the door. He had allowed the scent of the action and the speed of the city to cloud his thinking, something that happened to tourists, but was not supposed to affect a genuine wise-guy gambler like Stupak.
It was then he realized that the only way he was ever going to make a consistent score in a Las Vegas casino was to own one.
Bob Stupak’s life left little time for sleep. He dealt coupon books during the day, staked crap games after dark. The popularity of the coupons enabled him to generate fast cash and live a deceivingly high lifestyle. He drove a canary-yellow Cadillac with matching interior. When he pulled up to the Stardust Lounge in Pittsburgh with a date on one arm and a $2,000 wad of cash in one pocket, he never failed to be noticed. Other men scuffled for their livings, and the young Stupak seemed to come by his so easily.
It didn’t hurt that he peeled off a $100 bill and bought a round of drinks for the house. Surely his source of cash was as infinite as it was illegal.
In reality, everything he owned was either in his pocket, on his back, or in the trunk of the Cadillac. But there was no need to let anyone in on the secret, especially not the small-stakes crap-shooters who couldn’t resist taking a shot at the young punk with the yellow ride and the ready cash. So, he obliged them. He picked them up like school children, escorted them to the basement of his family’s Brownsville Road home, and cleaned them out as fast as he could. Then he drove them back to the Stardust, bought them a drink, and bid them goodnight.
“You couldn’t miss the car in those days,” he said. “I had $2,000 in my pocket and the Cadillac. As far as they were concerned, I had millions. It was all show business. Everybody wanted to take a shot. Why? Because I had the bankroll.”
And the patter to go with it. In a pinch, he made up rules as he went along, brushing off doubters with, “These are downtown Vegas rules.”
“I had a lot of fun with that,” he said. “I broke a lot of guys. And I got broke myself once. A bunch of guys cleaned me out of my whole fucking bankroll, then flew to Vegas and came back empty. Oh, that pissed me off. But most of the time it was okay.”
It kept him in spending cash, which he often deposited at the region’s racetracks. The horses didn’t always run his way, but as usual, Bob Stupak had an angle worked out that narrowed the odds against him considerably. He booked the bets of his pals, who spent freely and believed that, since Stupak was the youngest in the bunch, he ought to be in charge of running the wagers to the betting window. Instead, he handled the bets himself, disappeared until after the race was over, paid off the winners at track odds, and pocketed the losing bets. At Pittsburgh Meadows and Waterford Park, there was no easier way to make a small score.
“I never had a steady job,” Bob Stupak once said of his youth. “All the jobs I had were self-inflicted.”
If he had held a steady job, his life might have taken an entirely different course. While running the street, Stupak met and fell in love with Gerry Bova, the daughter of a Western Union worker. He bought her a two-and-a-half-carat diamond ring and the couple was engaged to be married. Instead of going down the aisle, though, the experience led to a trip halfway across the world.
“She said she couldn’t marry anyone without a job,” Stupak recalled.
Not long after that, Bob Stupak got into yet another motorcycle accident. He received a $3,200 insurance settlement and had a decision to make: he could either buy a new racing motorcycle or take his coupon book parade on the road. He decided to buy the bike, but it already had been sold to someone else.
By this time, not yet 24, Stupak was working a number of angles in Pittsburgh, but the town was growing too familiar. On the advice of his father, Bob Stupak struck out for Australia.
The son of a gambler could not have picked a more fitting destination. By some accounts, Australians bet more than any other English-speaking people. Whether on the two-up coin-toss, the annual Melbourne Cup race, or in one of a growing number of casinos, Aussies have always had plenty of ways to risk their money. Although not always lawful—two-up, for example, was illegal until 1983—gambling is woven into the fabric of the nation.
“Gambling is, quite simply, the national passion and the most obvious dislocating force at every level,” Australian author Richard Walsh once wrote.
Australian novelist Frank Hardy observed in The Four-Legged Lottery: “Gambling in Australia. Where else in the world are jockeys more revered than musicians or scientists? Where else in the world are the people’s clubs dependent for their existence on poker machines? Where else in the world is a famous racehorse stuffed and enshrined in a museum?
“… From the very beginning, life was a gamble among the convicts and settlers. Our country was pioneered in the spirit of a gambler’s throw.”
Years later, Stupak would put it simply. He wasn’t dodging the law or the draft when he set off for Australia.
“I wanted adventure,” he said.
With the $3,200 insurance settlement, plus a wad of cash from his father, Bob Stupak set out to conquer Australia one coupon- book buyer at a time.
“I went over on a shoestring, but I started making money almost immediately,” he said later. “I’ve just been very lucky in business.”
Lucky, but more than a little unorthodox by Australian standards. Aussie authorities had a devil of a time figuring out where all Stupak’s money came from—and where it was going. His accounting procedures were to say the least unusual and, more importantly, his method of paying taxes odd. Melbourne officials might have been new to the coupon game, but they knew plenty about taxes and were well capable of following a paper trail where one existed.
Stupak wasn’t the only American seeking fortune in Australia. Bally Corporation had sent its emissaries Down Under in an attempt to expand its slot machine empire. But Stupak’s goals were not quite as expansive. His coupon club was ideally suited to his cocky personality. He knew that he wasn’t really selling value to either the restaurant owner or the patron; he was selling the idea of value. And he was selling himself, which was fast becoming his greatest skill.
Victoria police were almost immediately suspicious of Stupak’s game, but as they watched his one-man empire grow, it became apparent that merchants and consumers were participating freely in his coupon program. His books, filled with two-for-one meal deals, were becoming increasingly popular, especially after he generated enough of a following to advertise and expand his discount services.
Years later, even the most experienced detectives with Victoria’s Major Fraud Group would recall no problems with Stupak’s program worthy of opening a large-scale investigation. Their files, in fact, failed to retain even his name.
The Melbourne Office of Fair Trade and Business, the city’s version of the Better Business Bureau, also gave Stupak a pass. The office, responsible for investigating illegal and unsavory businesses, had no record in its expansive database of Stupak, who was fast becoming known as the Yankee Invader in some Aussie circles.
His coupon books were catching on, but Stupak was impatient. He wanted the success to come more quickly and was encountering opposition from Australian business owners who were reluctant to trust a Yank. So he enlisted chapters of the Junior Chamber of Commerce in cities across the country to participate in his “Business Sampler” program, which not only offered the usual goods-and-services coupon pitch, but also generated income for the service organizations.
He accomplished this feat in a way that, by late-1960s standards, was nothing short of progressive. Instead of the usual face-to-face sales meetings, in which his youthful appearance and Junior Elvis wardrobe were bound to alienate some skeptics, he produced a movie that extolled the vast virtues of the Business Sampler program. The self-produced soundtrack was hip, the voice-over respectfully Australian. The star, of course, was Bob Stupak.
And it worked.
From Adelaide to Sydney, hundreds of businesses warmed up to his snazzy coupon pitch. Sitting at the top of the pyramid, he raked in the cash.
As in Pittsburgh, the money came and went. He threw lavish parties, ate at the best restaurants, tipped a week’s pay, and established himself as an American playboy.
The major criticism of Stupak’s operation was the loose accounting. He was, after all, the son of a backroom casino man who kept the day’s winnings in his head and hip pocket. Though it was no sin in the Australia of the late 1960s, such shoddy practices would qualify as trouble spots when he eventually moved back to the United States and attempted to open a casino in Las Vegas.
Stupak traveled widely through Australia during the seven years he made it his home. It was there he met and became infatuated with Annette Suna. In his mid-20s, he was more interested in making money than settling down, but when Annette became pregnant, he found himself faced with a tough decision. He thought of moving on, even returning to the United States, but instead the young hustler couldn’t leave behind the woman who carried his child.
“I was Catholic and so I did the Catholic thing,” Stupak recalled years later. “I married her.”
It wasn’t an understated elopement, but a grand affair. Stupak was in love with the camera and managed to finagle permission from authorities to shoot footage for the wedding movie from the top of the Sydney Harbor Bridge. After the wedding, the Stupaks embarked on a world tour. They traveled in style from the tropics to Europe. Bob Stupak’s ingenuity and eighth-grade education had taken him around the world at an age most young men were just getting out of college.
He was 25. His daughter, Nicole Stupak, was born several months later. Both Bob and Annette knew the relationship would not last; they were married less than two years. But Bob was proud of his baby girl and promised to remain in contact. Years later, Nicole Stupak would go to work for her father in Las Vegas.
While living in Australia, Stupak also met the woman who would become his second wife, Sandra Joyce Wilkinson. Blond-haired and outgoing, she adored the infinitely confident American who courted her. Sandy Stupak eventually would emerge as a fixture at the Las Vegas poker tournaments to which Stupak would become addicted. (She was nicknamed “Lady Maverick” after winning a high-stakes Texas hold ‘em poker game in 1984 at Binion’s Horseshoe.) Like many of the women in Bob Stupak’s life, she was seen as a classy, calming influence, albeit an ultimately unsuccessful one. Stupak married her in 1971 and they remained together until 1985. She gave him two children, Nevada and Summer, and supported his wild acts of self-promotion.
“Bob has always been Bob. You know, rough around the edges and as cocky as can be,” a longtime friend of Stupak recalled. “But Sandy, she was a nice lady. She knew how to act in public. And I think she had a head for figures. She wasn’t obnoxious, as Stupak could be on occasion. I think she did her best to complement him, but that wasn’t always easy. Bob could be pretty wild, drinking and carrying on. With Bob, you never knew which set of manners he was going to bring with him. But Sandy, she was a nice lady. Pretty, too.”
Bob Stupak resided in Australia off and on for seven years before returning to Pittsburgh. All the while he dreamed of going back to the Strip and breaking into gambling’s major leagues. By 1971, he had plenty of Australian dollars to exchange and big plans for a casino of his own. But it would take more than a bankroll and bravado to make it in Las Vegas.