Even if the racketeers refrained from coercing the fighters themselves, they exerted considerable influence over the sport through gambling. Whenever Ross fought, for example, many people from his neighborhood hocked their valuables in order to place the largest possible bet on him. “Al told me I was his good-luck charm,” Ross recalled. “ ‘I made a lot of money betting on you, kid,’ he said. ‘I’m gonna keep betting on you every time you fight.’ ” When Ross cautioned that he couldn’t win them all, Capone shrugged. “ ‘So what? You’re our neighborhood boy. We gotta back you, win or lose.” But once, when Al thought Ross was dogging it in the ring, he took the boxer aside and lectured him: “What the hell’s the matter with you, kid? I hear you spend your nights running to every lousy joint in town. Take it from me, you’re a goddamn dunce.” Ross heeded the warning and won his next decision.
Although Ross and the other fighters hotly denied that the gentlemanly racketeers or the managers they controlled ever fixed fights, evidence to the contrary abounded, especially in Chicago, where the Capone syndicate often dictated who fought whom and what the outcome would be. Their principal connection to the fight world was Joe Glaser, best remembered for managing the career of Louis Armstrong. In an earlier incarnation Glaser was an influential fight promoter in Chicago. From his two-room office in the Loop, Glaser ran his boxing empire and zealously protected his turf. When a gambler and part-time journalist named Eddie Borden denounced Glaser in print as a front for the Capone organization, Glaser had the man run out of town and swiftly returned to business as usual. Glaser’s power to fix fights earned him a reputation as the sage of boxing, especially among reporters. Vern Whaley, who covered boxing for the Chicago Evening Post, recalls that “on the day of a big fight card at Mills Stadium, Comiskey Park, Cubs Park, even at Guyon’s Paradise Ballroom on the west side, Glaser would give me the names of the winners in advance, even the round of a knockout in some bouts that were obviously fixed.” Equipped with the leads supplied by good old Joe, Whaley developed a “sensational record” for picking probable winners in his newspaper column.
Among the fighters in whom Capone took an interest was his former caddie, Timothy Sullivan, who had matured into a young boxer of promise. Capone came to watch him work out in local gyms and later on arranged fights for Sullivan—nothing major, no real money involved, just club fights. He eventually compiled a respectable but hardly spectacular 22-19 record.
• • •
The custom of fixing fights went from being the scuttlebutt of newsrooms and gymnasiums around Chicago to an issue of national concern in September 1927. The occasion was the Jack Dempsey-Gene Tunney bout for the heavyweight championship of the world. It promised to be the biggest boxing spectacle ever held in Chicago, and Capone, who loved boxing, was in the thick of the action. Al had become acquainted with Dempsey shortly after the Manassa Mauler (after his hardscrabble birthplace, Manassa, Colorado) had decked Jess Willard to win the title in 1919. And Dempsey considered Al to be “one of my number one fans.” Their relationship had been conducted in secret, however; when Capone visited Dempsey’s training camp, cameras were averted and reporters put down their notebooks. But Dempsey felt comfortable with Capone, who earned his qualified admiration: “He was a rough customer who wanted to be accepted as a man, not a racketeer.”
Dempsey became a controversial figure not for associating with Capone but for refusing to defend his title between 1923 and 1926 against a worthy challenger, Harry Willis, who was black. Instead, Dempsey chose to fight Gene Tunney, who was white and weighed the same as Dempsey: 190 pounds. The New York Athletic Commission withheld its blessing because Dempsey had refused to fight Willis, so the Dempsey-Tunney bout took place in Philadelphia. Tunney prevailed and became the new heavyweight champion. Soon after, Dempsey asked for a rematch. Tunney agreed, and the bout was scheduled to take place at Soldiers Field in Chicago on September 22, 1927. It was to be among the most publicized and controversial contests in boxing history.
Weeks in advance stories swirled through Chicago that Capone was making every effort to ensure that his pal won this time out. It was said that Capone bet $50,000 on Dempsey. He also bought one hundred ringside seats at $40 apiece for his friends and colleagues, and his organization bankrolled countless other bets on the fight. Stories of Capone’s involvement with Dempsey became so widespread that the Manassa Mauler was forced to address them publicly; he explained that he asked his friend Al to keep his distance in the name of “sportsmanship.” For the sake of appearances Capone reversed himself; now all bets were off. “He’d better get a square shake,” he told another fight promoter, “Doc” Kearns, concerning Dempsey. “Nothing preferential, understand, but a fair shake.” At the same time he sent Jack and his wife a lavish bouquet bearing a message: “To the Dempseys, in the name of sportsmanship.”
This being Chicago, Dempsey arrived at Soldiers Field on the day of the fight in a bulletproof car under heavy police escort. Capone arrived in the company of a taciturn journalist. The man was carefully attired in an understated suit, his face highlighted by wire-rimmed glasses and a narrow, thin-lipped mouth. Few recognized his face, but everyone there read the columns he wrote for the Hearst papers and instantly recognized his name: Damon Runyon. Preferring to talk with his typewriter rather than his mouth, Runyon was fond of observing gangsters at close range, not to expose them, but to view the world with the moral astigmatism of the inveterate racketeer. Damon Runyon was himself a Damon Runyon character—a hard-bitten, hardworking, hard-boiled man who held the world at arm’s length. Isolated from friend and foe alike, he was in the midst of transforming himself from a columnist and sportswriter into one of the most highly paid short story writers of the day, using his gangster pals as models. Runyon’s colorful gangsters reeked of romance and cockeyed charm, and his suave amorality became his trademark. Thus Al Capone—with his big mouth, his cigar, his bizarre flights of generosity, megalomania, and paranoia—became one of the best Damon Runyon characters Damon Runyon ever met.
Runyon and Capone were joined that night by 145,000 other boxing fans. As Dempsey’s emphasis on “sportsmanship” suggested, boxing was aiming for respectability and the Jazz Age was prepared to confer it; this was, for instance, the first major bout at which women formed a significant part of the crowd. “They came in, smiling a bit self-consciously, made themselves pretty, chatted through the preliminary bouts, bit their lips and twisted their mouths,” observed the reporter for the Chicago Tribune, Genevieve Forbes Herrick. “They wanted a knockout, O, without too much blood, but a knockout.”
The great event was preceded by the appearance of the three most powerful elected officials in Illinois: Governor Len Small, Mayor William Hale Thompson, and State Attorney Robert Crowe. “They stood in the white glare of the forty-five huge lamps that made ring and ringside a blaze of daylight and smilingly received the cheers of jubilant men and women,” wrote a breathless reporter. At his ringside seat, Al Capone joined the applause, and although the officials ignored him, it must have been comforting for him to reflect that he, the man in the dark, owned all three of the men looming above him in the light, and through them exercised greater influence than any other individual in Illinois.
At 10:00 P.M. the pudgy politicians at last yielded the ring to the fighters, and a sense of expectation at the great contest that was about to begin energized the crowd. The gong sounded, and the fight finally commenced, Dempsey in the dark trunks and Tunney in the white. Dempsey had let his beard grow, and he looked, said one reporter, “savage.” The two started sparring, more concerned with not losing than with winning, and as the fight proceeded there was a faint murmuring of disappointment in the crowd as the hoped-for knockout punch failed to appear. But it was clear that Tunney was outfighting Dempsey, the man whom Capone had befriended and backed.
In the middle of the seventh round, Dempsey smacked Tunney’s jaw three times in brutal succession, and Tunney, a “crazy, glassy look in his blue eyes,” fell to the
floor, “like a drunken man.” As Tunney grasped one of the ropes to try to steady himself, Dempsey, arms outstretched, towered over him. Tunney gave no sign of returning to his feet. The referee, Dave Barry, tried to wave Dempsey away so the count could begin, but Dempsey, who was himself disoriented, spent perhaps five precious seconds hovering above Tunney, inadvertently delaying the count. Finally he lumbered to his corner, and the referee began the ritual, which was overwhelmed by the deafening howls of the crowd. “By the time the count was under way Gene’s head was beginning to clear and before it had progressed half way he had managed to raise himself to sitting position, ready to get up when the count of nine was reached,” noted a ringside observer. This moment of suspended animation became known as the legendary “long count,” subject of endless debates and hairsplitting over the rules, but in the end all that mattered was that Tunney did get to his feet. Fighting cautiously, he managed to knock down Dempsey in the eighth round, and he was still standing at the end of ten. Tunney won the match by a unanimous decision and retained his title as the heavyweight champion of the world.
After the fight, Capone returned to the Metropole, where he threw a lavish party at which senators and congressmen mingled with journalists eager to drink Al’s free booze and with society figures who were in turn desperate to rub elbows with real gangsters. There was a band, of course—this was the Jazz Age, and there was always a band—conducted by Jule Styne, a former child prodigy who had abandoned the strictures of classical music for the popular realm. Later known for his Broadway songs and Hollywood scores, he was now leading a dance band. After the musicians warmed up, Capone took over from Styne, prepared to display his familiarity with Gershwin’s “Rhapsody in Blue,” the sinuous anthem of the Jazz Age itself.
Al Capone planned to conduct. He had a baton, he had the sheet music, and he had the attention of everyone in the room. He waved his arms with a confident flourish—as if to say conducting was easy, anybody could do it—and the band played. Under the gangster’s direction a clarinet soared, the piano trilled, and a recognizable rendition of Gershwin’s famous music filled the Metropole. And when his rhapsody ended, Capone took a bow and surrendered his baton. It had been a memorable fight, and for the audience at the Metropole that night, an even more memorable concert.
For Capone the fight marked another glorious night in Chicago, a night to make the twenties roar, but for Jack Dempsey, the loss marked the end of his championship aspirations. He was still useful to Capone, however. When the Manassa Mauler retired from the ring, he went to work promoting fights for the Capone organization. But fixed fights were still the order of the day in Chicago, and as Dempsey later wrote, “I quit because I was being used as a front, a promoter in name only. . . . Capone’s mob wound up telling me who was going to fight and how much I had to pay them. When they started giving orders who was going to win and who was going to lose—and naming the round—I got out.” Although Dempsey broke with the Capone organization, he later entered into a partnership with Meyer Lansky and Longy Zwillman, two prominent Jewish racketeers, to run the Dempsey-Vanderbilt Hotel in Miami Beach, Florida.
• • •
Closer than ever to attaining the respectability he craved, Capone expanded his organization. Within months of Thompson’s arrival at City Hall, the Chicago Crime Commission discovered, “Capone took over the south side, with all privileges. His man [Jimmy] Mondi opened a gambling joint on Clark street, south of Madison street. . . . Capone took over the beer territories from the Saltis and O’Donnell gangs. The slot machine racket later involved the indictment of six police captains. Capone got more than the $260,000 back.” He exercised greater control than ever before over the Police Department; the upper echelons of the force aided the racketeer in maintaining a continuous flow of whiskey, even as cops on the beat conducted raids designed mainly for show. William Pasley, a reporter covering Chicago’s renewed corruption, grumbled, “Watching an official with a gold star on his chest comfortably downing snits of whiskey while his men are out dryraiding the city is a rare experience.” Capone’s near-monopoly of Chicago gambling and bootlegging, the booming economy, and the complete disregard of Prohibition drove the organization’s revenue to new heights. In 1927, the U.S. attorney’s office estimated, the Capone combine took in approximately $105 million. The amount broke down as follows:
Alcohol manufacture and sale
$60,000,000
Gambling
25,000,000
Vice and resorts
10,000,000
Other rackets
10,000,000
1927 had been a good year for the Capone organization, even with Al in retirement much of the time, and 1928 promised to be even better.
Violence returned to Chicago, for Thompson’s new order upset the fragile truce among racketeers engineered by Capone. In May, hardly a month after Thompson took office, a series of murders—there would be four in all—stymied the police. In every case, the victim was attired in the snappy garb favored by racketeers and carried a substantial bankroll, which had not been disturbed. In addition, each victim was Italian, and each came from out of town, one from New York, two from St. Louis, and one from Cleveland. More peculiar still, the right hand of each victim held a nickel; the coin had apparently been placed there after the shooting. The police interpreted the placement of the coin to be a gesture of utter contempt, as if to say the victim’s life wasn’t worth a nickel.
Suspicion fell on three men associated with the Capone organization: Scalise and Anselmi, who always worked as a pair, and “Machine Gun” Jack McGurn. Notorious assassins, Scalise and Anselmi made likely culprits, but the nickel suggested a flourish beyond their primitive methods for dispatching their victims. Jack McGurn, now a rising star in the Capone organization, strenuously denied any knowledge of the murders. Yet McGurn’s word was never reliable. Of all Capone’s gunmen, he was the most complex and unpredictable, more of a lethal prankster than a hired assassin: able, smart, and mercurial. Vincenzo Gebaldi (McGurn’s real name) was a Chicago boy, the oldest of six, a product of Little Italy, where he distinguished himself both as a student and as a pugilist. He rose through the ranks of amateur boxing clubs, shed his Italian name in favor of a more commercially acceptable Irish nom de guerre, and as Jack McGurn established himself as a welterweight with promise. At about this time, McGurn’s father, Angelo, a grocer, developed a sideline selling sugar to the Gennas, the leading alky-cookers of Little Italy. Although this alone did not make Angelo a gangster, he was dealing with exceedingly dangerous men, and in January 1923 he was shot to death. Jack McGurn was nineteen at the time. He turned to a life of crime soon after his father’s death, and the police became familiar with him through a variety of violent escapades; he was even wounded by machine gun fire, but he survived to become known as “Machine Gun” Jack McGurn and to carve out his bloody niche in the Capone organization. Despite his reputation, he avoided arrest, and he maintained his innocence throughout the police investigation of the four well-dressed men found dead with their bankrolls intact and nickels pressed into their palms. Although the police ultimately failed to tie McGurn to the murders, they remained deeply suspicious. Had they known him just a little better, they would have realized that when his father, Angelo, was found dead on the streets of Little Italy, he, too, clutched a nickel in his right hand.
All the corpses found during this period had one thing in common: they had once been men who had tried to win the bounty placed on the head of Al Capone. It had not been put there by the police, of course, but by yet another rival, Joseph Aiello, rushing to fill the vacuum created by the death of “Hymie” Weiss and “Schemer” Drucci. Aiello came from a large Sicilian family; in fact, the Aiello clan was in many ways the successor to the Gennas in the Little Italy alky-cooking trade, which is to say they were extremely dangerous. Capone feared them, for the Aiellos had put a bounty on his head: $50,000, they said, for the life of Al Capone. As McGurn eliminated one would-be assassin after
another, the Aiellos tried a different approach. They kidnapped the cook at one of Capone’s favorite restaurants, the Bella Napoli, and offered him a simple proposition: either be killed or poison Al’s next meal in the restaurant with prussic acid. Should the cook accept the latter proposition, Joseph Aiello offered $10,000 to show his appreciation. The cook displayed keen business sense by agreeing to the plan, insisting on payment up front, and then rushing to tell Capone of the Aiellos’ perfidy at the first opportunity, thereby endearing himself to his best-known customer. In response, Capone immediately declared that Aiello must be eliminated. Now desperate, Aiello devised another, far more serious attempt on the life of his adversary.
To the casual observer, 311 South Clark Street was a nondescript cigar store in a crowded, unpretentious Chicago neighborhood. But as Aiello and every other racketeer knew, the store served another function as the headquarters of corrupt politicians who controlled the First Ward. It was at this address that “Hinky Dink” Kenna managed his network of payoffs, and it served as a meeting place for politicians and racketeers, including Capone. Across the street stood the small Atlantic Hotel, where, in room 302, Aiello established a machine-gun nest, which meant, in practice, two or three gunmen sitting barely concealed behind draperies in front of a window, scanning the street hour after hour, waiting for their prey.
Capone’s obvious move would have been to send his men in after Aiello’s crew, but the notoriety resulting from a gun battle between two rival gangs was exactly what he wished to avoid. Instead, he employed his connections in the Police Department to deal with Aiello. In place of Capone henchmen appearing at the Atlantic Hotel, a group of policemen broke up the machinegun nest, then arrested Aiello in his home in Rogers Park on November 22, 1927. The cops brought him to the Detective Bureau at 1121 South Street for questioning; shortly after he arrived, however, the police tipped off Capone. As Aiello prepared to leave the building, a fleet of cabs raced to the Detective Bureau, and when they arrived, their brakes squealing, over a dozen Capone gunmen hit the street, some equipped with machine guns, others with .45-caliber automatics. So efficient and organized did they seem that policemen observing the sight took the arrivals to be detectives, not gangsters. Only when one of the men entered the Bureau and was recognized as Louis “Little New York” Campagna, a Capone gunman, did the cops realize the truth.
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