Scarface and the Untouchable

by Max Allan Collins

  Still, when Judge James H. Wilkerson brought him to trial on April 9, Ralph felt shocked, even ambushed.

  “This is Jim,” a voice said, in a call Seager overheard that evening. “Did you see what they did to Ralph?”

  “Why no,” said a feminine voice. “Was he hurt?”

  “Oh no, in court, they double-crossed him,” the caller said. “It was supposed to be all fixed up and they pulled a jury on him this morning.” In gangster-speak, jury might have been a concealed weapon.

  “Why, the rotten skunks.”

  “He is liable to get from three to ten years and a $10,000 fine.”

  “Isn’t that a shame.”

  Murdock’s rather lame defense insisted his client rushed to pay his back taxes as soon as illegal income became taxable—seemed as a “poor race-horse man,” Ralph couldn’t afford to settle up. The life of a gambler, after all, came with constant financial upheaval.

  The prosecutors brought in reams of evidence attesting to Ralph’s wealth. They ran through all the checks, deposit slips, and aliases the Intelligence Unit had uncovered. Witnesses testified Ralph sold beer—real beer, not the watered-down legal stuff he peddled mostly as a cover. Workmen wheeled piled bank records into the courtroom on hand trucks.

  “What are those?” Judge Wilkerson asked, as another hand truck rolled in.

  “More records,” a prosecutor said.

  The end came April 25. After two and a half hours, the jury found Ralph guilty on all counts. Bottles had finally surpassed his brother, becoming the first Chicago gangster ever convicted on tax charges. Shaken by the verdict, he strained to smile as he left the courtroom.

  Federal officials rejoiced. Assistant Treasury Secretary Walter Hope forwarded a clipping on the conviction to President Hoover: “The enclosed represents a little progress even though the chief offender still goes unapprehended.” At a press conference not long after, Hoover said his administration planned to use Ralph’s conviction as the springboard to “reach” his more notorious brother.

  Meanwhile, Youngquist kept pestering George Johnson to go after Capone, but Johnson refused to be rushed—he had “many lengthy cases” he refused to compromise, and Capone had been delayed accordingly. To speed things up and clear the backlog, Johnson asked the Justice Department to send more judges. That wasn’t what Youngquist wanted to hear, and he made sure the president knew the delay wasn’t his fault.

  “I impressed upon [Johnson] the one big job was to convict Al Capone for violation of the law,” Youngquist told Hoover, adding, “I wanted you to know we are keeping after it.”

  Despite a clogged caseload, Johnson wasn’t finished with Ralph. By early May, Alexander Jamie and the special agents had linked Bottles to a massive international smuggling plot.

  Most Canadian booze came into the country by truck or boat, but the Capones had adopted a new vehicle, the airplane. Six times a week, their men flew cases of Johnnie Walker and Old Smuggler, worth $50 in Canada, from Windsor, Ontario, to an airfield near Cicero. When the planes touched down, the liquor’s value doubled. The Outfit had smuggled in about fourteen thousand cases over the past eight months, with a street value of $1.4 million. Then they cut the liquor with pure alcohol and artificial flavors, stretching profits even further. They may also have been smuggling drugs by air.

  Jamie raided the Cotton Club and Greyhound Inn in the early morning hours of May 8. First the special agents hit the Cotton Club, well-dressed patrons packing the place as the feds stormed in, creating chaos. But the lawmen left the customers alone, arresting only employees and seizing some important-looking records.

  The raiders moved on to the Greyhound Inn, where they arrested a waiter and a bartender. Ralph was conspicuously absent, but his attorney called Jamie later that day and promised to bring his client in for arraignment.

  Just hours after Bottles left the Federal Building, the special agents struck again. This time Ness led his own raid on the Cotton Club, hitting it at its peak capacity. Club manager Percy Haller, arrested in the earlier raid, lost his patience. As Ness picked up a highball and went to pour it into an evidence bottle, Haller knocked the glass out of his hand, and got taken in for resisting a federal officer and obstruction of justice.

  On May 28, the grand jury handed down indictments against Ralph, Haller, and seven associates, including a doorman at the Cotton Club known only as “Rasputin,” on conspiracy to violate the Volstead Act. Under the newly enacted Jones Law, mandating stiffer sentences for Prohibition violations, Ralph faced five years in prison and a $10,000 fine.

  But these cases would never go to trial. From Johnson’s point of view, the potential result wasn’t worth the Herculean effort. Until he got his wish for more judges, he had to think carefully about where to invest precious time and resources.

  Johnson already had Ralph on tax charges, and the chances of convicting him again seemed slim—juries rarely found anyone guilty of bootlegging. And with the Hoover administration clamoring to bag Ralph’s younger brother, harassing the gangsters and exposing their secrets seemed enough—for now.

  With these parallel investigations into Ralph’s affairs, Johnson had developed the strategy he would use against Capone. While the Intelligence Unit worked to build another tax case, Jamie’s special agents would smash the Outfit’s breweries and distilleries, bedeviling the gang and drying up its income.

  Jamie’s men would also gather evidence for more liquor conspiracy cases, because whether investigators could hang a tax evasion charge on Capone remained to be seen. Ralph had left no shortage of evidence of tax fraud, but his brother had been much more careful. Johnson needed to keep his options open.

  In mid-June, Judge Wilkerson sentenced Ralph Capone to three years in prison and a $10,000 fine. Bottles got out on bond, pending appeal.

  As the marshals led him away, someone heard Al’s brother remark, “I don’t understand this at all.”

  He’d sounded tougher on the phone, pushing underlings around.

  “There is nothing of much interest to report in connection with the Al Capone investigation,” Art Madden, special agent in charge of the Chicago Intelligence Unit, wrote to Elmer Irey shortly after Ralph’s conviction.

  Madden had a hunch Capone took a share of the proceeds from the Hawthorne Kennel Club, a Cicero dog-racing track, but couldn’t prove it. Profits from the track passed through the Roosevelt Finance Company, a money-laundering operation run by Frank Nitto’s old associate, Alex Greenberg. After that, the trail grew muddy.

  “As a matter of fact,” Madden wrote, “there is fairly convincing proof that substantial sums were paid to Frank Nitto, who is one of the principals in the Capone organization.” To gather more evidence, Madden intended to question “the head of the dog track, a man named O’Hare,” who had “already been before the Grand Jury.” Madden advised “a more determined effort” be made against this O’Hare.

  The special agent didn’t know it yet, but he’d found the lead that would break the case wide open. The man he knew as the “head of the dog track” was Edgar Joseph O’Hare, a fast-talking, clean-living lawyer from St. Louis. Charming, cultured, and athletic, O’Hare was a family man who doted on his only son, Edward, nicknamed “Butch.”

  As an attorney, O’Hare had come to control the patent on the mechanical rabbit used in dog races, soon growing wealthy licensing the device to racetracks. His success caught the eye of the Outfit, which liked dog racing because it was easy to fix. All they had to do was overfeed the dogs they wanted to lose.

  The Outfit opened its own track in Cicero near one run by O’Hare, without paying for use of his rabbit, hoping to run him out of business. The spunky lawyer threatened legal action.

  “If I can’t operate in Chicago,” he warned the gangsters, “then nobody can.”

  Capone, perhaps impressed by the entrepreneur’s pluck, offered a partnership. O’Hare accepted, Nitto working out the deal. They’d all earn a fortune, but O’Hare made a show of scorning his
partners. “You can make money through business associations with gangsters,” he claimed, “and you will run no risk if you don’t associate personally with them. Keep it on a business basis and there’s nothing to fear.”

  To his daughter, O’Hare declared, “I have never accepted so much as a bottle of beer from the gangsters with whom I must do business because one cannot accept anything, no matter how small. . . . If you do, they have you.”

  Despite his lily-white front, O’Hare was no angel. An exceedingly sharp slickster, he possessed an unmatched talent for finding holes in the law, earning the nicknames “Fast Eddie” and “Artful Eddie.”

  He also had a history of double-crossing his friends. In the early 1920s, O’Hare partnered with George Remus, the nation’s most successful bootlegger, in purchasing a Jack Daniel’s distillery in St. Louis. Remus doled out whiskey “for medicinal purposes,” while secretly diverting much of it into the illegal beverage market—essentially stealing from himself.

  But “Artful Eddie” did him one better. While Remus was in prison, O’Hare siphoned off some thirty thousand gallons of his partner’s whiskey and sold it to bootleggers in New York and Chicago, filling the emptied barrels with water. Remus learned of this when O’Hare was indicted on Prohibition charges, and his testimony helped get “Fast Eddie” convicted in 1926.

  True to his nickname, O’Hare squirmed out of serving time, paying Remus $250,000 for the looted liquor, after which Remus withdrew his testimony, winning O’Hare a reversal on appeal. Then O’Hare reportedly cut Remus in on the profits from Capone’s dog track.

  Madden and the Intelligence Unit tried unsuccessfully to trace those profits back to Capone.

  Then on May 9, Madden informed Irey about government securities the Roosevelt Finance Company had passed through to Capone. Madden was convinced O’Hare was the source—prove that, and they had the makings of a case against Capone, a real paper trail to big income the Big Fellow paid no tax on.

  But before the tax men could act, a pair claiming to be government agents raided the Roosevelt Finance Company and seized all important records. Then the “agents” disappeared, taking with them evidence crucial to the government’s case, and any hope of linking Capone to that line of income.

  Undeterred, Madden focused squarely on O’Hare, telling Irey he wanted to look into the lawyer’s tax situation. Irey met with his superiors, who found this lead promising enough to put their best investigator on the case—Frank John Wilson, forty-two, special agent with the Intelligence Unit out of Baltimore.

  Wilson had already worked in Chicago, building tax cases against bootleggers Terry Druggan and Frankie Lake. On a recent visit, he’d helped comb through Ralph Capone’s bank records, and sat in on a meeting with Mattingly discussing brother Al’s tax situation.

  Irey knew this agent—relentless and determined, as cold and gray as a January day—was the only person who could follow the money from O’Hare to Capone. “Wilson fears nothing that walks,” Irey wrote, nor did tedium deter him: “He will sit quietly looking at books eighteen hours a day, seven days a week, forever, if he wants to find something in those books.”

  Wilson’s doggedness sprang from the frustration of failed ambition. His father had been a cop, and Frank wanted nothing more than to be one, too. But, severely nearsighted, he couldn’t be trusted with a gun—bad eyes bounced him out of the army, and during the Great War he’d settled for working as an investigator with Herbert Hoover’s Food Administration.

  Did Wilson feel the need to compensate—to be tougher, rougher, and stronger than anyone on the battlefield? Perhaps. In the Intelligence Unit, his ruthlessness, and not just his financial acumen, set him apart. One colleague said, if so assigned, “Wilson would investigate his own grandmother.” A crook who had the misfortune of crossing Wilson’s path said the investigator “sweats ice water.”

  Yet the balding, bespectacled, somewhat stocky Wilson might have been an insurance salesman. He spoke stiffly in flat, nasal tones and smoked cheap cigars, shrouding himself in a foul haze. When he threatened to use his “regulation forty-five,” he meant the forty-fifth volume of Internal Revenue regulations, not his sidearm.

  Wilson knew how to break men down psychologically—to brutalize them not with fists, but with facts. And he never let up till he got what he wanted. Seeing Wilson in action, Adela Rogers St. Johns wrote, “A year—ten years—twenty years—you would never be safe, never be out of reach. . . . You could no more shake him nor reflect upon his honesty or his sureness of his facts than you could melt a glacier with a blow torch.”

  Wilson took charge of the Capone tax case in late May, after arriving in Chicago with his wife, Judith. He made sure she had no idea why they were in town.

  “There are some things you can tell a woman,” Wilson wrote, typically for his era, “and some things you can’t.”

  Not wanting to worry her—or, worse, have her drag him back to Baltimore—he lied about the case, saying only that he’d been ordered to start “investigating some politicians.”

  Then Wilson set out to get the lay of the land. Early on he learned that Alfred “Jake” Lingle, a crime reporter for the Tribune, knew more about the Outfit’s operations than just about anyone outside the organization. It was said Lingle counted Capone as a personal friend—though at present the two were on the outs. Wilson sensed a potentially valuable informant. In early June, he met with an attorney and an editor at the Tribune, who offered to put him in touch with the legman.

  Wilson had his first major lead.

  Jake Lingle’s final scoop, June 9, 1930.

  (Authors’ Collection)

  Seventeen

  June–August 1930

  Chicago’s train stations were often grand, but not Randolph Street Station, where the Illinois Central Railroad joined commuter lines to the South Side and working-class suburbs where the Outfit provided beer, gambling, and women.

  To access Randolph Street Station, you disappeared down a wide stairwell outside Chicago’s main Public Library, a splendid stone edifice with marble interiors—but the reading material chosen by commuters more likely came from the large newsstand nearby. This was where, on June 9, 1930, Tribune reporter Jake Lingle, thirty-eight, on his way to catch an early afternoon train, paused to make a selection from rival papers, racing forms, and pulp magazines.

  A former street kid with an elementary school education, reporter Lingle never wrote a word for publication—that was left to rewrite men. From a childhood friendship with beat cop Bill Russell, Jake picked up an easy way with police and their subculture, which proved invaluable as he worked his way up from office boy to budding crime reporter. He would drop by station houses and trade cheap cigars for tips.

  “He knew all the coppers by their first names,” Fred Pasley wrote. “He spent his spare time among them. He played penny-ante with them. He went to their wakes and funerals; their weddings and christenings.”

  As his closeness with the police grew, so did an acquaintance with “that nether stratum of society, the underworld.” Lingle met these tough boys in cells and poolrooms and speaks, on good terms with many, including the bosses. They became an inside source of gangland gossip.

  Once on a streetcar with his fiancée, he was jostled and knew right away his wallet was gone; but he also knew just what West Madison Street bar to go to, to retrieve it.

  He retained a street kid’s charm throughout his Tribune career, his moon face wearing a persistent grin pierced by an ever-present cigar (now in the three-for-half-a-dollar range). Yet the eyes in the boyish face of this thickset man were as old and tired as time. His curly hair thinning, his complexion dark, cheeks rosy—well tailored, well manicured, well barbered—this was a newspaperman as skeptical and vaguely sinister as any Hecht and MacArthur would serve up in The Front Page.

  Unlike many crime-beat reporters, he didn’t carry a gun and held the drinking to an occasional beer. But in one word—“Yeaaah?”—he could serve up a lifetime of cyni
cism. Still, most considered him a friendly sort, bighearted, even generous. As writer Walter Noble Burns put it, “Just a happy-go-lucky, roughneck West Side kid.”

  Shortly before he picked up a racing form at the newsstand outside the train station stairs, Lingle took a late breakfast at the Hotel Sherman coffee shop, where in the hotel lobby he spoke to a police sergeant.

  “I am being tailed,” Lingle told his friend.

  The sergeant looked around, saw no apparent hoodlums, and shrugged it off.

  As Lingle was about to head down the stairs to the train station, someone from a roadster at the curb called out, “Play Hy Schneider in the third race!”

  Lingle turned and said, “I’ve got him!” and started his descent.

  Had this seemingly friendly exchange been the way to confirm the reporter’s identity?

  Like so many others this time of day, Jake’s destination was the Washington Park racetrack in the far south suburbs, via the 1:30 P.M. express. There he could mix business and pleasure, hobnobbing with crooks and politicos, picking up leads. In the tunnel under Michigan Avenue emptying into the station’s low-ceilinged underground chamber, Jake was already checking his racing form, oblivious to two men who’d also paused at the newsstand. The pair—a tall, boater-hatted blond and a shorter, darker guy—hustled down the stairs and closed in on Lingle.

  The blond shoved a revolver behind Lingle’s head and squeezed off a round. Jake didn’t live long enough to hear the echo. The reporter who never wrote anything belly-flopped to the concrete, his latest cigar gripped between his lips, racing form like a hymnal in both hands, head spilling blood and brains.

  The blond paused, flung the Colt .38 snub-nose by the body, and about-faced to a side tunnel leading up to Michigan Avenue. The short, dark man kept going straight ahead. The shot reverberated through the tunnel, hundreds hearing it, but only a few near enough to see Lingle drop and the assassin depart. Two witnesses took chase, following the blond up the stairs to the street, where they saw him dash through the bustling intersection at Randolph and Michigan, dodging traffic.