As the months dragged on, Rudensky became ever more fond of Capone, outbursts of temper and all.
It wasn’t hero worship but something else [Rudensky wrote in The Gonif]. I could understand him being hateful or vitriolic but he wasn’t. Oh, he’d storm over the inefficiency of his latest attorneys. He’d confide to me, “They’re overpaid dumb bastards who couldn’t spring a pickpocket. They should have had me out of here three weeks ago.”
But his flare-ups . . . died quickly. He’d spend hours mulling over letters from his family or reading papers and sports magazines. Despite his sinister reputation, Capone was a family man and religious too. He showed me his son’s picture and asked, “How in hell can a fat dago like me have a son that good lookin?”
When not brooding or ranting, Capone gave way to irrational episodes of high spirits. He and Rudensky often listened with earphones to the hit comedy series on radio, Amos ‘n’ Andy, and after hearing a particularly amusing routine they started laughing uncontrollably. Ripping his earphones off, Al shouted, “I’ve just thought of the funniest damn thing you’ll ever hear. I’m supposed to be the big shot, and I’ve wound up in the shoe shop. You’re supposed to be a safe cracker, and now you write goddamn editorials. What kind of a screwed up, lousy world is this?” After they speculated on what would happen if they pursued these trades on the outside, Rudensky recalled, “I fell into Al’s arms and we held each other like two kids celebrating First Communion. I whispered in his ear, ‘Al, it’s not so much that I can read and write, it’s just that you know so damn much about shoes!’ ”
The two of them fell to the floor; their raucous laughter brought a guard running to the cell, demanding to know what they thought they were doing. Capone bellowed in reply: “Just a couple of sweethearts meeting after the prom, you dumb bastard.” At moments like these, Rudensky, against his better judgment, fell helplessly under Capone’s spell. He was, after all, the great “Scarface.” Rudensky brought up the St. Valentine’s Day Massacre, just to get a reaction, but Capone only laughed at the mention of the most famous slaying in the history of gangland. “Those silly Irish bastards,” he wailed. “They have more guts than sense. If we’d only hooked up, I could have been president.”
That was the Capone bravado—endearing and outrageous. Throughout all his months in the hot, claustrophobic Atlanta Penitentiary, he remained a great hoper and believer in himself, in the future, and in the one twist of fate that would spring him from jail. A deus ex machina in a gray flannel suit. Fate appeared to cooperate with Capone when the U.S. Supreme Court amended some of the laws applying to his case. The revision was purely technical, but Capone, desperate for any source of hope, eagerly clutched at it. At the time of his trial, federal statutes specified that prosecution for tax violations could include offenses no older than three years, except for schemes “defrauding or attempting to defraud” the government, in which case the limit extended to six years. Capone’s indictments went back as far as 1925, and the most recent offense occurred in 1927—four years earlier. Then, in the spring of 1932, the Supreme Court ruled that avoiding federal income tax was actually not “fraud” after all, and the three-year limit applied. By this reckoning, Capone’s tax violations had occurred outside the new time frame. Once he grasped the significance of the ruling in his own case, Capone decided to jettison Ahern and Fink, who had proved so inept in defending him, and from his cell in Atlanta he ordered his family to hire two new lawyers in Washington. Tax specialists, they filed a writ of habeas corpus before Federal Judge E. Marvin Underwood of Atlanta, Georgia.
Freedom seemed tantalizingly closer when Capone appeared in court as part of the legal initiative. He gained his first headlines in months, but they told a pathetic tale. “AL CAPONE MAKES NEW LIBERTY PLEA,” declared a representative headline in the New York Times of September 22, 1933. “HE APPEARS IN HANDCUFFS. Gangster, Thinner and Subdued, Spends Five Minutes in Court while Hearing is Set on Writ.” In addition to the handcuffs, he was manacled. He had lost over forty pounds during his stay in prison and now weighed 215 pounds. Capone listened to his lawyers make their arguments, and within three hours of his court appearance, he returned to his cell, where he had to wait until December for the judge’s ruling. The last thing this judge wanted was to be known as the man who set Al Capone free on a technicality, even though the government had put him in jail on a series of technicalities. So Judge Underwood peered deeply into the wording of the relevant statute, which stated in part, “The time during which the person committing the offense is absent from the district wherein the same was committed shall not be taken as any part of the time limited by law.” On that basis, he ruled that the months and years Capone had spent away from Chicago—in Florida, in Philadelphia—could be deducted from the limit, and thus Capone was still fully accountable for his failure to pay taxes. With that, Judge Underwood dismissed Capone’s plea for freedom.
• • •
As Al Capone encountered one legal frustration after another, the Chicago Police Department and U.S. government agents made steady progress against the Capone organization. One brother, Albert, was arrested in connection with the bombing of the home of Cicero’s mayor; he was the youngest of the Capone boys, and prior to the arrest he had no police record, but after he was freed, he was constantly watched. Soon after, another brother, John, was ordered to testify before a federal grand jury investigating the liquor rackets. Meanwhile, President Hoover, in the waning days of his administration, rewarded George E. Q. Johnson, the U.S. attorney who had prosecuted Al Capone, with an appointment as a federal judge, and his assistant, Dwight Green, received a promotion. Later, Green was given to gloating over Capone as convict. “He behaves so well in Atlanta that the other inmates are beginning to think he is a milksop,” he announced. “He has been trying unsuccessfully to get a place on the prison baseball team. He is a model prisoner, and obeys every order the second it is given. His face is bronzed and his figure has become trim and lost its paunchiness. He has now become a valuable worker in the prison shoe factory.” As the prosecutors discovered, jousting with Capone was an excellent career move: Johnson later devoted himself to a lucrative private law practice, and Green went on to win election as governor of Illinois.
Their ascendance did not mean the end of lawlessness and violence in Chicago. Quite the opposite. Unknown to them all, Frankie La Porte continued to dominate the rackets from his base in Chicago Heights, and his nearly invisible supervision of the syndicate helped make it possible for other members of the Capone organization to pick up where they had left off before they went to jail. One by one their sentences ran out, and the men, having paid their debt to society, regained their liberty. In February 1934, Ralph Capone’s lawyers paid a $10,000 fine, and he finally left the McNeil Island Penitentiary, where he had been confined for a little more than two years. He was able to leave early thanks to time off for good behavior. He had passed the time cooking (although prisoners complained he used too much spice), playing baseball (working his way up to starting first baseman for the prison team), and learning a little Spanish. “Capone became a model prisoner after he learned that no one in this prison gets anything unless he earns it,” said Warden Archer on the occasion of Ralph’s release. “At first he complained about the hard work and his lack of privileges. When he understood the situation, he turned to and worked.” Ralph’s wife, Valma, was there to greet him when he reached the mainland, and the two of them departed in a limousine. The next morning, the newspapers taunted him, claiming Ralph Capone would be out of work in post-Prohibition American society, but the newspapers were wrong; his old job as a racketeer was waiting for him. Although he had lost nearly thirty pounds in jail and had grown a thin mustache, Ralph was basically unchanged; he still liked the horses and still carried the nickname “Bottles,” and he slipped quickly and comfortably back into his old life. Unlike his younger brother, Ralph was blessed with an easygoing temperament; his prison sentence instantly became one more unpleasant exper
ience he put behind him.
Frank Nitti also returned to freedom. In January 1931, he had begun serving his sentence for income tax evasion at Leavenworth. Several months later, his wife wrote to the parole board to plead for her husband’s early release, her letter a compilation of half-truths and wishful thinking. “Frank and I have been married for three years and this is the first time he has been away from me,” she told them. Implying that he would have nothing further to do with the Capone organization, she went on to explain, “We both agreed that to return to Chicago, where he is known and everyone aware that he has been in the penitentiary would be the wrong thing to do. He has been offered a job with the Forest Dairy of Kansas City, Mo. at a wage sufficient to maintain us in comfort. As soon as he is released I will join him in Kansas City, make him a home, and keep him on the straight and narrow path in the future.” Her plea and promise to move to Kansas City failed to win her husband his early freedom, however, and Nitti served his full sentence, though he did receive time off for good behavior. After little more than a year in jail, he returned to Chicago (so much for the job in a Kansas City dairy “on the straight and narrow path”) and resumed his place in the Capone organization. Although he earned the nickname “The Enforcer,” as if he were the Capones’ hit man, in reality Frank Nitti was too quiet and nervous to engage in violence. He enforced his will not with a machine gun but with a telephone and a pen, and as the Capones languished in jail, he served as custodian of the organization.
Jack Guzik—Orthodox Jew, pimp, and accountant to the syndicate—was the next to go free. Having done his time at both Leavenworth and Lewisburg, Pennsylvania, he received his discharge on December 15, 1935; he was another model prisoner, presumably reformed, who immediately resumed his former duties. A year later, Murray Humphreys, the youngest member of the Capone syndicate to serve time for income tax evasion, graduated from Leavenworth and returned to his rightful place in the rackets.
Even though they were at liberty, it was a different world for the old gang now. They were ex-cons, for one thing, and the prison experience had marked them, made them more secretive and fearful, and it had branded them as outlaws, inflicting psychic scars on both them and their families. They now bore a lifelong stigma. It was harder for ex-cons to buy judges and politicians, and the glamour of la mala vita was gone, a casualty of the Depression economy and a sea change in society’s values. The racketeers still drove their big sixteen-cylinder Cadillacs, and their wives still wore furs and diamonds, but there was less ostentation now—and less money. Their customers had less to spend on gambling and brothels, and once Prohibition was repealed in 1933, the syndicate’s largest source of income dried up.
Prohibition had been a mixed blessing in the end, for bootlegging had been a far more vicious and volatile business than any of them had expected, and far more visible. Given the nature of their business, they were always more comfortable on the margins of society, but bootlegging had dragged them center stage. As Capone himself had noted, the process of manufacturing, importing, and serving alcohol had brought them into contact with virtually every level of society, from the spacious penthouses along Lake Shore Drive to the crowded shacks on the South Side, but that heady visibility had, in the long run, proved to be a tremendous liability, exposing them to unprecedented legal scrutiny. It was as if Prohibition had been a giant trap set by the federal government to ensnare the racketeers, and they had all taken the bait and suffered the consequences. Had they never entered the illicit liquor trade, they might well have escaped notoriety and jail. Frank Capone, the handsomest, the most daring of all the brothers, might still be alive. For all these reasons, then, many racketeers were actually relieved by the prospect of repeal. Those who wished to remain in the liquor trade simply went legitimate, while the others returned to their core businesses: gambling and vice. Furthermore, the rise of labor unions offered the syndicate new worlds to conquer. All in all, the rest of the 1930s held promise for those racketeers who knew where and how to take their chances.
• • •
As his friends and brothers flourished on the outside, Al Capone remained in the Atlanta Pententiary. Cobbling shoes. Brooding on the failures of his lawyers. Out of touch. Slowly losing his mind. Without hope of imminent legal rescue, his second year in Atlanta proved to be even more depressing and difficult to bear than the first had been. Speaking from experience, Rudensky warned Capone that he was entering the most trying period of all; if he could get through it, he would come out OK. Capone responded by seeking refuge in grandiose fantasies. He constantly muttered about big people, well-connected lawyers and politicians, who would free him from jail any day now. There was a man in Washington, or so he said, to whom he paid $2,000 for just that reason. Often as not, he would wind up blubbering and lay his head on his cell mate’s shoulder and murmur, “Rusty, where the hell are all the guys you expect so much from?”
The poisonous combination of Capone’s increasing frustration and decreasing mental abilities led to a spate of disciplinary incidents during 1933. The most serious concerned an apparent plot to escape. A guard discovered eight sheets fastened to Capone’s bunk, some of them tied together; apparently convict number 40886 planned to lower himself from a window via a bedsheet ladder. It was a peculiar violation, more indicative of Capone’s disordered mental state than his cunning. In all, the incidents numbered about half a dozen, and after Capone received his reprimands, they were filed away and forgotten. But far more public charges of Capone’s receiving special favors surfaced early the following year, and these allegations, which were serious enough to warrant an FBI investigation, proved embarrassing both to Warden Aderhold and the Federal Bureau of Prisons, and they would have drastic consequences for Capone himself.
Many of the stories originated with other prisoners, snitches motivated more by jealousy than a desire for justice. Fearing for their lives—so they said—they hid behind pseudonyms as they claimed Capone had devised a system to bring money into the Atlanta Penitentiary, which he used to bribe guards and win preferential treatment. It is possible that Capone himself unwittingly started some of the rumors with his constant, delusional claims that he had “fixed” anyone who had power over him. Although the FBI’s investigation team found no substantiation for the stories, they entered the record and, even though unproved, cast a long shadow.
In the midst of these investigations, a veritable compendium of Capone’s special privileges came to light in the form of a mysterious, anonymous manuscript entitled “The Biography of Al Capone’s Life in the Atlanta Penitentiary.” The FBI looked into that, too, and the report of the investigating agent, E. E. Conroy, suggests the yarn’s smarmy tone: “There is an allegation to the effect that Capone would knock a tennis ball over the prison wall while playing tennis, and immediately afterward a different tennis ball would be returned over the wall from the outside. There is a suggestion that the substituted tennis ball contained narcotics.” Another scene depicted Capone receiving drugs contained in a tea bag concealed in the underwear of a visiting relative, and still other passages detailed at wearying length Capone’s attempts to obtain extra food and offer thousand-dollar bribes to incredulous guards. With its plethora of detail and malevolent air, the manuscript, nearly 250 pages long, had the earmarks of an inside job. The writer, who refused to come forth and identify himself, possessed enough knowledge of the prison’s day-to-day operations, as well as access to Capone’s records, to concoct a plausible scenario.
However, the FBI found the truth to be altogether different. As for the drugs concealed in tennis balls, “My knowledge of the prison and surrounding terrain leads me to believe that this allegation is ridiculous in the extreme,” agent Conroy concluded. Subsequent FBI inquiries turned up convincing evidence that Capone, rather than bribing others with fistfuls of cash, was actually the victim of extortion attempts made by other prisoners, who assumed he was wealthy and afraid and thus would yield to their demands. The threats Capone received, according t
o one report, included “death and bodily harm while at Atlanta Federal Penitentiary.”
Despite all these findings to the contrary, the suspicion persisted that Capone was somehow using his influence to obtain special privileges, as he had in the Cook County Jail. The rumors concerning his treatment reached a crescendo in the U.S. House of Representatives, where lawmakers heard allegations based on newspaper articles written by an ex-convict named Lee Molnar, who claimed that Capone had bribed his way into a life of well-fed ease in the Atlanta Penitentiary. Warden Aderhold denied all of Molnar’s charges, the most inflammatory (and far-fetched) being that Capone continued to wear his silk underwear, custom shoes, and tailor-made suits behind bars. No, said Aderhold, Capone wore only regulation underwear, suits, and shoes manufactured in the prison’s shop.
Oblivious to the public controversy surrounding him, Capone remained locked in the tight little world of the penitentiary, becoming ever more dependent on his level-headed cell mate Red Rudensky for emotional support. With a little help from “Rusty” he was learning to tolerate life behind bars, and as long as they were together Capone figured he could last until that bright day in 1939 when he was scheduled to be freed. Rudensky’s fund of convict lore gave the Atlanta Federal Penitentiary a human face, and Al, in turn, promised to take care of his buddy when they got out. Despite his announced determination to go straight, the former safe cracker found himself seriously tempted by the prospect of living the sumptuous life as a member of Capone’s inner circle. Their plans were all fantasy, of course. Had Capone possessed the mental acuity to read the signals, he would have realized that far worse awaited him in prison.
On May 27, 1934, the new attorney general of the United States, Homer S. Cummings, visited the Atlanta Penitentiary; this was the AG’s first visit to a federal prison, and although the occasion had no announced purpose, he did make it a point to observe its most celebrated inmate, Al Capone, and to investigate the rumors of preferential treatment. Cummings caught sight of Capone walking from his cell to the dining area. Chewing tobacco and slouching, convict number 40886 looked nothing like a fearless gangster. It seemed he was not receiving special favors, but of course one could never tell from mere appearances, and Cummings remained suspicious. As it happened, the AG was just then bursting with plans for a new addition to the federal penitentiary system: a restored military garrison designed to house irredeemable prisoners. Located in San Francisco Bay, the maximum security facility had become Cummings’s pet project. It was called Alcatraz.
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