The Confessions of Al Capone

The Confessions of Al Capone

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by Loren D. Estleman

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In 1944 Al Capone, the most notorious Mob boss in history, has already been released from prison. Though Capone is no longer the enormously powerful force who dominated Chicago’s underworld for years, he is still a thorn in the side of J. Edgar Hoover. The FBI chief knows that if he can somehow manage to get Capone to reveal details of crimes he and his


In 1944 Al Capone, the most notorious Mob boss in history, has already been released from prison. Though Capone is no longer the enormously powerful force who dominated Chicago’s underworld for years, he is still a thorn in the side of J. Edgar Hoover. The FBI chief knows that if he can somehow manage to get Capone to reveal details of crimes he and his Outfit committed, the Bureau has a good chance of nailing key members who now are active in the wartime black market.

FBI agent Peter Vasco is perfect for the job. He has an in—his father once drove a truck for the Outfit—and his pre-FBI education gives him even better cover. His orders: pose as the priest he wanted to be before he dropped out of seminary, get close to Capone, and get Hoover the information he demands.

Capone’s in Florida, suffering from advanced syphilis, and happy to add a priest to his inner circle. As Vasco and the mobster bond over card games, lunches, and even a trip to Wisconsin, Capone, sometimes lucid and sharp, other times rambling and vague, recounts stories of his criminal career. From his days as a bouncer in Brooklyn to the St. Valentine’s Day Massacre, Capone spills secrets that reveal in vivid detail the life of this monster who became the most iconic figure in twentieth-century crime.

Vasco is alternately fascinated and repelled by the things Capone reveals. Al Capone would stop at nothing to take what he wanted, but also fed the poor of Chicago; he rose to the top of Chicago on a tide of bootleg beer and booze, but took the time to ensure that innocent victims of Mob violence got proper medical care.

This is Al Capone as he’s never been seen before, a ruthless crime lord who trafficked in death and corruption…as well as a man of refined tastes who loved his family. A man whose life is waning, and perhaps, a man who is seeking absolution.

Editorial Reviews

Publishers Weekly
Edgar-finalist Estleman (Burning Midnight) presents a nuanced and compelling fictionalized portrait of the best-known gangster of them all, Al Capone. In 1944, J. Edgar Hoover pulls Peter Vasco off a desk job for a special undercover assignment. Capone is in Florida, dying of syphilis, and Hoover hopes the right person can get information from him that would enable the bureau to make cases against successors to his criminal throne. As Vasco’s father was acquainted with the mobster from a long-ago incident, the young investigator is tapped to pose as a priest and work his way into Capone’s inner circle to elicit what useful information he can. The book alternates between third-person description of Vasco’s efforts and a convincing first-person narration by Capone as he shares some of his secrets. Estleman captures his lead’s ambivalence at deceiving others for a greater good perfectly, and the directions the plot takes aren’t always foreseeable. Agent: Dominick Abel, Dominick Abel Literary Agency. (June)
From the Publisher

“This is a book that took courage as well as talent to write. Loren Estleman has managed a literary miracle, a story full of surprising discoveries and often deep emotion.” —Thomas Fleming, New York Times bestselling author

“Remarkable research, rich storytelling and a rapid, riveting pace make The Confessions of Al Capone one of this year's most stimulating and exciting reads. Hits with the force of a burst from a tommy gun.” —Ralph Peters, New York Times bestselling author of Cain at Gettysburg

Library Journal
In 1939, Al Capone was released from Alcatraz after serving a seven-and-a-half-year sentence for income tax evasion. Suffering from the effects of syphilis he had contracted as a young man, the former gang boss retired to a palatial beach house near Miami, where he lived with his wife and son until his death in 1947. Into this historical scenario, Estleman, the popular and award-winning author of 70 novels, weaves a gripping fictional tale of a young FBI agent on a perilous mission. Owing to his family connections with the Capone “outfit” and his training at a Catholic seminary, Peter Vasco is seen by FBI director J. Edgar Hoover as an ideal tool with which to infiltrate Capone’s household, masquerading as a priest, and collect information that can be used to investigate Capone’s family and associates. In addition to this difficult mission, Vasco faces the awkward duty of mending his strained relationship with his father, whose link to the Capone gang during Peter’s childhood years remains murky and unexplained, and his own unresolved feelings about his unfinished religious training. Estleman’s Capone is a complex and multifaceted figure: jovial family man, convivial host, sharp-dressed fashion plate, and pensive retiree contemplating his memories and mortality. Although mentally deteriorating, he is still, on his good days, a canny judge of character who is capable of ruthless retaliation.

Verdict A tense and thoughtful historical thriller, recommended for all fans of crime fiction and historical novels. [Previewed in Kristi Chadwick’s “Following the Digital Clues: Mystery Genre Spotlight,” LJ 4/15/13.—Ed.]—Bradley Scott, Corpus Christie, TX
(c) Copyright 2013. Library Journals LLC, a wholly owned subsidiary of Media Source, Inc. No redistribution permitted.

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Read an Excerpt




An invitation to the director’s office always meant termination. Even a man without faith could depend on that.

It was waiting for him on his desk, in a large brown interoffice envelope tied with red string, neatly typed in elite characters on the same undersize stationery the Director had used to congratulate the men who killed Dillinger:

Peter Vasco

Division Four

Records and Communications

Dear Mr. Vasco:

The Director would appreciate your presence at the SOG at 1400 hours this date.


Helen W. Gandy

Gandy was the Director’s executive assistant: “Hoover’s secretary” to the unindoctrinated. She’d sat outside his door since his appointment to the General Investigation Division in 1919, and had processed every decision he’d made from the start, including converting to the military timetable after Pearl Harbor. SOG stood for Seat of Government. In early days this had referred to headquarters’ location in the District, but more recently it had become shorthand for the Director’s own office, and by extension the Director himself.

To compare the Bureau to a beehive was a cliché, but clichés are nothing if not accurate. At the center was the queen—a career-destroying description if overheard, given the rumors that circulated among the Director’s enemies on the Hill. The field agents were the scouts swarming outside, while the drones inside worked around the clock to maintain the hive. Vasco was the drone of drones, assigned to proofread non-classified instructions to Special Agents in Charge and the odd innocuous press release for errors of spelling and grammar. The aptitude test he’d taken when he applied for employment had shown a high degree of stenographic ability; with no background in law or accountancy he’d hardly hoped for a field position, but it was dreary, tedious work, with the added inducement of a reprimand in his file if a single participle continued to dangle once it left his desk. The smallest blunder festered throughout the system and had to be cauterized at the source.

Evidently a proper noun had escaped capitalization or, worse, a live document had been swept into the wastebasket with the day’s litter and sent directly to the incinerator where obsolete secrets were interred in the ashes. Vasco wasn’t incompetent on the job, merely indifferent to it. That hadn’t always been the case, but after nearly a year shackled to the same tin desk in a room filled with them, his hopes for advancement had died—pounded flat by the incessant artillery barrage of booming drawers and typewriters thundering on metal stands. He suspected that on some subconscious level he’d realized that consistency and reliability counted against change rather than for it, and had sabotaged himself deliberately.

Shrink talk. Swallow two opiates with water and say three Hail Marys. The Director had no use for either, and these days neither did he.

Whatever the nature of the dereliction, it was beneath the attention of a man concerned with keeping Fifth Column spies out of the War Department; but the Director had been known to take interest in petty personnel matters. He’d fired a veteran inspector for reporting in from sixteen hours of surveillance with his shirttail hanging outside his vest. Vasco’s own supervisor had forgotten to wear the regulation fedora in a press photo and forfeited his chance to head up the Detroit office.

The morning dragged past on flat tires. He ate a sack lunch, an egg salad sandwich provided by ration stamps he’d been hoarding, but it might as well have been boiled pulp for all he tasted it. At quarter to two he walked up the aisle between rows of desks, a condemned man resigned to his fate. His colleagues discovered a sudden fascination with their little correction marks as he passed. They all knew about the envelope. For an organization dedicated to national security—it had practically coined the phrase—the Bureau was the whisperingest place outside the community rooms across America where mothers and daughters turned peach pits into weapons-grade cyanide.

Stepping off the elevator on the fifth floor, he followed a beige hallway carpeted in navy—Justice Department colors—and lined with diversions. Inside brushed-aluminum frames Hoover shook hands with presidents and movie stars, squinted through a tommy gun sight, and walked his cairn terrier, G-Boy, beside the Potomac. Arsenals bequeathed by various bandit gangs shared glass cases with heroic G-man movie posters, pieces of exploded hand grenades, a replica of the Justice building assembled from popsicle sticks, and bulletproof vests hemorrhaging steel wool out of vicious holes torn in the fabric. The Black Museum, senior agents called the display. A small library of books in shiny jackets arranged face out bore Hoover’s name as either the author or the contributor of a foreword. Ghostwritten, every one, but doubtless the galley proofs had passed across his desk and then those of Vasco’s superiors in Records and Communications, to eliminate heresies and stray commas. John Dillinger’s morgue session had a case to itself, including bits of federal lead dug from his corpse and the infamous shot of the bank robber’s storied twelve-inch erection skewing the line of the sheet covering him. The visitor searched in vain for the actual member preserved in a jar of alcohol. Another myth shattered: but at the Bureau there was no shortage of legends even in wartime. They issued forth like bombers from an assembly line and took flight immediately.

Despite all the sniping from inside and outside the hive, and perhaps partly because of it, Vasco’s admiration for the Director bordered on worship. (Patton’s men, it was said, smirked at the general’s jodhpurs and pearl-handled pistols, but would follow him into hell.) A twenty-four-year-old U.S. attorney with little experience, Hoover had taken charge of a government agency created for the sole purpose of political patronage, turned out the rascals by guile and force, and within a few years transformed it into the most efficient police department in the world. Vasco was fourteen when Hoover made international headlines by singlehandedly arresting Alvin Karpis, Public Enemy Number One, after Karpis had boasted publicly that he would kill Hoover for the slaying of his outlaw friends the Barkers in Florida. A newspaper photo of the Director leading the murderer-kidnapper in manacles into the Federal Building in St. Paul had gone up on the wall in Vasco’s bedroom between Jesus and the Pope.

He hesitated before the door to the reception room. He’d never met the man who’d hired him, had seen him in person only from a distance, presenting badges to graduates of the training course during the turning-out ceremony. This was his first time on the executive floor. Opening the door was like taking the Eucharist; there was no going back. He wiped his palm on his trousers and twisted the knob.

Miss Gandy—as it was with Hoover, there was no spouse in her life, but dirty-minded rumors withered in the monastic atmosphere that hung over this Vatican—sat behind an ordinary desk in command of extraordinary equipment: intercom, black bulbous telephone with rows of buttons lit up like a movie marquee, a Dictaphone player, an Electromatic Typewriter the size of a radio-phonograph on a stout table placed perpendicular to the desk. She was chugging away at the last. At her back, a larger table supported a similar machine linked to a Teletype, waiting to receive and decode ciphers from the White House and Pentagon. Vasco recognized this arrangement from the March of Time, dozens of Siamese-twin machines chuckling in a big room in an undisclosed location, but hadn’t thought he’d ever find himself in the presence of one. It was an imposing sight, and incongruous in view of the unprepossessing figure in charge.

If Helen Gandy had ever been photographed, Vasco had missed the result. She took no visible role in official functions. Yet another legend insisted that she had a private apartment in the building and hadn’t ventured outside since the Coolidge Administration, preferring to serve her master day and night in the holy war against criminal rats, the Nazi-American Bund, and Eleanor Roosevelt. In the dense mist of such speculation, Vasco forgave himself the mental picture of a sour-faced spinster in black bombazine, lace-ruffled to the throat, spectacles constricting the blue veins in her nose. Any one of the sisters of St. Francis could have served as the model.

What he saw, when she swiveled to face him, was a pleasant-faced redhead in her midforties with freckles on her cheeks, wearing a pale green blazer lightly padded in the shoulders, jet buttons in her ears, and a necklace of the same polished coal stones around her neck. She smiled at him with slightly crooked teeth.

“Mr. Vasco? Most punctual. I’m Helen Gandy. The Director asked me to show you in the moment you arrived.”

“Thank you.” Traumatic thought: What if he’d been thirty seconds late? Could a man be fired twice?

She rose, smoothed her skirt, and led him to a paneled door with a knob engraved with the FBI seal. He caught himself glancing at bare muscular calves—nylon was for making parachutes—tendons stretched by platform heels, and averted his eyes in a rush of facial heat. It was like lusting after his den mother. He felt like scourging himself.

Here was Xanadu, the stately dome: if not of pleasure, then at least of imperial splendor. The walls were paneled and polished, and plush navy carpeting cloaked the floor with the ubiquitous seal embroidered in gold in the center and mounted in relief on the back wall. The room was vast, but it was in proportion to the desk, which ought to have been called something else because it did not belong in the same category as Vasco’s tin station. A massy gold eagle stood sentinel with wings half-spread astride matching ink receptacles on the near edge. Gold-fringed flags of the United States and the District of Columbia flanked the desk in brass stands rubbed to a high yellow shine. Images of the place Vasco had seen in dim picture palaces before the main feature didn’t do it justice. A brief glimpse of the Seat of Government in person seemed sufficient to snuff out any felonious conspiracy at the start.

“Not here, Mr. Vasco. The Director wishes to see you in his office.”

He had stopped before the great desk, and in his reverie had failed to note that Miss Gandy had continued past it to another paneled door half-hidden behind a swag of blue-and-beige bunting. Belatedly he realized that the fabulous room was just for show, reserved for press conferences and photo sessions with famous faces: a deception, but more in the line of a magician’s trick cabinet than a movie set. The fifth floor was a place of sliding panels, secret passageways, and strangers’ eyes peering out through holes cut in paintings. Far from being disillusioned, he was charmed by the sorcery.

Beyond the last door the magic evaporated.

Vasco disliked square rooms. They reminded him of wooden packing crates—intriguing at first glance, but which once the straw was removed contained homely hymnals, Bible stories Bowdlerized for the consumption of children, blobby pewter candlesticks, and plaster saints with bored expressions that passed for piety. Nothing wondrous ever came from a crate. This one was twelve-by-twelve and might have been used by an insurance adjuster. Banks of olive-green filing cabinets stood like gym lockers against the side walls and a community of grubby file folders in stacks made city blocks on a plain wooden table. A green-shaded banker’s lamp on the table and a single overhead globe created an island of light in an ocean of murk. National Geographic maps of the European and Pacific theaters of war were pinned to a wall beneath portraits of Washington, Lincoln, President Roosevelt, and for some reason Davy Crockett.

A small man with a big head sat in an upholstered chair behind the table, engrossed in the contents of a folder flayed open before him. He was built like a bantamweight boxer running to fat, with coarse hair brushed straight back from a bulging forehead and eyes that stuck out like white rubber door bumpers beneath heavy black brows. His nose was blunt, his cheeks jowly; “bulldog” was the popular description, “porcine” common among detractors. Vasco, whose own face had been compared to a rodent’s, was less judgmental. He thought the Director heroically ugly and appropriately intimidating, like a boar in the forest. J. Edgar Hoover should look like nothing else.

“Peter Vasco, sir.”

“Thank you, Miss Gandy.”

She drew the door shut as she retired, sealing them in silence.

For most of a minute—if minutes were generations—Hoover continued to study the sheets before him, reading one page to the bottom, turning it over, and starting on the next as if he were alone. Vasco remained standing. He tried not to look at the carpeted platform that raised the table and its owner six inches from the floor. He’d heard that the stool the Director stood on during the turning-out ceremony was a litmus test for new special agents: one glance at his feet and the man went away empty-handed and out of a job. The effort of not looking down made his eyes want to water, and he found no comfort in the realization that the folder on the table contained his own personnel file.

Suddenly it smacked shut. He felt the full heat of Hoover’s hard-boiled-egg gaze, white all around the irises.

“Sit down, please.”

Four chairs covered in soft leather faced the table. The one he chose was less comfortable than it looked, the legs too short by inches so that he felt as if he were sitting in a tub. From that position the Director towered above him on his platform.

The one-sided staring contest continued a few more seconds. Vasco scratched an eyebrow, giving himself the chance to blink. The hot gaze shifted to a pudgy hand brushing the folder.

“You’ve been with the Bureau ten months and have yet to take a sick day. Why?”

He blinked again, openly. “I haven’t been sick, sir.”

“I hope that’s true. Some people believe reporting to work ill is evidence of dedication, paying no mind to the half-dozen people who are forced to stay home the next week because of all the plague germs they left lying about. Are you under the impression you’re indispensable?”

“No, sir.”

“Because there is only one person this organization cannot possibly do without.”

Inspiration seized him. “Miss Gandy.”

Hoover stared. Vasco was sure he’d outsmarted himself. The obvious answer was not always the right one, but it was politic.

“We begin well,” the Director said then, and Vasco resumed breathing. “Most people would say it’s myself, and hope to curry favor. Nothing is so insincere as flattery, especially when it’s addressed to a superior.”

He felt a little less ill at ease. Hoover’s speech was rapid-fire, a verbal strafing delivered in a nasal tone Vasco associated with radio announcers heard on tinny receivers. The words seemed to come a thousand to the minute, like rounds from the Model 1928 Thompson (familiarity with the Manual of Arms was required of all employees, in the field and at home). A man wanted to duck rather than respond; but he had remembered the Director stating the invaluability of Helen Gandy’s services for the record when he’d added “executive” to her title, and the memory had surfaced during the onslaught. He still couldn’t guess the reason he’d been summoned, but he’d begun to believe that it wasn’t his dismissal.

“You’re Sicilian?”

“Calabrese, sir. Irish on my mother’s side.” That was safe enough. A man couldn’t help his ancestry. “I was born in Chicago.” He couldn’t remember if a birth certificate had been necessary for employment. Almost everything else had.

Hoover twisted around in his chair. He seemed to be searching for Calabria on the war map. It was peppered with red-white-and-blue flag pins. Mussolini had been captured once, then freed by the German Army; Vasco hoped he hadn’t unpacked.

“You’re still a practicing Catholic?” Hoover turned back, adjusting the padding in one shoulder. His double-breasted suits were tailored to correct deficiencies.

“Practicing? No, sir.”

“Question of faith?”

“I have no questions.”

“Atheist?” The heavy brows drew together.

“No, sir. I just stopped asking.”

“Is that why you quit the seminary?”

“I failed. Many are called…”

“No judgments, understand. I have Roman Catholics in the field. Good men. None of them studied for the priesthood, which is why I asked to see you. One of the reasons. How much do you remember from your training?”

Only every novena, the names of all the saints, where the good vintage was kept so it wouldn’t get mixed up with the swill they served for the sacrament. He practically farted in Latin. “A fair amount.”

“We’ll arrange a refresher course.”

“A refresher course?”

“Are you still in contact with your father?”

He sat a little straighter, and he had not been slouching.

“I got a card last Christmas.”

“No scenes in public, I hope.”

“Our differences are private. With all due respect,” he added. So it was possible to forget who he was talking to when that subject came up.

Hoover smiled. He had excellent teeth; Vasco suspected extensive orthodontia in early adulthood. They gleamed like new appliances against the Director’s swarthy skin.

“There’s no need for secrecy. Did you think, just because you applied for a low-clearance position, your background wouldn’t be checked? Paul Anthony Vasco had a wife and a child to feed and clothe, a roof to provide. That was difficult enough for an unskilled laborer during the Depression, and harder still for a recent immigrant in a city crawling with them. He drove a beer truck when beer was illegal and performed odd jobs for the Capone organization. I’ve been called a puritan and a martinet, but I’d be worse than that if I held a man’s bad choices against him after all this time. Worse yet if I visited the sins of the father upon the son. You wouldn’t be working here if I did.”

“We haven’t spoken since before I joined the seminary. He thought the decision was a joke.”

“Your dropping out would only support that opinion, in his eyes. I understand.”

“No, sir, I’m afraid you don’t.”

Hoover’s smile was a thing of the past—dead, petrified, and buried in dust. But Vasco was committed and stumbled on.

“My father liked his work. He had a decent job driving a cab in Cicero, but one day a thug hailed him, threw a pistol into the backseat with some cash, and told him to step on it. He did, just as a policeman came running up with his gun out and ordered the thug to throw up his hands. That night the same thug came to our apartment, took back his pistol, and gave my father a hundred-dollar bill from a roll he carried in his pocket. He also gave him a business card and said to look him up if he ever got tired of pushing a hack. My father quit the company the next day.”

“What was on the card?” The Director seemed to have forgotten his pique.

“Al Brown, Antique Dealer. I’m sure I don’t have to tell you who Al Brown was, sir.”

“Al Capone. That must have been early in his career. He dropped the alias when he got big.”

“The gun had been used to murder a man named Howard,” Vasco said. “My father said the barrel was still hot. I don’t want to know anything about those odd jobs.”

“No one would blame you. Nothing is worse than betrayal. However.” Hoover dragged another folder off a nearby heap. The file was much thicker than the one that contained Peter Vasco’s life and secured with a piece of dirty cord. He slipped the knot and spread it open. His fingers were pink and immaculate, like a baby’s.

“This wind wasn’t so ill it failed to blow some good. Your flirtation with the spiritual life wasn’t enough to take you out of Division Four. If it weren’t for your father’s indiscretions I wouldn’t have been able to use you at all.” He drew out a newspaper clipping and placed it on Vasco’s side of the table.

Vasco had to climb out of his chair to see it. It was brown and brittle and had a five-year-old date scribbled in red ink in one of the margins. He saw a picture he’d seen before, of a broad flat face photographed close up under a white Borsalino hat with the brim turned up rakishly on one side, and a headline:



Copyright © 2013 by Loren D. Estleman

Meet the Author

LOREN D. ESTLEMAN has written seventy books, including The Confessions of Al Capone, Ragtime Cowboys and You Know Who Killed Me. Winner of four Shamus Awards, five Spur Awards and three Western Heritage Awards, he lives in Central Michigan.

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The Confessions of Al Capone 3.8 out of 5 based on 0 ratings. 4 reviews.
Anonymous More than 1 year ago
Anonymous More than 1 year ago
Who is this al capone and who is scareface who said say hello to my little friend.
Anonymous More than 1 year ago
tedfeit0 More than 1 year ago
The question is: Is this book a novel in search of history, or history in search of a novel? Certainly, it is a well-researched effort, recalling the career of Al Capone, one of the most notorious crime bosses in the history of the United States. His career is traced through a series of meetings with Peter Vasco, posing as a Catholic priest, who is placed in a position of intimacy with Capone after his release from prison for tax evasion by J. Edgar Hoover in an effort to obtain evidence to go after his associates in Chicago. Characterizations are the key to the novel, portraits that are incisive and penetrating. J. Edgar Hoover comes up short as a person. Vasco, who is merely a clerk in the FBI, suddenly becomes a special agent and blossoms as an undercover agent, more than unlikely in real life. His putative father, Paul, is an amusing personality. Other characters are merely fill-ins. It is a gripping tale, well-written. The author apparently set out to capture the essence of Al Capone, and it seems he was successful. Whether he did so for the others who populate the pages is questionable. However, the confessions, after all, are those of Al Capone, and as such are vital and readable. Highly recommended.