IN A CLASSIC SCENE in Brian De Palma’s The Untouchables (1987), Robert De Niro’s Al Capone weeps to an aria from Pagliacci, and is interrupted by his main henchman, Frank Nitti, to inform him that an antagonist in the police has been executed. His face relaxes momentarily as he digests the news, then swells again toward euphoria. This counterpoint of refinement and violence seems essential to depicting Capone, in a way that it isn’t for other gangsters like, say, Bugsy Siegel or Dutch Schultz. In an earlier scene, after charming a roundtable of dinner guests with sharp one-liners and wisdom about teamwork, a tuxedoed Capone bashes one of the diners’ heads with a baseball bat until the man’s brains and blood spread over the rich white tablecloth. As his latest biographer, Deidre Bair, says, “He was so wildly charming, so blatantly outsized in everything he did, and so fully in the public eye that it was hard to believe such a good fellow and one so highly entertaining, he of the pithy quotation and catchy phrase, could be all that bad.”
And as bad as he demonstrably was, Capone tilted the axis of Prohibition-era high society as much as he did that of organized crime. No other gangster’s name — Siegel, Schultz, Luciano, Lanksy — summons as much cultural heft as Capone’s, his only possible rival being the fictional Corleone. Indeed, Capone seems as much a creature of the imagination as of history, given the innumerable and divergent interpretations in film, TV, books, and oral accounts since the 1930s. His nickname, Scarface, was borrowed for the title of a major 1932 movie with Paul Muni as a young Chicago hoodlum on the rise; and again in 1983 for another De Palma classic, whose main character Tony Montana’s flair and cold-bloodedness echoes that of the original Scarface. Based on Treasury agent Elliot Ness’s self-aggrandizing, posthumous 1957 memoir, The Untouchables, while grossly exaggerating Ness’s role, portrayed the effort to bring Capone to justice as a conventional Good versus Evil battle. By contrast, the hit TV show Boardwalk Empire sometimes goes too far in the direction of casting him in a noble light. For example, in an important scene in season one, a young Al beats Arthur Finnegan, a low-level enforcer from a rival Irish gang, half to death because Finnegan had earlier slugged a Capone colleague from behind. In truth, we learn from Bair, Capone was provoked when Finnegan “made insulting remarks about Irish girls who married Italians.” (Capone, the son of Italian migrants, married blue-eyed Mary “Mae” Coughlin before his 21st birthday.) To help get past the myth and closer to the man, Bair has given us Al Capone: His Life, Legacy, and Legend.
Writing Capone’s life is challenging, given that there was little he or those close to him left behind that could provide insights into what drove him. His public deeds, nevertheless, provide some answers about how such a man obtains, maintains, and then loses power. The obvious starting point is his will to violence. The beating of Finnegan — which really did happen — was an impressive demonstration of this. It was also certain to invite lethal retaliation, prompting young Al’s move from Brooklyn to Chicago, where under the tutelage of Johnny Torrio, he steered the criminal Chicago Outfit’s dramatic expansion into gambling, prostitution, and bootlegging; and where, in a short six-year reign (after Torrio retired), he became the world’s most famous gangster. Through it all, he remained a family man, if a regularly unfaithful one, with Mae and their son, Al Jr., a central part of his life until his death in 1947.
As brutal as he was, Capone recognized the importance of connecting with the public, which he did through generous handouts and philanthropy; the kind of lavish parties depicted in The Untouchables; and charming the press. Perhaps more important to his stature, though, was the perception of his being above the law. As prosecutors failed to prove charges against him and judges were forced to set him free, Capone’s reputation grew in the direction of folklore. After one such case, in 1926, Bair writes, “The first order of business for the undisputed victor was to receive the homage that would solidify his rightful place as the supreme head of Chicago’s underworld.” He ran the gangster’s equivalent of the deep state, with so many ties to corrupt Chicago politics (including the infamous mayor Big Bill Thompson, and half of Chicago’s police on his payroll) that any attempt to bring him to justice would be tainted from the start. Not to mention the manpower he threatened to turn loose on the city if anyone tried to put him out of business.
Above all, however, was the lucky timing of the Great Experiment, a.k.a. Prohibition. Al’s early life in Brooklyn suggests that he was inclined toward violence and law breaking (as a teenager, for example, he started a mini extortion/protection racket targeting shoeshine boys on Columbia Street), and it’s fair to speculate that if the Great Experiment hadn’t been applied during his adult years, he would have found another criminal calling. “In those days,” Bair writes, “Italians not only started out at the bottom; they stayed there”; crime provided a way to break the vicious cycle of under-privilege. What Prohibition did was raise the social status of such men, as crime became not just tolerated but a necessity to guard “our way of life.” As Dr. Kate Drowne, a professor and author of the book Spirits of Defiance: National Prohibition and Jazz Age Literature, 1920–1933, put it, “With the advent of Prohibition in 1920, America suddenly became a nation of lawbreakers, many of whom had serious doubts about the wisdom and efficiency of the government.”
There is, therefore, a moral dimension to Capone’s appeal. He represented the counterpoint to a failed 13-year policy, which was the consummation of a prudish coalition of Protestant revivalists, the Anti-Saloon League, and some in the Progressive Movement who believed government had a positive role to play in bettering human behavior. The 18th Amendment, which came into effect in 1920, was the first constitutional reform to restrict personal liberty rather than that of the state. Unsurprisingly, the mainstream didn’t take this well. The author Richard Connell began an April 1920 Vanity Fair piece with these beautiful findings:
A terrible discovery has lately been made with regard to New York society. We who inhabited it had a way of thinking that it was the ladies, the wits, the spirit of badinage that made our dinners and evening parties so agreeable, so desirable, so much worth while struggling to attend. But along comes January 16th and opens our eyes to the true facts of the case. It was Alcohol that was really king; it was champagne we mistook for wit, and cocktails that put in our minds the idea that men were brave and women beautiful.
Bair would have done well to include more of this context upfront, to highlight how disruptive the Volstead Act was. The crisis it provoked turned booze into an elite currency; dealing in it came with a new vocabulary. For example, according to Connell, an “RSVP” on the left side of an invitation card had the standard meaning, but if on the right it meant “Real Scotch Voluminously Provided.”
Also writing in Vanity Fair, in 1926, Sherwood Anderson argued that Prohibition was confirmation of a “State more and more losing its grip on men’s imaginations, the State, as a controlling factor in lives, becoming constantly more and more ineffective.”  The rise of the authority and legitimacy of an Al Capone mirrored the decline of a government that had turned obsolete values into law. In some ways, he was a healthy thing to happen to the United States; the 1920s could turn to him and find a moral argument against the puritanical forces that had carried the day. Which isn’t to say that Al Capone wasn’t as mean as they come — just that the mainstream was willing, for a while, to abide his transgressions if it meant keeping everyone lubricated.
Although speakeasies blurred the line between high and low society, old money and new, that line still existed. Bair contends,
Al Capone was new (and openly dirty) money, and he could use it to try to wedge his way into their [the elitist residents of Lake Shore Drive] environment by acting, dressing, and living in a manner he thought mirrored theirs, but he could never be a part of it. They might have enjoyed toying with what was sometimes called “gangster chic” to describe the middle class’s attraction to the underside of society that began during Prohibition and particularly the larger-than-life figures who inhabited the criminal world. However, there was an unbridgeable difference between the residents of Lake Shore Drive and Al Capone of Prairie Avenue: when they tired of their pet crooks, they always had the option of dropping them and going home; there was never any chance that they would let Al Capone go with them.
While Bair spends much time — too much of it — trying to clear the clutter of Capone myth, she is at her strongest when she gets out of the biographical weeds and gives us a feel of the era. Her most articulate associations of Capone and his times come in the final chapter, and one wishes they’d come earlier, to give better definition to the culture that Capone and the Outfit dominated for a time.
So, how did a corrupted system and society ultimately bring Capone down? It seems that the lawmen were determined and prepared, to quote Robert Bolt’s Sir Thomas More in A Man for All Seasons, “to cut a great road right through the law to get after the Devil.” A 1927 Supreme Court decision, which upheld a law subjecting even illegal income to taxation, provided a potential answer to Capone’s impunity. If there were no witnesses to be found linking the boss to the Outfit’s many killings, careful, tedious investigation could link him to assets and, by extension, income he hadn’t declared or paid tax on. (Capone had no official income source.) This ruling, known as the Sullivan decision, rejected an argument that the requirement to declare illegal income violated the Fifth Amendment’s protection against self-incrimination. It remains controversial. Other legal improvisations included a city ordinance authorizing the arrest for “vagrancy” of anyone known or suspected to be a crook. (The idea was to force Capone to post bail, and then explain where he got the money.)
The violence was also becoming too much for a public that had earlier been enchanted by the “gangster chic,” and was affecting economic interests. Moreover, as the Jazz Age yielded to the Great Depression, the spectacle of fancily dressed and dissolute lawbreakers had lost its charm. With the St. Valentine’s Day Massacre, on February 14, 1929, in which seven Irish gang members were tommy-gunned to death by Capone henchmen in a Lincoln Park warehouse, and their photographed corpses made public, opinion turned decisively against him. With this, Bair writes, “the city’s moneymakers and movers and shakers were finally galvanized into taking serious action to stop the killings. It seemed there was no better way to start than to go after the kingpin who dominated so much of the fabric of the city’s life.”
There followed some innovative civil society interventions, namely the Secret Six, a group of wealthy, civic-minded citizens who mobilized resources to support state action against Capone, including putting up the money to protect and transport a key witness to South America as well as to meet the expenses for an undercover operation to penetrate the Outfit. Within this high drama were the dreary inquiries by Treasury agents into money transactions that represented “the real evidence against Al Capone.”
The Outfit’s reach was, however, still deep, and amid credible reports that the jury had been bribed, Judge James H. Wilkerson devised “a strategically brilliant solution,” dramatized to good effect in De Palma’s version, of switching juries with another judge who was presiding over a new case on the same day. An uncompromised panel, sequestered and protected for the trial’s duration, helped by a remarkably poor legal defense, ensured a conviction.
Bair’s account of the trial is detailed and vital. The tax evasion charge is often cited as a measure of the state’s commitment, more specifically how a handful of law enforcers, alone within a corrupted system, found a way to jail an all-powerful villain. But even if the trial did deliver this Public Enemy to the warden, it’s debatable whether the Outfit’s victims actually got justice. Far from representing the US criminal justice system at its best, Capone’s trial was perceived as “a trumped-up showpiece substituted for his real crimes, the uncounted ruthless and relentless killings he either committed or ordered.” In an Untouchables scene in the judge’s chambers, before the latter’s decision to switch juries, Kevin Costner’s Ness argues that Capone is a killer and will be set free by a bribed panel. But, of course, the court wasn’t trying him for murder. The actual trial, too, was replete with allusions to “the many criminal and illegal acts for which he was never charged.” While his conviction might have come as relief, the Evening Star, which Bair quotes, argued, “There will remain the sense that the law has failed.” In an earlier scene in the movie, De Niro’s Capone argues to a pack of tickled journalists, “If someone steals from me, I’m going to say ‘you stole,’ not talk to him for spittin’ on the sidewalk.” He had a point.
At the same time, for a criminal mastermind, was there not something humiliating about being sent to prison for a relatively mundane offense? For though he got away with his most serious crimes, losing in a transparent, indeed boring, legal process undercut Capone’s legitimacy. Murder, either by gangland rivals, or through extrajudicial state action, would have likely had the opposite effect; the glory of martyrdom would only have polished the Capone legend to a brighter gloss. But in Alcatraz, he was no longer Al Capone; he was the dehumanized Prisoner 85, and subject to taunts and attacks by other inmates who relished the emperor’s nakedness.
The rest of Capone’s life, and Bair’s account, is a sad Lear-like story of slow decline, as syphilis (contracted years earlier) ate away at both body and mind. While this book is uneven, and significantly more vivid about Capone’s downfall than his reign, Bair’s descriptions of how the world’s preeminent villain, once “the most shot-at man in America” (according to his very first biographer in 1930), spent his final years exercising the mental capacity of a child, close the work on a poignant note. Interestingly, a new movie with Tom Hardy about these final years is reportedly in development. If it happens, then the medium that alternately prompted us to admiration and loathing may now instill in us an entirely new feeling for this larger-than-life mobster: pity.
 Both Connell’s and Anderson’s pieces can be found in the collection, Bohemians, Bootleggers, Flappers & Swells: The Best of Early Vanity Fair (2014), edited by Graydon Carter.