“I don’t want to bore you, Nuala,” I said, hurt that she was making fun of my habit of occasional background lectures on her new country.
“Och, Dermot,” she said, her hand squeezing mine, “if you stop being a writer, wouldn’t you make a wonderful teacher, and wouldn’t that keep my eejit brother quiet for a while.”
“Well,” I said, mollified by her flattery and her smile, “you must think of the first bootleggers as being not unlike the black and Hispanic drug gangs today.”
Not unlike! That was pompous and professorial and from a guy who hated classrooms, which is why he flunked out of Notre Dame.
“Uh-huh.” She gazed at me with rapt adoration, which I did not deserve.
“They were people at the low end of the economic ladder, often without much prospect of getting up it. Suddenly a new market appears and they gingerly test the waters. They are astonished at how much money they can make in a short period of time. At first the only people to fear are the law-enforcement types who are either overwhelmed by the amount of criminal activity or corrupted by it. Then as their greed expands, they begin to fear one another. The next step is killing, first of all, as they justify it, to protect their turf, and after a while to take over someone else’s turf to which they figure they have a right. It gets dangerous, kill or be killed. Kill them before they kill you. These are all young men, still in their twenties and not troubled, any of them, by much in the way of conscience. They are, in other words, a new generation of American entrepreneurs on the way up. They tell themselves that they are no worse than the rich Protestants who are already ripping off the country or the hypocritical cops who are extorting payoffs from them. They are simply businessmen who are providing a public service, selling goods that people want.”
“Do they really believe that, Dermot love?”
“Hard to say, Nuala. Up to a point they do. And despite movies like The Godfather, they weren’t all Italians. There were Irish gangs and German gangs and an occasional Polish or WASP gang. The Italians, however, had a couple of advantages. Like the blacks today they were the poorest of the poor, they brought the Mafia tradition of secret societies with them, and they were the most ruthless of any of the gangs. Capone was no brighter than anyone else. His secret of success was that he was the most ruthless of them all. He killed without hesitation and without guilt.”
She shivered. “One of your borderline personalities, was he now?”
“He used to like inviting someone who had offended him to dinner, then have his guys suspend the victim from the ceiling, and beat him to death with a sawed off baseball bat … When he came to Chicago, he went to work for a man named Big Jim Colosimo, a major bootlegger and ‘speak’ owner. A ‘speak’ was a ‘speakeasy,’ a saloon which was technically illegal but paid off the cops and provided big-time jazz music as well as booze. They called it a ‘speakeasy,’ it is said, because you had to speak softly when you entered the club. Capone and his friend Johnny Torrio killed Colosimo because he stood in the way of the expansion of the liquor trade.”
“Ugh.”
“Originally, the Mafia was a kind of vigilante group which in effect became an alternative government in the old Kingdom of Naples. It enforced the law and order and kept the peace and meted out justice, all of which the corrupt administration in Naples could not do, much like the IRA does in some places in Northern Ireland, and Ribbon Men and the White Boys before them.”
“You know more Irish history than I do, Dermot.”
“That’s because no one forced me to study it … Anyway, it was only a slight change for them to apply the same rules, along with the same secret oaths and the other rituals, to the situation in this country. They were only another government, less hypocritical than the legal one as they saw it, protecting their own interests in a chaotic situation.”
“So Capone was kind of Sicilian warlord?”
“He probably thought of himself as kind of warlord and protector of his people, but I just learned he wasn’t Sicilian. His family was from Naples, which was a bit of a problem for him at first. Then he killed so many people that it didn’t matter where he came from. You gotta remember, Nuala, that these were not the wise old men you see in the films and TV, the dons who have survived a long life of crime. There were no dons in those days, only the wild and half-crazy young punks who believed they were immortal. Capone ruled Chicago by the time he was thirty.”
“So very much like the street gangs today?”
“Even up to the drive-by shootings. Capone’s guys would drive by a speak that was buying someone else’s booze and spray it with their Thompson submachine guns—tommy guns as they called them. If the owner of the speak survived, he changed his mind about who he would buy from.”
“And they thought they were just businessmen?”
“So they said. And very successful businessmen at that. If some of the drug kings survive for another twenty years, they may become old wise guys as did the few Italians who survived Prohibition and turned to gambling and vice, extortion, and eventually drugs to make their money. Crime, they had discovered, any kind of crime, was too easy a way to make money for them to give up. They also branched out into legitimate or quasi-legitimate business—movie theaters, unions, laundries, liquor stores, real estate, auto dealers, even banks. Eventually, their criminal activities and their legitimate ones became so intertwined that they probably couldn’t keep them straight in their own heads. They were always willing to use violence in their legitimate business, too. Scare off a rival laundry or racetrack tip sheet by wrecking some equipment and maybe killing a couple of people, if you really had to. Many of the major banks in Chicago appointed a vice president in charge of dealing with the Outfit. They still had their gang wars, they still killed, but they had learned the ways of prudence. You killed only when you had to, not for the sheer fun of it.”
“So that’s what the Mafia is today?”
“We don’t use that word much here in Chicago. Nor do we ever use ‘La Cosa Nostra’—Italian for ‘Our Thing’—which is mostly a media word. We call them the Mob, or the Outfit or the Boys, sometimes the Boys on the West Side. They usually don’t try to fight the street gangs these days, because they think it’s too dangerous a way to make money.”
“OK, I think I understand so far.”
“They were not and are not nice people, Nuala Anne. The novels and the movies glorify them but they are nothing more than sociopaths, evil men without conscience and without morals.”
“Some of them still live in River Forest, don’t they? Do any of them belong to the country club?”
“No, we don’t let them in, any more than the WASPs let the Irish in a half century ago. Some of their kids maybe, especially a daughter that married out of the Mob. We don’t draw the line on the bankers or the politicians or the ‘legitimate’ businessmen that deal with them … But this gets us ahead of the story. No one was thinking country club in those days nor new business ventures. They were only a crowd of ruthless young guys out to make a lot of money in a hurry. American society had provided them with a perfect opportunity.”
“Just like you Yanks do for the drug gangs today.”
“Arguably, as your friend the little bishop would say. At first they bring in a truckload from Canada to help out a friend at a speak who was running short. Then maybe a couple of truckloads. Then they discover there were guys like themselves all over town doing the same thing, guys from the North Side and the West Side and the South Side and from Northern Indiana and Italians and Irish and Jews and, like I say, a few Poles. So they join forces with some of them to drive others out of business with threats and an occasional salutary murder. They use their combined resources to buy off cops and public officials and open or reopen breweries in Chicago. Capone eventually owns the working-class suburb we call Cicero and practically owned Chicago. So primitive capitalism turns into economic oligarchy and eventually, as Capone kills off more and more rival gangs, a virtual monopoly. There was onl
y one guy in town who was as tough as Capone, as ruthless, as ready to kill.”
“And that was Sweet Rolls Sullivan?”
“You got it. He’d been a killer for an even longer time than Scarface Al. And murder no more troubled him than it troubled Capone. They were the perfect match in that respect. In every other way, however, they were as unlike as two men could be.”
“And isn’t that an article about him that you’re holding there in your hand?”
“Tis,” I said, imitating her sigh.
“And you’d be expecting me to read it before the evening is over?”
“Before we leave here.”
She grinned at me, took the article, and called to the bar person, “Sonia, your man wants two more Bailey’s on the rocks. Make those double Bailey’s.”
(Chicago History, Spring 1970)
SWEET ROLLS SULLIVAN: THE LAST OF THE IRISH GANGSTERS
By Timothy Patrick McCarthy
The Italian bootleggers called him “Sweet Rolls” because he owned a bakery in the 700 block on North State Street. His own men called him “Red” or sometimes “The Little Fella.” His wife called him “Jimmy Dear.” Chicago cops called him “Killer Sullivan” or sometimes, half-admiringly, “Dago Killer,” because he had wiped out so many of Scarface Capone’s hired guns. On the day of his funeral, the largest till then in Chicago gangland history, Federal cops called him the last man who might have stopped Capone’s drive to dominate Chicago crime, and for all practical purposes Chicago itself.
“We all thought the redhead was as tough as Capone and a lot smarter too,” a reporter for the Chicago Tribune remarked as the funeral cortege pulled away from Immaculate Conception Church on North Park Avenue on that gray September day in 1927. “Marriage must have softened him up. Too bad.”
Cops, reporters, habitués of the most expensive speakeasies in the city, and the other hangers-on in the demimonde between the bootleggers and what remained of law-abiding society were placing bets on who would kill whom first. The smart money was betting on Sweet Rolls Sullivan, the wish perhaps being, as Sullivan himself might have said, the father of the thought. Sweet Rolls killed with no more scruples than Scarface did. But he wasn’t crazy. If he had taken over from Capone, the rest of the Prohibition era in Chicago would have been relatively peaceful.
The bets were not unrealistic. Only three weeks before forty-five caliber bullets tore gaping holes in James Xavier Sullivan’s chest, gunners allegedly from his gang gunned down three of Capone’s henchmen as they came out of the Lexington Hotel on South Michigan Avenue, which was Capone’s headquarters. With characteristic sorrow for the death of his soldiers, a horrified Capone said to reporters, “It might have been me.”
As it turned out, Sullivan signed his own death warrant when he failed to follow up the “Lexington Hotel Massacre” with the killing of Scarface himself. To this day no one is sure why he didn’t take advantage of the temporary disarray in the Capone gang.
Popular history has it that, long before Prohibition, the Chicago Irish made their money in politics and government jobs, in which activities they were not averse to making a dishonest buck. While it is true that the Irish did not need Prohibition to become successful Americans, it is not true there were no Irish criminal gangs. Long before the Italians came to America, Irish gangs flourished in this country.
The legendary Spike O’Donnell was probably the first Chicago bootlegger. Long before the Outfit, as Chicagoans call the crime syndicate, moved into the sale of illegal liquor, indeed before there was an outfit, O’Donnell saw the possibility that the Volstead Act had created. A two-bit gang of burglars and fixers, O’Donnell’s mob quickly became wealthy beyond their dreams. When Capone’s tommy guns silenced several of his allies, O’Donnell saw the wisdom of early retirement. The Irish made lots of money off what President Hoover would later call the “Noble Experiment” of Prohibition, but they made it as recipients of bribes from the bootleggers. However, this neat paradigm leaves out the enigmatic and fascinating Sweet Rolls Sullivan who gathered together the remnants of the O’Donnell gang, added his own followers, and fought Scarface to the end.
He was an equal-opportunity employer, too: his gang included members of most of Chicago’s ethnic groups, blacks, Mexicans, and two northern Italians who despised any “monkey” from south of Rome.
Sullivan was a Democrat and Capone was a Republican, though they paid off candidates and office holders from both parties. Like the good Republican he was, Scarface favored the continuation of Prohibition, a policy which was assuredly good for his business. Sweet Rolls was a “wet.” Prohibition, he told reporters, was an attempt by Protestant Americans to enforce virtue on the rest of us. “We’re going to have to pay a heavy price for that in the years and decades to come.”
Asked what he would do if the bootlegging business dried up, he replied, “Work full-time in my bakeshop.”
No one was sure whether he meant it. The redhead loved to joke and rarely said what he meant or meant what he said. Still he did lay claim to both civic and religious virtue. He went to Mass every Sunday, was married by a priest, contributed heavily to Catholic causes, especially St. Mary’s Training School in DesPlaines, and supported the Chicago Symphony and the Chicago Opera Company. In his role at the Opera Company he occasionally would bump into the Company’s great patron, utility magnate Samuel Insull. Chicago legend has it that Insull once arranged a private dinner for himself, Sullivan, and crusty George William Mundelein at the Archbishop’s house on North State Parkway. Nothing came of this odd ménage à trois, because, while Mundelein did not like Italian criminals he saw little difference between them and Irish criminals, even if, as one of the Archbishop’s staff later would comment, the Irish crooks at least knew how to use knives and forks.
When Sullivan was gunned down, spilling his blood on a large birthday cake he had made for his wife Marie, Mundelein denied him a Mass at Holy Name Cathedral, across the street from his bakery, and Catholic burial. The pastor of the little church on North Park, a man of such advanced age that he did not fear the Archbishop, agreed to say the Requiem Mass in his church, though, in deference to the Cardinal, he did not accompany the body to Mount Carmel Cemetery. Such defiance of an Archbishop, especially such a lordly, would-be Renaissance prince, was most infrequent in those days.
Legend has it that the gravediggers at Mount Carmel threw dirt from a section of the cemetery which had not been blessed into Sullivan’s grave to honor the rule which forbade the burial of criminals in “consecrated” ground.
“Tis true, Dermot Michael, about the unconsecrated ground?”
“True enough, I fear.”
“Didn’t it bother your grandparents that their grave would be next to this Sullivan person?”
“They thought it was funny.”
“Did they know him?”
“They were vague about that. They did say once that he was not the worst of them.”
“Maybe,” Nuala suggested, “they knew his body wasn’t in the ground, at all, at all.”
“Maybe.”
Details about Sullivan’s past are hard to find. He claimed to come from County Cork, from a town just outside of the city, and to have worked as a lad in a bakery in Cork. His death certificate lists Cork as his place of birth. Those who remember hearing him talk, however, say that he lost the rich Cork brogue if he ever had it. The files containing his marriage records have disappeared mysteriously from Immaculate Conception Church on North Park. There is no evidence that he ever became an American citizen or that he entered the United States with a valid passport. There are four bakeries in Cork with Sullivan as a name. Only two of them date back to the first decades of this century. At one of them there is no family memory of a Jim Sullivan, if that were his real name, who migrated to America. At the other bakery, there is a vague recollection of a cute kid with red hair named Jimmy, Jimmy Ahern to be precise, who worked there during the years before the Great War.
“Ah, was
n’t he a cute little darling,” said an elderly woman, whose family kept the public house across the street. “Always smiling and eager to please? And didn’t he work terrible hard and didn’t they say he was a great baker, whatever that means? But his name wasn’t Sullivan, though it was Sullivan’s Bakery all right. And weren’t they terrible hard on him, making him work eighteen and even twenty hours a day and never letting him go to school.”
Why was he treated so harshly? The thin memories of the past say that he was an illegitimate child, son of a young woman who was “no better than she had to be and her kind never had to be very good at all, at all.”
When the woman died, Jimmy was only seven years old according to the legend. The Sullivans were relatives of his mother in Cork City to whose care she had committed her son. That must have been about 1905.
Did he ever learn to read and write? He must have because there was no doubt about his ability to read in Chicago two decades later. He gave the impression of being a well-educated man, though one whose choice of words suggested that he was an autodidact. Perhaps his mother taught him to read before she died, though if that be the case she must have been something more than a common trollop.
The vague Cork memories say that he enlisted in the British Army in 1914 just after the war started. Doubtless he lied about his age as many young Irishmen did in those days, figuring that life was easier in the trenches of Flanders than in the poorhouses of Ireland. There is a record of a man in London named James Sullivan from Cork who enlisted in December of 1914 and served as a baker. At first.
The Cork legend says nothing more about him, save for dubious rumors that he was some kind of hero. The army record indicates that James Sullivan served in France for four years until the very end of the war, at first as a baker and then as an infantry noncom and then as an officer. With the exceptions of an occasional leave to go “home,” wherever that might have been, he seems to have spent most of those four years in the trenches. He won just about every medal England had to give him, except the Victoria Cross, and he seems to have been recommended even for that after the massacre at the Somme (or Paschendale, as the English call it). He was seriously wounded on the third day of the battle, but survived to lead a company in the final battles of the war. Apparently they didn’t give the V.C. to Micks. He was demobilized almost four years to the day after his enlistment as Major James P. Sullivan, D.S.O. He was twenty-three years old according to the English records and only twenty if one believes he was truly born in 1898.
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