In January 1935, Pendergast began a series of meetings with a St. Louis insurance broker who was looking to influence legislation in the state of Missouri. Pendergast had considerable pull with Robert Emmett O’Malley, the superintendent of insurance for the state. For a price, Pendergast told the St. Louis broker, he could make his troubles go away. The man readily agreed, promising a series of payments to Pendergast and O’Malley totaling $750,000. The first of these payments was made at Pendergast’s political headquarters. Another payment, totaling an astounding $330,000 in cash, was made at a Chicago hotel and later delivered directly to Pendergast at his home, where he counted out the bills on his dining room table.
In all, Boss Tom received a grand total of $440,000, keeping $315,000 and giving $125,000 to O’Malley. Technically, the money did not constitute a bribe. Pendergast and the insurance broker had merely engaged in a classic form of American-style influence peddling. If the boss had paid federal income taxes on the money, there would never have been any problem. But he apparently used the entire amount to settle pressing outstanding debts owed to bookmakers.
Pendergast’s shady insurance kickback lit a fire under the Goo Goos and antimachine crusaders. For the first time, Pendergast candidates for office began routinely losing at the polls, leading the governor of Missouri, Lloyd C. Stark, to declare, “The political boss can be licked. He and the corrupt machine are in the main responsible for organized crime in our cities. I propose to lead the fight against Boss Tom Pendergast and keep at it until Kansas City is cleaned up.” Keeping his pledge, the governor put pressure on President Franklin Roosevelt who, in May 1938, answered Governor Stark by unleashing investigators from the Bureau of Internal Revenue Services on Tom Pendergast and his Machine.4
In April 1939, after months of investigation, the IRS went public with their findings: In a period from 1927 to 1937, the Boss failed to report as income the staggering figure of $1,240,746.55, defrauding the government of $501,078.75 in taxes. Tracing all of the money that Pendergast had received proved difficult, said the investigators, since he kept “negligible records, rarely used a bank account, almost always accepted only cash payments, made virtually all expenditures in cash, and sent large amounts by wire under assumed names.” They were able to determine, however, that, in 1936 alone, Pendergast wagered $2 million on horse races and lost $600,000. In 1938, he lost $75,000 in November and won back $43,000 the following month.
On April 7, 1939—Good Friday—a federal grand jury indicted Pendergast on two counts of tax evasion. The boss, more corpulent than ever, his hair now thinning and gray, appeared in court to be fingerprinted and to give bond. He was unrepentant. In an uncharacteristic display of self-pity, he snarled at reporters and compared himself to the Man from Nazareth: “There’s nothing the matter with me. They persecuted Christ on Good Friday and nailed him to the cross too.” Later, in a more reflective mood, he said, “Every human being, including myself, has to live with his own conscience. There comes a day when he has to account for himself. There’s no one there but himself. It’s a fearsome time when a man faces his own conscience. But I’m willing to live with mine. I haven’t an elastic one either. I’m living with my conscience today in peace and contentment.”
A month after the indictment, to the surprise of many, Boss Tom entered into plea negotiations with the prosecution. Suffering from a chronic heart condition, he did not look forward to a contentious, embarrassing trial that he could not win. There was also the threat of other indictments directly related to the insurance kickbacks. Consequently, Pendergast pleaded guilty in exchange for a sentence of fifteen months in federal prison. In addition the judge announced, “The defendant will not be permitted to bet on the races or gamble in any form. He will not be permitted, directly or indirectly, to take part in any sort of political activity unless his full civil rights shall be restored by presidential pardon. He will not be permitted to visit 1908 Main Street during his probation.”
Tom Pendergast served his time in prison and lived out his remaining years in ill health. In keeping with the terms of his probation, he steered clear of politics (although his nephew James Michael Pendergast kept the family name alive in Missouri politics well into the 1950s). On January 15, 1945, at the age of seventy-two, T. J. suffered a heart attack in his office at Ready-Mixed Concrete. He was rushed to the hospital and passed away the following day.
In death, as in life, Pendergast inspired extreme points of view. His family had played a major role in the political and economic fortunes of Kansas City for more than half a century; Boss Tom presided over this dynasty like a portly potentate. To some, he was the devil incarnate. Wrote one local judge who’d butted heads with Boss Tom:
He thoroughly understood the psychology of the underworld, and the habitues of the shadowy kingdom followed him blindly as well as devotedly. He protected them from prosecution for their misdeeds and granted them commissions to sin against the laws of God and man. His past experience had qualified him to lead and rule the refuse in society. He understood the life of the brothel and houses of ill fame…. He derived immense revenues from graft in public office and from his levies on crime. To support his invisible government, he deemed it prudent to increase his power over elections and to take away every element of chance…. All citizens, to be secure, were forced to acknowledge the uncontrolled and despotic power of one man with his invisible empire.
Pendergast loyalists, of course, saw things differently. At his funeral, attended by an enormous crowd that included Vice President Harry Truman (whose career Boss Tom had initiated and sponsored), a Catholic priest eulogized the deceased. “He had a noble heart,” said Monsignor Thomas B. McDonald. “His word was his bond. If he was your friend, he was a true friend. In regarding his life, it would be best to recall the injunction, ‘Let he who is without sin cast the first stone.’”
T. J. himself, in an interview published in the St. Louis Star-Times just a few months before his death, gave the best defense of his regime. With his usual mix of arrogance and Christian piety, he proclaimed, “I’ve done a lot for Kansas City—for the poor of Kansas City. I’ve done more for them than all the big shots and bankers, all of them put together. We used to take care of our poor, with coal and wood and food and rent, and we helped them in their trouble. We never asked the poor about their politics….” Finally, in what could be his epithet, the boss declared, “And I’ve never broken my word. Put this down: I’ve never broken my word to any living human being I gave it to. That is the key to success in politics or anything else.”
Reform
The prosecution and banishment of the political bosses—Walker, Hines, Pendergast, and others—was only one factor in the decline and fall of the Irish political machines. From the beginning, the New Deal had been designed as a federal system to dispense the same sort of services that had once been provided by political organizations like Tammany Hall at the ward level. Federal work projects, food stamps, and low-income housing were functions of the New Deal that had once been monopolized by Irish-run machines for close to a hundred years, when no other organization within government seemed to give a damn. Over time, the general public grew weary of seeing bosses like Sullivan, Croker, and Pendergast get rich off backdoor deals in smoke-filled rooms, which sometimes involved mobsters and a primitive form of muscle. In the brotherly glow of the New Deal, such operations seemed perversely out-of-date.
Even the Irish had seen enough. One hundred years after the Great Potato Famine, which had facilitated the birth of the American underworld, the Irish no longer needed the fierce upperhand that had been provided by the political machines. As a group, the Irish had made inroads into virtually every profession in American life. Moreover, they had a controlling interest in many of them, especially municipal professions such as police forces, fire departments, and public works. Quite simply, by the mid-twentieth century, the political bosses were no longer needed. As they dropped off one by one, the attitude among many second and third gen
eration Irish Americans was “good-bye and good riddance.”
For the Irish American gangster, however, the end of the Machine as a powerful political entity was bad news indeed. The Machine had helped to keep the underworld organized and stratified. Street-level Irish hoodlums, those who had survived the bloody purges of the Prohibition years, rose up the social ladder thanks in part to their association with various Machine-affiliated political organizations. Now that they were in decline, the Irish gangster had nowhere to turn. The only organization out there now was some version of the mafia, variously known as the Syndicate, the Outfit, or Cosa Nostra. From here on out, Irish American gangsters looking to do business in the underworld would be doing so over some variation of pasta and meat sauce.
The culture that had spawned and sustained the concept of the Irish American gang for so long appeared to be dying out. This gradual social metamorphosis was institutionalized on June 22, 1944, when President Roosevelt signed into law a piece of legislation that, inadvertently, probably had more to do with the death of Irish American gang culture than any other single factor. It was called the Servicemen’s Readjustment Act, otherwise known as the G.I. Bill.
Since the days of the Civil War, military service had been a possible alternative to the gang life, an arena in which physical aggression and other violent tendencies were given an acceptable outlet. Wars ended, however, leaving the veteran with sometimes troubling memories and few adaptable job skills, which put him right back where he started. What the G.I. Bill did was make military service attractive by offering money for education and housing to veterans. For many young Irish American males raised in a culture where violence, early alcoholism, and machismo comprised the true Holy Trinity, the G.I. Bill offered a clear path out of the ghetto. Irish Americans, perhaps more than any other ethnic group, took advantage of the benefits provided by the bill, leaving behind in droves the street-level gang mentality that would now be adopted by Puerto Ricans, African Americans, Asians, and other ethnic groups.
Given the powerful social forces that conspired to stamp out the Irish American underworld, the Irish mobster appeared to be on the verge of extinction. Like the Paleolithic creatures of a previous age, however, Irish mobsters would prove to be a pesky, irascible organism whose carnivorous ways would continue to sustain them long after the ecosystem at large had passed them by. While the political framework that had given rise to the Irish mobster may have been rendered obsolete through prosecution and political reform, independent Irish mobsters lived on—feasting, as before, on rackets associated with organized labor, police graft, gambling, narcotics, murder-for-hire, and, of course, politics.
The extinction of the Machine was not the final blow; it was merely the shedding of a layer of skin. The foundation of the Irish American underworld, dictated by a flexible morality that involved manipulation, coercion, subterranean alliances—in a word clout—was alive and well. With the machine structure now cast off, the Irish American way of doing business, heretofore restricted to the ward, the city, and the state, was now free to range far and wide and advance to new heights. And so it would—all the way to the White House and beyond.
PART two
a long way from tipperary
CHAPTER # Eight
8. hard hats & hard men
From the earliest inception of the Irish American underworld, the waterfront was where it all went down. In any port city the pattern was the same: Immigrant ships arrived at the docks and unloaded their human cargo. Native-born Americans and wily immigrants who had arrived years earlier were there to meet the new arrivals. Like jackals gathering for a feed, hustlers, con artists, sneak thieves, and wharf rats descended on their prey. Even the official greeters who represented legitimate social organizations like Tammany Hall had ulterior motives. Sure, an immigrant runner from the river wards might lead a new arrival past the riffraff; he or she might suggest lodging or a place to find a bowl of soup and a piece of bread. But it all came at a price. By partaking of the immigrant runner’s largesse, the greenhorn had virtually sold his or her soul to the Machine, knowingly or not.
The waterfront was not only a port of entry, but also a vast commercial bounty. Especially in the decades before commercial trucking, seafaring ports were the primary source of national and international trade in the United States. Valuable cargo of every variety—including illegal contraband—arrived and departed by way of the docks. Organized pilferage, a huge racket for the gangsters, was considered the price of doing business; the losses were part of an inflated bottom line that was passed along from the stevedoring companies to the consumer. Luxury cruise ships of the Cunard and Grace Steamship lines were another wonderful source of exploitation; they paid huge tariffs and disgorged an unending supply of well-to-do passengers who, in the eyes of the gangsters and their facilitators, were ripe for the taking.
Most of all, the docks represented jobs. A steady supply of manual labor was needed to service the vast commercial machinery along the waterfront. A young, brawny lad with little or no education could, by cultivating relationships with the right people, find work loading and unloading freight. Eventually, through organized labor agitation, waterfront jobs became a highly prized, well-paying form of employment, especially for unskilled laborers with few other opportunities.
On wharves and docks throughout America, tough men gathered on a daily basis. Among them were the poor, immigrants, ex-cons, and those simply looking for a solid day’s work, a bimonthly pay packet, money for rent, shoes, a warm winter coat, a beer-and-a-shot, or food and sustenance for their families at home. There were never enough jobs to go around. To procure a day’s wages, a strong back and conscientious work habits were not the primary consideration. More valuable was a man who knew the routine, who showed a willingness to submit to the System as it was—a system based mostly on greed, exploitation, and the threat of violence.
The shape-up was a ubiquitous method of employment on the piers. Men arrived twice a day and gathered in a huge mob outside a designated loading dock. A stevedore, or hiring boss, surveyed the crowd and decided who would work and who would not. If you were a lone, unaffiliated individual looking for a day’s labor, fuggettaboutit. The only way to procure work was to form into a crew or gang and pay tribute to the hiring boss, who in turn paid tribute to the stevedore companies, who in turn paid tribute to union officials, who in turn paid tribute to politicians and cops, and so on up the ladder. The result was an elaborate kickback system with tentacles that reached into virtually every aspect of modern industrial society—in other words, organized crime in a nutshell.
In the early decades of the twentieth century, Irish and Italian laborers waged a bloody battle for control of the commercial piers in many big cities. The Brooklyn dock wars, led by Wild Bill Lovett and Peg Leg Lonergan, may have produced the highest body count, but similar battles sprang up all over the United States. In New Orleans, huge shipping companies deliberately manipulated Irish and Italian longshoremen, pitting one against the other, eventually adding a new element—African Americans, who were brought in at low wages to undercut both groups. In New England, some of the cities’ most renowned gangsters got their start in the region’s dock wars, shuttling from Boston to Providence to Portland, Maine during strikes or when competing work crews clashed. In the Great Lakes region, particularly in Chicago and Cleveland, Irish American longshoremen fought to hold onto jobs that had passed from one generation to another since at least the 1870s, when Irish laborers first arrived in sizable numbers to help build the Ohio and Erie Canals.
Of all the locales where gangsters fought and eventually seized control of commercial mechanisms along the waterfront, none compared with the Port of New York. By the 1940s, especially during the years of World War II and immediately after, the Port of New York emerged as the most lucrative commercial port in the world. The shipping business in New York and elsewhere had survived the lean years of the Depression, which saw a dwindling workforce and a number of crippling stri
kes. Labor subterfuge and political turmoil may have kept workers from organizing, but it also hindered commercial trade on the waterfront. From an international standpoint, strikes and violent confrontations between workers and police made shipping freight more trouble than it was worth.
All of that changed on December 7, 1941, when the Japanese air attack on Pearl Harbor initiated U.S. involvement in World War II. Among other things, the war years turned out to be an unprecedented boon to the maritime industry, with New York harbor at the epicenter of an economic revival that would continue for at least the next fifteen years.
At the time, the Port of New York included all seaborne commercial activity in Manhattan, Brooklyn, and New Jersey, a gigantic waterfront trade covering 750 miles of shoreline with 1,800 piers. By the middle of the decade, nearly 10,000 ocean-going ships cleared New York harbor a year, or one ship every fifty minutes. These ships were owned and operated by steamship lines that sailed to 155 ports in every corner of the world. With more than a million passengers a year, they carried thirty-five million tons of cargo in foreign trade alone.
Within the harbor itself, cargo handling was serviced by approximately 2,500 tugs, barges, lighters, derricks, car floats, and scows. The adjacent railroad fleets moved more than 750 carloads of export freight daily to 200 steamship piers. Domestic freight was believed to be four or five times higher than foreign trade, with a total cargo somewhere around 150 million tons annually. New York harbor handled between 32 and 38 percent of the nation’s overall cargo, or money cargo in longshore terms, with an annual value that ranged from fourteen to sixteen billion dollars.
This huge flow of commercial activity was bound to attract its share of criminal parasites and bottom feeders. In fact, many sluggers, shoulder hitters, and bootleggers who had survived the Prohibition years drifted into rackets associated with the waterfront trade. The hiring boss, in particular, was frequently a gangster from the booze running days who was adept at attracting and also controlling “dock wallopers.” The docks were a rough-and-tumble universe; shylocks, or loan sharks, fronted money to workers so they could pay tribute to the hiring boss. Workers who were tardy in repaying the loans could be roughed up or even killed. Longshoremen who were on the wrong side of labor disputes also became victims of violent intimidation. And everyone kept their mouths shut; killings on the waterfront almost always went unsolved. Violence became the underpinning of a vast racketeering underworld that included gambling concessions (bookmaking and policy), payroll padding, no-show jobs, organized thievery, murder-for-hire, and all manner of labor corruption.
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