By the mid-1940s, the International Longshoreman’s Association in the Port of New York boasted a membership of 40,000 workers. Most were part-time employees, and many were beholden to a particular hiring boss or waterfront gang—all of which guaranteed a desperate and compliant workforce. The ILA may have advocated for workers during labor disputes, but it also ruthlessly enforced the shape-up system, which was the foundation for the entire constellation of waterfront rackets. With thirty-two locals from the Gulf Coast to the Great Lakes and a national membership over 100,000, the ILA had become the glue that held together the vast, interconnecting array of criminal elements, making the waterfront the most lucrative underworld universe since Prohibition.
The ILA, in other words, was more powerful than any Mafia family. It was a legitimate organization with hegemony over a massive commercial and criminal marketplace. Anyone who ruled this universe was destined to be a man of great power, widely revered and feared. Such was the case for the man who ruled as the international president of the ILA for twenty-six years: a tough, proletarian individual known to his workforce simply as Boss Joe.
King of the Dock Wallopers
In all the years that Joseph P. Ryan reigned as supreme commander of the International Longshoreman’s Association, he was never once voted into office by the union’s general membership. In 1927, the year Joe Ryan first ascended to the presidency of the ILA, he was simply handpicked by a cadre of New York–based delegates representing locals from around the country. For the next two and a half decades, Ryan maintained his power, even though rank-and-file longshoremen on the West Coast completely rejected his leadership and eventually bolted from the ILA to form their own union—the International Longshoremen and Warehousemen’s Union (ILWU), which Ryan denounced as a “communist conspiracy.” In 1943, after years of strikes and labor agitation in many ILA ports from the Gulf Coast to the Northeast, the Boss was given an unusual vote of confidence: He was named “president for life”—again, not by the union’s general membership but by a proclamation of union business agents.
For a long time, Joe and his union cronies all got fat together, with Boss Joe somehow netting millions on a modest annual salary of $20,000 plus $7,200 for expenses. At the same time, he became perhaps the most powerful labor leader in the country, a benefactor to mayors, senators, presidents, and assorted killers and hoodlums. He was a kingmaker, of sorts, until his own greed and arrogance finally led the rank-and-file to rise up against him. Eventually, the public turned against him. On May 5, 1953, not long after being compelled to testify before a public tribunal known as the New York State Waterfront Commission, Boss Joe was convicted of stealing union funds and carted off to prison.
Joe Ryan’s long march to the penitentiary was rooted in his childhood. He was born on May 11, 1884 to Irish immigrant parents in Babylon, Long Island. At the age of nine, Ryan became orphaned when both his mother and father died of natural causes within a few months of one another. After languishing in an orphanage for a time, young Joe was eventually adopted and went to live with his stepmother in a cold-water flat in Chelsea, a neighborhood on the West Side of Manhattan, just south of Hell’s Kitchen.
Ryan began his working life as a floor sweeper, stock clerk, and trolley car conductor before landing a job on the Chelsea Piers in 1912. Four years later, at the age of thirty-two, Ryan joined the ILA by purchasing his union book for the going rate of two dollars and fifty cents. Within months, while working in the hold of a freighter, Ryan suffered a minor injury when a heavy sling load snapped and dropped onto his foot. Following a brief recovery in the hospital, he was assigned to the post of financial secretary for ILA Local 791 in Chelsea. Ryan would never again have to callus his hands or stain his shirt collar with sweat while working in a dock or hold gang on the waterfront.1
By most accounts, young Joe Ryan had natural talents as an administrator and organizer. Although he had dropped out of school and terminated his formal education at the age of twelve, he possessed a facility with the English language; his red-meat rhetoric was frequently humorous and sentimental. Unlike many union leaders, however, Ryan preferred to exert power mostly as a behind-the-scenes figure. In the book Dock Walloper, a lively memoir of New York’s longshoreman culture, written by Richard “Big Dick” Butler, the author describes how he tried to use then Vice President Joe Ryan as a Trojan Horse in his battles with a rival union leader.2 Butler knew Ryan well, both as head of the ILA’s district council and later as a Tammany-sponsored alderman. Knowing that young Joe Ryan had designs for obtaining the union presidency, Butler suggested to Ryan that, with the backing of Butler and others, he run against the union’s current president, T. V. O’Connor.
Ryan may have been ambitious, but not so ambitious that he would allow himself to be used in what was essentially an internal power struggle, even though it may well have propelled him to the presidency. He respectfully declined Butler’s offer, keeping both Butler and T. V. O’Connor as friends. A few years later, Joe Ryan became president anyway—on his own terms, with all of the necessary relationships and alliances intact.
With his thick torso, barrel chest, huge hands, and a face that only a mother could love, Ryan had the grizzled look and demeanor of a tough guy, but his greatest skills were as a classic Tammany-style fixer. In the mid-1920s, he formed the Joseph P. Ryan Association, a political club devoted to one thing: promoting the career of Joe Ryan. The ILA leader held fundraisers, solicited campaign contributions, and helped get out the vote for numerous Tammany candidates, including Mayor Jimmy Walker. As president of the Central Trades and Labor Council, Ryan was able to garner huge crowds for Walker at political rallies. When Beau James was forced to resign from office following the Seabury Investigation, Ryan issued a statement that read: “The labor movement in the city of New York regrets that political expediency has deprived them of a mayor whose every official act has been in conformity with the Americanistic policies of organized labor.”
From the beginning, Ryan envisioned an ILA so powerful that he would literally be able to control the fate of presidents and dictate the ebb and flow of international commerce. His plans were altered considerably, however, when longshoremen in Boston dramatically repudiated his leadership in October 1931 by going on strike against his wishes. In 1934, an even bigger labor dispute involving a dozen commercial ports from San Francisco to Seattle reached a boiling point in the ILA’s Pacific Coast District. Not wanting to be shut out like he had been in Boston, Ryan traveled to the West Coast to take part in labor negotiations with local employers. Ryan spent more than a month in San Francisco, finally emerging with a settlement that he declared was “fair and in the best interests of our members.”
The grizzled New Yorker made the rounds of various strike committees in San Francisco, Portland, Tacoma, and Seattle, urging them to ratify his settlement agreement. In every location, Ryan was voted down, and the president of the Tacoma local declared in the press, “No body of men can be expected to agree to their own self-destruction.”
The primary issue was the way in which workers were hired. Ryan urged his members to accept the shape-up system, which had been the sole manner of employment in ILA ports since the turn of the century. West Coast longshoremen astutely viewed the shape-up system not only as pernicious and humiliating for the workers, but also as the central way in which organized crime became institutionalized on the waterfront. The West Coast longshoremen preferred a hiring-hall system in which time in the hold and other seniority factors determined who was first in line for employment.
The West Coast longshoremen’s strike of 1934 went down without the support of the ILA president; it was a memorably violent and contentious affair that culminated in San Francisco with the Battle of Rincon Hill—a street confrontation between strikers, professional strikebreakers, and cops that resulted in two deaths and scores of injuries. The National Guard was called in to quell the disturbance.3
Joe Ryan left town denouncing West Coast labor leaders as mal
contents and communists, but his rhetoric could not mask what had been a crushing defeat for his leadership. Back in New York, Boss Joe sought to mitigate his West Coast failure by enforcing his will even more resolutely than before. One way the ILA president regulated who obtained power and who did not was through his ability to dispense union charters, which made it possible for groups of workers to form their own locals. Joe Ryan alone dictated who would be given this power. He allowed for the establishment of union locals only by workers who pledged absolute loyalty to Joe Ryan. They also kicked back a percentage of all monthly membership dues directly to the president for his own personal use and consumption (of course, there would never be any records to prove that this was the case).
Although waterfront mobsters tended to come in all shapes, sizes, and ethnic denominations, over a fifteen-year period, from the late 1930s to the early 1950s, the ranks of the ILA in the Port of New York became a haven for the some of the toughest characters in the Irish American underworld. Thanks to Boss Joe, many unreconstructed bootleggers found new life as dock wallopers and union enforcers through the institution of a system that was beneficial mostly to stevedore companies, union business agents, and waterfront employers, not to the workers. Individual locals broke down along ethnic lines; Italian American locals controlled business on the waterfront in Brooklyn, Staten Island, Bayonne, and Hoboken, while the Irish controlled the docks in Jersey City and on Manhattan’s West Side.
Among the many notorious members of the waterfront mob who owed their power to President Ryan were:
Edward J. “Eddie” McGrath—A former truck driver for Owney Madden and Big Bill Dwyer during the glory days of Prohibition, red-haired Eddie McGrath first became an ILA organizer in 1937, just six months after being released from Sing Sing prison. He’d been arrested thirteen times over the years on charges ranging from burglary to murder. An elite member of the New York underworld, McGrath controlled the lucrative numbers racket in the Port of New York and was believed to be on close terms with many high-ranking mafiosi. In 1943, Joe Ryan appointed Eddie McGrath an ILA adviser for life, later sending him south to shore up ILA operations in South Florida.
John M. “Cockeye” Dunn—As Eddie McGrath’s brother-in-law and designated muscle, Cockeye Dunn was perhaps the most feared gunman on the waterfront. Born in Queens, New York, he was four years old when his father, a merchant marine, was lost at sea. Dunn bounced in and out of various Catholic reform schools and was often in trouble with the law, garnering early arrests for assault and robbery. In 1932, he was convicted of robbing a card game at gunpoint and sent to Sing Sing for two years.
Once out of prison, Dunn teamed up with McGrath, who was part owner of Varick Enterprises, a front company whose main function was to make collections for waterfront boss loaders to whom every truck man on Manhattan’s West Side was paying tribute, usually in cash. The collections were enforced by goon squads armed with guns and blackjacks. In 1937, when a reluctant truck man was found dead, Dunn and McGrath were arrested on a charge of homicide but were eventually discharged for lack of evidence.
Dunn went on to form his own powerful local with the American Federation of Labor (AFL) and became the overseer of all waterfront rackets on Manhattan’s Lower West Side, which included some sixty piers. In 1947, Dunn was arrested along with two other men for the murder of a hiring stevedore in Greenwich Village; his trial was one of the more memorable events of the whole waterfront era. Cockeye was found guilty and given the death penalty. He died in the electric chair.
Andrew “Squint” Sheridan—On the waterfront, any rising underworld figure worth his salt had to have a more violent junior partner to do the dirty work. Joe Ryan had Eddie McGrath. Cockeye Dunn had Squint Sheridan, a psychopath who found his calling as a notorious ILA enforcer. Once, when a longshoreman on the West Side piers threatened to start a dissident movement and take on the union leadership, Sheridan stopped by the pier and asked the man to step into a portable toilet for a conference. There Sheridan shot the man in the head and left him to die. When another dockworker had some negative things to say about a prominent ILA business agent, Sheridan drove up in a car, walked to the platform, and asked, “Who’s Moran?” When Moran stood up, Sheridan pulled a gun, fired two shots, and killed the man in front of numerous witnesses—none of whom were willing to testify against him.
Squint Sheridan eventually became a victim of his own bad karma. In 1947, he was arrested along with Cockeye Dunn in the famous Greenwich Village murder of hiring stevedore Andy Hintz. They went on trial together and met the same fate: Sheridan was put to death in the chair just a few minutes after Cockeye, his friend and mentor.
Pistol Local 824—With Hell’s Kitchen as its base, it was no surprise that Local 824 became one of the ILA’s most powerful crews, presiding as it did over the luxury piers where the Queen Elizabeth and Queen Mary were docked. Harold Bowers was a neighborhood delegate appointed by Joe Ryan to Local 824, commonly known as the Pistol Local because its mostly Irish American membership was comprised of so many convicted felons. Bowers himself had been arrested for grand larceny, robbery, and gun possession, done time in prison, and was suspected of being an accessory in numerous waterfront murders.
The real power behind Local 824 was Harold Bowers’ cousin, Mickey, whose criminal record showed thirteen arrests between 1920 and 1940. Mickey Bowers was believed to be behind the death of (among others) Tommy Gleason, a rival for control of the Pistol Local who was gunned down in a Tenth Avenue funeral parlor—a convenient spot for a mob hit if ever there was one. Local 824 was legendary for its nepotism, with brothers, cousins, and barely qualified ex-con-in-laws first in line for lucrative administrative positions within the union.4
George “the Rape Artist” Donahue—Donahue got his start as a loading boss on the Jersey City piers and served as an ILA liaison with the political administration of Mayor Frank Hague, the least charming of all the big city Irish American political bosses. Hague’s influence reached beyond Jersey City to include Hoboken and much of Hudson County; his reign lasted from 1915 to 1949 and was militantly enforced by a famously brutal police department. Boss Hague was known to use the New Jersey waterfront as a major patronage plum, doling out jobs and favorable contracts as payback to loyal operatives. He was also tight with Joe Ryan, frequently serving as cochairman alongside New York Mayor Jimmy Walker at the annual testimonial dinner of the Joseph P. Ryan Association.
George “the Rape Artist” Donahue, Hague’s waterfront overseer, first became president of Local 247 after he and two bodyguards stormed into the Local’s headquarters and demanded the resignation of the president and vice president. When the two men refused, Donahue pulled out a gun, stuck it in the president’s mouth, and told him either his signature or brains would be on the resignation papers. The president signed away his leadership. When the vice president hesitated to sign, his front teeth were knocked out with a gun butt. He also signed.
Donahue’s leadership of Local 247 was marked by violence. When Boss Hague left office in 1949, after a thirty-four-year run, Donahue lost much of his clout. In January 1951, a bomb went off under the hood of his automobile when he started the ignition. Miraculously, Donahue survived unhurt, but his days as president were numbered. He was lucky to live to see retirement.
Many of the hoodlums, union men, and politicians who operated within the Port of New York were rulers in their own right, but none could hold a candle to Boss Joe. On a daily basis, Joe Ryan’s ILA created the illusion of democracy; there were local meetings, district councils to hear complaints, an ILA executive board, and a national convention held every year. But none of that mattered to Ryan. If ever he harbored aspirations for a unified workforce, for whom he would be a magnanimous advocate, those dreams were crushed in Boston and on the West Coast, when his attempts to negotiate a strike settlement had been so dramatically repudiated.
Boss Ryan was determined to show that such humiliation could never occur on his home turf. In the Port of
New York, thanks to his unprecedented gathering of ex-cons, killers, and various political sycophants, his authority would remain absolute.
You Push, We Shove
In the long history of the American labor movement, the ILA was not alone in its use of hard men and questionable tactics. The reasons for this are buried deep in the history of America’s industrial beginnings and inexorably intertwined with the Irish American experience.
Before Joe Ryan ever rose to the top of the longshoreman’s association, labor politics in the United States were steeped in bloodshed. Among the first laborers in the country to become advocates for basic principles of employment such as a minimum wage, safe working conditions, and some version of Workman’s Compensation were Irish immigrants and Irish Americans. Paddy dug the canals, built the bridges, and, along with Chinese, African American, and Italian laborers, laid down the tracks of the transcontinental railroad. The work was brutal and often lethal. In the anthracite coal mining region of Pennsylvania, black lung disease and mining accidents took the lives of thousands of workers, including more than a few under the age of ten.
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