Like the lawlessness of the Old West, the era of Monk Eastman in the “Wild West” gangland of the Lower East Side had passed into history, his death signaling the last rites for the old-style gangs and the dawn of the new age of organized crime. Although gangsters still strode the streets of New York, they were of a very different breed. Monk had priced his jobs at a handful of dollars and always liked to keep his hand in by inflicting an odd beating himself, a habit that put him on the path to his downfall. His successors walled themselves off from the violence perpetrated by their minions and, fueled by the liquor gold rush of Prohibition, became extremely wealthy, if not wholly respectable, businessmen.
Rooted in the “romantic” East Side past, public perception of the modern gangsters lagged behind the reality. Writing fifteen years after Monk’s death, the Pulitzer Prize–winning reporter Meyer Berger remarked that most people still thought of gangsters and racketeers as “loafers with turtle-neck sweaters, cauliflower ears and protruding maxilla, who beat their women and punt their offspring around the flat. That type passed out of existence during the liquor gold rush … Your modern racket boss, when he isn’t in Miami to avoid embarrassing questioning by loutish policemen … if he kicks mamma around once in a while, for old time’s sake, he does it in the privacy of his own home.”1
Old-style gangsters might mutter scornful remarks into their beers about gang bosses with secretaries, receptionists, and smart offices in fashionable districts, but these new gangsters wouldn’t have dreamed of dirtying their manicured hands with a little Monk-style street-fighting; they enjoyed wealth, power, and influence beyond the dreams of Monk Eastman in his prime. They resented being described as gangsters and preferred to describe themselves as businessmen and their gang as their organization.
As Meyer Berger sardonically noted, “the muscle” used for intimidation or to carry out the murders that were incidental to the business were not allowed to “clutter up the premises, because it wouldn’t look nice,” and most of the racket bosses also aspired to a place in society commensurate with their wealth. Ciro Terranova, the boss of the Harlem rackets, loved
a canter in the park or among the lovely hills of Westchester, because you meet such interesting people on the bridle path … The East Side crime-school graduates, once devoted to pinochle and stuss, have taken up bridge … and discuss end-plays and squeezes with as much zest as they used to discuss a particularly neat skull fracture or eye displacement … Born in cold flats on the East Side and accustomed to taking their night’s ease on pool tables when the skull-fracturing and nose-busting wasn’t paying dividends … the present big-shot bosses are making up for it in the most luxurious penthouses in the city.2
The few survivors of the old gangs and the old ways, like Humpty Jackson—when last heard of, the owner of a Harlem pet shop—could only shake their heads at the way things had changed.
Like the Dead Rabbits and Whyos before him, Monk had been an old-school gangster, fighting and brawling his way to the top of the heap and leading from the front in the bloody, brutal gang battles to consolidate his power. Yet he also anticipated the modern gangland era, developing the sophisticated rackets that his successors would utilize and overseeing the organization of rival gangs into federations that might sometimes feud with one another, but could also collaborate for their mutual benefit. He created the template and laid the foundations that Murder Inc., the Syndicate, and the Cosa Nostra would build upon.
He was undoubtedly a gangster, a bruiser, a burglar, a liar, a thief, a thug for hire, a pimp, and an occasional opium peddler, but the litany of his crimes and misdemeanors does not begin to tell the full story of Monk Eastman. He covered his tracks so well that even the most basic facts of his existence were open to question. Barely anyone knew his real name, his genuine age, or his true address. Even the police showed themselves unable to keep track of all his numerous arrests and convictions under a string of aliases, and they continued to file his records under “William Delaney,” believing to the end that it was his real name. They also believed that he was illiterate, but it stretches credulity to imagine that a man who could not read would have had newspapers delivered to his cell or required his subordinates to produce written reports of their crimes. Nor, if he was merely an ill-educated thug, would he have taken time to save a young sailor from his own youthful folly on the Bowery—an act of kindness the man still remembered and treasured twenty years later—nor risked his life to rescue his wounded comrades on the battlefield, nor intervened to prevent another member of his company from taking the life of a terrified German boy soldier. His army comrades had no doubts about Monk’s character, and their feelings must have been shared by those thousands of poor citizens of the Lower East Side, the majority women, who traveled across the East River to Williamsburg and Cypress Hills and stood for hours in the bitter winter cold just to attend his funeral.
No matter how cynical his motives or how illicit his means of earning money, Monk—like his old political patron, Big Tim Sullivan—saw to it that much of it found its way into the pockets of the desperately poor inhabitants of his Lower East Side kingdom. He was no Robin Hood, and the Lower East Side was emphatically no Sherwood Forest, but his acts of kindness and generosity; his love of children and animals; the loyalty and affection he inspired, even in some of his rivals; the testimonials to his character from those—like the officers of the 106th Infantry, Charley Jones, and Morris Pockett—who had no vested interest to protect; and above all, Monk’s courage and dedication to others in the furnace of the battlefields of the Western Front argued of a far more complex character than the brutal, mindless thug his detractors described. He had lived most of his life in the shadows of the underworld, but he emerged into the light and by his actions redeemed some, perhaps all, of the many crimes he had committed. In a life characterized by venality, he also proved himself capable of selflessness and altruism, even risking his life to save others, the most Christian act a man can perform.
An enigma throughout his life, Monk Eastman went to his grave leaving a score of unanswered questions behind him. When he spoke for the record in court, or in police or newspaper interviews, he almost invariably lied. He left not a single word written in his own hand, made no deathbed confession, and left no last will and testament. The true extent of the reformation of “Citizen Eastman”; the ultimate fate of his wives, his children, his property, and the fortune he made from his crimes; and the real reasons for his killing on that cold December night remain unknown to this day.