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The Gangster Who Defended the Unions—With a Lead Pipe

‘My heart lay with the workers,’ said ‘Dopey Benny’ Fein, expert organizer and ‘shtarker’ of the Lower East Side

Allan Levine
June 15, 2023
Original image: Public Domain
Benjamin ‘Dopey Benny’ Fein, 1942Original image: Public Domain
Original image: Public Domain
Benjamin ‘Dopey Benny’ Fein, 1942Original image: Public Domain
Editor’s note: Chronicled and mythologized in scholarly and popular history books, novels, films, and plays, New York’s Lower East Side in the late 19th and early 20th centuries was overcrowded, and teeming with peddlers, tailors, sweatshops, and barely livable tenement houses. By 1910, an estimated 540,000 Jews resided within the neighborhood’s 1.5 square miles. The poverty, hardships, and daily struggle to survive drove some Jewish immigrants to seek other ways to make a living, even get rich. Hence, the Lower East Side also had a vast collection of crooks, pimps, prostitutes, thieves, pickpockets, gangsters, fraudsters, forgers, arsonists, and hoodlums. Offered here is one of an ongoing series of portraits of some of these nefarious characters, who also left their mark on the Lower East Side’s historical legacy. 
This article is part of The Dark Side of the Lower East Side.
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“Benjamin Fein has come into the public view as the organizer of the gangster business who placed it on an economical basis and while making it profitable for himself provided reasonably steady work for his employees … Mr. Fein, otherwise known as Dopey Benny, whose confession has been so helpful to the police, is no innovator in his art, but he will be remembered as an expert organizer.”
—New York Times,
May 16, 1915

If ever there was the archetypal Jewish shtarker, or gangster-thug, in the annals of the Lower East Side, it was Benjamin Fein, more notoriously known as “Dopey Benny.” He was no drug or dope fiend, as his street monicker suggested. An adenoidal and nasal problem that made his eyelids heavy was the reason his fellow gang members anointed him with his nickname.

The Dope, as he was also called in the press, was clever and cunning. While only in his mid-20s, he took advantage of the so-called “business” opportunity that presented itself, providing “muscle” and “strong-arming” to struggling garment unions then at the mercy of manufacturers, who hired their own thugs to terrorize union leaders and striking workers. Monk Eastman and Big Jack Zelig, Benny’s predecessors as head of the East Side gang, initiated such shtarker (or starker in newspaper stories) work for the garment industry, but it was Dopey Benny who was a true pioneer of labor racketeering in Manhattan. He was indeed the “expert organizer,” as The New York Times designated him, who made assaulting and maiming someone and wrecking shops and factories profitable commercial ventures governed by set fees and contracts drawn up by lawyers.

Often nasty and brutal, Benny had no qualms about beating someone, clipping ears, or breaking kneecaps and arms—or ordering his men to do so—if that was what the job or situation demanded. On one occasion, he was hired by a union leader to punish a “forelady” for being too cozy with a factory owner. Benny was instructed to throw this woman down the cellar stairs. At first, he was reluctant to hurt the woman. Yet, when the union official told him that he would no longer hire him for future jobs if he did not do what was required, Benny acquiesced. “We followed the woman until she was passing a saloon with an open cellar door,” he later recalled. “We threw her down the open cellar and got away. She screamed and a lot of people came who took her to a drug store. I got $50 for that job.”

There was nothing unusual or disturbing in Benny’s childhood that set him on his nefarious career path. Quite the opposite, in fact. He was born on July 20, 1887, into a typical East Side Jewish immigrant family (the family’s surname was originally Feinschneider). His father, Jacob, was a tailor and he had four sisters. At a young age, however, like other Jewish children of his generation who grew up in the East Side, Benny got into trouble. He started stealing packages from delivery carts and became a skilled pickpocket, so much so that while he was still a teenager, he trained other boys to be thieves.

In early October 1905, an East Side public school principal launched a complaint with the police that Dopey Benny, as he was already known, was seen walking in the vicinity of the school recruiting boys to join what the Times called his “criminal academy.” The principal said that many of his students were seduced by Benny’s promises of money and good times. Soon after, the police arrested Benny on charges that he had robbed one man and assaulted another.

Before he was 20 years old, Benny had been sentenced to two terms at the Workhouse prison (for minor offenses) on Blackwell’s Island (now Roosevelt Island); sent to the Elmira Reformatory on a grand larceny conviction; and arrested several times for assault and disorderly conduct. At some point, he joined Monk Eastman’s gang and met Big Jack Zelig, among other East Side gangsters who mentored him. In late October 1908, Benny’s legal troubles got worse: He was convicted of burglary and was incarcerated for three-and-a-half years in Sing Sing prison. There were to be many more arrests for him in the future and he was to spend more time locked up in prison. But such legal consequences did not deter his criminal enterprises.

Benny was released from Sing Sing in mid-1912. A few months later, Zelig was murdered while he was on a trolley car. There was a brief power struggle between Benny and Joe “the Greaser” Rosenzweig for leadership of the Zelig gang, which Benny won without much difficulty.

Benny’s rise to power coincided with unrest in the New York garment industry. Despite the establishment of unions like the International Ladies’ Garment Workers’ Union (ILGWU) and the United Hebrew Trades (UHT)—which by 1910 had 106 unions in its organization that represented approximately 150,000 men and women—the fight for higher wages, better working conditions, and collective bargaining rarely stopped. There were long, bitter, and often violent strikes. Though there were negotiated agreements—like the “Protocol of Peace” in 1910 that ended the walkout of about 65,000 cloakmakers—management did not always honor such deals, routinely used strikebreakers, and hired thugs to harass and beat workers on the picket lines. In such confrontations, the police tended to side with the factory owners.

It only made sense—or so it seemed—for the unions to fight fire with fire and hire their own thugs to protect their members and mete out punishment to those who challenged or opposed them. While Monk Eastman and Jack Zelig offered their shtarker services to both management and unions, Benny decided that he and his men were to become the guardians of the unions and the beleaguered Jewish working men and women toiling in factories and sweatshops. He later claimed that “my heart lay with the workers,” and that he had even twice turned down payments of $15,000 (about $450,000 today) from garment industry owners to end his work for the unions, yet he refused both times.

Whether he was being genuine is hard to say. He was well paid by the unions and would not have wanted to jeopardize that profitable relationship. Assistant District Attorney Lucien Breckenridge, who interviewed Benny at length in 1914-15, believed he was being sincere in his championing of the workers. “The man really had a conviction,” said Breckenridge, “that he was helping along in his own way a cause in which he believed.”

Whatever Benny’s true motivations, once the unions enlisted his gang’s services, their battle with the owners became even more violent. It was a dicey arrangement, which served to taint union leaders, directly link them to criminal actions that they could not always control, and embroil them in serious problems with New York justice officials.

The gangsters were remunerated in two ways, though all the money was filtered through Benny, who paid his men about $7.50 a day at a time when a garment worker barely made $2 (perhaps as much as $2.50) a day. Benny, himself, became wealthy. He estimated that he was making $10,000 a year (about $300,000 today), a sizable fortune in 1914. For several years, Benny received a weekly salary as high as $40 from UHT (and $25 if he was in jail). This was in addition to his extra fees for specific services, which were all itemized in his contract. Raiding and wrecking a small manufacturing shop cost $150 and for a larger one, $600. For shooting someone in the arm or leg or cutting part of an ear off, the fee was anywhere from $60 to $100, depending on the severity of the damage inflicted. It cost $200 to throw a foreman down an elevator shaft or break his arm or thumb, and the same price for a “complete knock-out” of any working man. For factories that had primarily female employees, Benny enlisted a team of women gangsters armed with sharp hatpins and umbrellas weighted down with lead slugs so that the bosses and seamstresses would get the union’s “message.”

The gangsters’ favorite weapon was a sawed-off lead pipe covered in a newspaper. Benny convened his own tribunal in which he acted as judge to determine the guilt and punishment of a worker who had disobeyed union officials by not joining a picket line or, worse, was a strikebreaker at a different factory from the one where they were employed. Once Benny had delivered his judgment, no appeals were allowed. Those found guilty had their thumbs or arms broken or their ears slashed.

To bring a semblance of order to the business, Benny sought out alliances with other gangs. He devised a system where each gang only accepted contracts in their own designated district or neighborhood. So, if, for instance, Benny, was offered a contract to go after someone on the Lower West Side (Tribeca), he turned over the job to the Hudson Duster gang, and the Hudson Dusters reciprocated by passing on any gang work offered to them in the East Side to Benny, where he was the boss. The system worked reasonably well except several gangs, most notably, the one in Five Points controlled by Jack Sirocco and Chick Tricker, longtime and bitter rivals of the Jewish East Side gang, refused to cooperate or take orders from Benny.

The Sirocco and Tricker gang often acted as thugs for employers, which put them on the opposite side from Benny and his men. In 1913 and 1914, the violent battles between the two gangs intensified and on more than one occasion, as the gangs shot wildly at each other seeking revenge for one action or another, innocent bystanders were injured and killed. The worst altercation occurred early in January 1914 when Benny and his men ambushed a group of Sirocco-Tricker men near the Arlington Dance Hall at St. Marks Place. The attack was retaliation for a recent shooting at Benny and a few of his men by the Five Points gangsters in front of Madison Square Garden. No one died at that earlier shootout. But this time, Frederick Strauss, a 65-year-old clerk at the city court with a wife and children, happened to be walking by the dance hall when the gunfire started and he was killed.

Once Benny had delivered his judgment, no appeals were allowed. Those found guilty had their thumbs or arms broken or their ears slashed.

Strauss’ death shocked the city and the district attorney and the police were determined to arrest those responsible. Within a few days, Benny and several of his men were taken into custody. Yet, they were soon released because officials did not have sufficient evidence to indict them. Benny claimed that his arrest “was part of a systematic persecution of him.”

Benny’s legal troubles did not end there. Five months earlier, in August 1913, he had had an altercation with an NYPD sergeant named Patrick Sheridan, who had accused Benny of loitering in front of a Turkish bath. Sheridan later said he was responding to a complaint made by the bath’s owner, but the owner denied that he had asked the police for assistance. In any event, a fight broke out between Sheridan and Benny. Depending which version of this story you believe either Benny grabbed Sheridan’s nightstick and beat him with it, or in the more likely scenario—one related by Abe Shoenfeld, the chief investigator for the New York Kehilla’s Bureau of Social Morals—Sheridan struck Benny in the face for no reason. Benny hit Sheridan back. The officer then took out his nightstick and whacked Benny on the head with it. Other police officers soon arrived and when Benny resisted arrest, the officers used blackjacks to beat him badly into submission.

Despite Benny’s obvious injuries at the hands of the police, he was charged with felonious assault (or assault with a deadly weapon). At his trial held at the end of January 1914, he was found guilty and sentenced to a five-year prison term. This time, justice, at least from Benny’s point of view, prevailed. His lawyers appealed the sentence and in late May 1914, the Appellate Court reversed the conviction and ordered a new trial. The judge ruled that Benny had struck Sheridan, but that the policeman was not hurt severely enough to warrant the gangster being charged with felonious assault. He was released from prison on bail and subsequently exonerated.

While awaiting a new trial in the Sheridan case, he found himself in legal jeopardy yet again. This time, he was arrested for extorting and threatening butcher Benjamin Solomonowitz, an organizer for the Butcher’s Union. Benny assumed that the UHT would pay his $7,500 bail (later raised to $10,000), but no financial assistance was forthcoming. Angry and feeling betrayed, he made a deal with the Manhattan district attorney, Charles Perkins, and confessed to his many sins, including exposing his shtarker work for the Jewish unions. In exchange for dropping the extortion charges, Benny testified before a grand jury in February 1915 and then in mid-May he spoke to the press. The police and DA’s office also made much of his testimony available to the public. Featured in the newspapers, it was a sensational tale of corruption and the inner workings of the gangster business going back to the days of Monk Eastman. As evidence of transactions with the unions, Benny provided the DA with his diary containing lists of names and amounts paid to him by labor leaders who hired him and his men for various jobs.

There was a serious fallout from Benny’s grand jury testimony. Twenty-three union leaders, mostly from the UHT and Cloak and Shirtmakers’ Union, were arrested as were 11 gangsters for their strong-arm work. The union officials were accused of hiring thugs to terrorize employers and they and the gangsters were charged with assault, extortion, and rioting. Seven union officials were also charged with conspiring in the murder of Herman Liebowitz, a cloakmaker and union member, who during a major strike in 1910, had worked in a nonunion shop outside of the city in order to provide for his family.

Abraham Shiplacoff, the secretary of the UHT—among other Jewish labor leaders and pro-union newspaper editors such as Abraham Cahan of the Forward—denounced the DA for targeting Jewish union officials. While Shiplacoff declared that Benny was “a terrorist, a low gunman and a scoundrel,” most Jewish union officials and newspaper editors avoided commenting on the connection between the unions and the gangsters. Because, as historian Jenna Weismann Joselit points out, “to many Jews, they were obviously not the revelations they were touted to be.” Despite the hyperbole around the indictments, Perkins and his staff, in the end, were unsuccessful in securing a conviction in the Liebowitz murder trial and other indictments against the union leaders and the gangsters were dismissed by Perkins’ successor, Edward Swann.

In January 1916, Benny spent two months in jail for assaulting a strikebreaker. By the end of the year, having been accused again of involvement in killing of Frederick Strauss in January 1914 in testimony given to the DA by his old gangster colleague, Joe “the Greaser” Rosenzweig, then serving a 10-year sentence in Sing Sing, Benny decided to go straight—at least temporarily. He purchased his own garment manufacturing business and in 1917 married Gertrude Lorber. By 1929, they had a daughter and two sons.

Benny (presumably) stayed out of trouble until the summer of 1931 when he and two associates appeared in court accused of felonious assault for throwing acid on a businessman named Mortimer Kahn. There were no legal consequences for this alleged action, however. A decade later, Benny, then 55 years old, was arrested again along with veteran gangster Abe Cohen, 57, and several other men on a stolen goods charge and involvement with the robbery of a large garment shipment. In late October 1941, the two men were found guilty of “criminally concealing and withholding stolen and wrongfully acquired property” and received lengthy jail sentences. Yet, once more, Benny was lucky. He and Cohen only spent about two years in prison. In 1944, an appeal judgment granted them a new trial and they were both acquitted.

Thereafter Dopey Benny’s gangster days finally ended for good. He died from cancer on July 23, 1962, a few days after his 75th birthday. No doubt, he had spent his last years regaling his grandchildren with wild stories about his days as a shtarker and East Side gangster boss, tales of crime and mayhem that the youngsters probably had a hard time believing.

Historian and writer Allan Levine’s most recent book is Details Are Unprintable: Wayne Lonergan and the Sensational Café Society Murder.