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The Brief Reign of ‘Kid Dropper,’ the Lower East Side Gang Leader

At 28, Nathan Kaplan was a legend. Four years later, he was dead.

Allan Levine
December 14, 2023

Tablet Magazine

Tablet Magazine

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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“Kaplan had a way of convincing those who were to appear against him that it was in their best interests to forgo their testimony.”
New York Times, Aug. 29, 1923

While some Lower East Side Jewish gangsters like Dopey Benny Fein and Waxey Gordon managed to make it into their 50s and 60s, many more like Big Jack Zelig and Jacob “Little Augie” Orgen died young. So, too, did “The Dropper,” also known as “Kid Dropper” or “Jack the Dropper,” all aliases of Nathan Kaplan (originally Caplin), who preferred the first name Jack. For about four years, from 1919 until he was murdered at the age of 32 in front of the Essex Market Police Court on the East Side on Aug. 28, 1923, Kaplan was the neighborhood’s reigning gangster leader.

He was born on Aug. 3, 1891, one of seven sons of Joseph Caplin, a Russian Jewish immigrant, who resided with his family in an East Side tenement. Nathan’s mother died when he was still young, contributing to his gradual drift into juvenile delinquency. His first arrest was in early February 1908, when he was 17 years old, on a theft charge; he was given a suspended sentence. A year later, Kaplan was in court for concealing a weapon, an offense for which the judge again gave him a suspended sentence. He was already preying on small merchants on the East Side and stealing pennies from children on the streets.

By this time, Kaplan had adopted his “Kid Dropper” persona. There are two stories about how he got the nickname. The generally accepted version is that at a young age, Kaplan perfected a scam known as the “drop swindle.” He surreptitiously dropped a wallet filled with counterfeit money near a stranger. Then he picked it up as the victim, or “mark,” was also retrieving it. As they both claimed the wallet, he told the victim that he was in a rush and agreed to give the wallet to the stranger in exchange for a fee and assured the victim—assuming this person did not plan to keep the money—that he could obtain a reward by returning the wallet to its rightful owner. Or, according to The New York Times, the story of the nickname was simpler. “He gained the title of ‘Kid Dropper,’” the newspaper explained at the time of his death, “when as a young messenger in Wall Street he knocked out those who went counter to his wishes,” usually with a blackjack. Given Kaplan’s thick, burly build and frequent thuggish demeanor, the second version seems more likely. Either way, the legend of “The Dropper” was born among East Side gangsters.

Unlike many young Jewish boys who joined an East Side-based gang, Kaplan came under the tutelage of Paul Kelly (Paulo Antonio Vaccarelli), a former boxer, who in the first decade of the 1900s, while he was in his mid-20s, headed a powerful Five Points gang. Like Kelly, the members of the gang were primarily Italian, but there were a few Jewish boys such as Kaplan among the group as well. This was despite the fact that Kelly’s chief nemesis was Monk Eastman, then the leader of the East Side Jewish gang.

Another member of the Kelly gang in these years was Giovanni Mistretta, or John Mestrett, as he also known; he preferred the aliases John Wheiler and “Johnny Spanish” (he had an Italian father and Spanish mother). A bitter rivalry later developed between Kid Dropper and Johnny Spanish. For young thugs like them, there was an aura about Kelly that was hard to resist. As crime writer Jay Robert Nash notes, Kelly was “cunning and clever … [and] an inventive criminal, the first to conceive of crime as an organized business in the U.S.” Kelly also mentored such notorious gangsters as Al Capone and Johnny Torrio. He owned brothels and fostered close ties to Tammany Hall, the New York Democratic Party’s political machine, getting rich in the process through extortion rackets and other corrupt practices—all sanctioned and protected by local political bosses.

With Kelly’s decline—two of his former men tried to kill him—and eventual retirement, Kid Dropper formed his own small gang and formed an alliance, if temporarily, with Johnny Spanish. But the two had a falling out over a 19-year-old woman, Beatrice Kastant or Konsant (she was also identified in a few news stories as Beatrice Kaplan, though she was not related to Kid Dropper), with whom Spanish fell in love. In one altercation, Dropper almost killed Spanish in a knife fight. Spanish also was embroiled in a feud with another gang leader, Jacob Siegel, known as Kid Jigger, who operated gambling parlors on the East Side. In May 1910, Jigger and Spanish got into a shootout on Forsyth Street during which 13-year-old Rachel Rooten (or Rooton), an innocent bystander, was shot and later died from her wounds. To evade the police, Spanish left New York for several months.

Upon his return in September, Spanish suspected that his girlfriend, Beatrice, may have been intimate with Kid Dropper, which made him explode with anger—or so it was alleged. What precisely happened next and in what chronological order is not entirely clear since newspaper stories of these events differ. The most likely scenario (also suggested by crime writer Daniel Waugh, who has extensively researched Spanish’s life) is that early in the evening of Sept. 23, 1910, Spanish went after Kid Dropper, shooting him in the neck while he was walking near the corner of Jefferson and Monroe streets. He fell to the sidewalk, yet survived. As described by the New York Daily Tribune, “the bullet had passed out through his mouth, carrying away four of his upper teeth.” He muttered to the police officer who attended to him that the shooter was “Johnny Spanish.”

Later that evening, Spanish took Beatrice to Maspeth in Queens, which in those days was still being developed, to attend a “frolic” (a party in a rural area) of a Brownsville gang. As they were walking down Grand Avenue, he grabbed her two wrists, pulled a pistol from his pocket, shot her in the abdomen, and left her lying on the sidewalk. The shooting was witnessed by an 11-year-old boy. By most accounts, Beatrice did not die from her wounds. When asked by the police to identify the shooter, she refused to say it was Spanish who had shot her. The tale of this crime was further embellished by investigative journalist Alfred Henry Lewis in a feature article (in which Beatrice for some reason is called Alma) published in The Sun on Oct. 6, 1912, with the additional detail that Beatrice was pregnant, presumably with Kid Dropper’s child, which was the reason Johnny Spanish had aimed his pistol at her stomach. The baby, he added, survived, but was born missing two fingers supposedly shot off by Spanish’s gun. Herbert Asbury later gave the story of the baby further credibility by including it in his book, The Gangs of New York. There are, however, no references to her being pregnant in the newspaper accounts of 1910 or 1911.

Spanish hid out in Detroit and then Queens, where his family resided for several months before he was apprehended by the police. He was indicted for the robbery of a saloon—though not for killing Rachel Rooten or shooting Beatrice Konstant because of a lack of evidence. He confessed to the robbery and received a seven-to-10-year sentence in Sing Sing. Meanwhile, two months later, Kid Dropper also had his time in court after he was tried for robbing a boarding house. After he and two accomplices had taken money and valuables from the occupants of the house at gun point, Dropper had hit a woman in the head with the butt of his revolver because he believed she was trying to summon outside assistance. Like his rival Spanish, Dropper was given a seven-year sentence in Sing Sing.

During his stay in prison, Kid Dropper became embroiled in a massive scandal involving Sing Sing’s warden, Thomas Osborne. A humanitarian, Osborne, soon after his appointment in December 1914, introduced major reforms and self-help programs for prisoners. These changes were vehemently opposed by Williams Cummins, a former Manhattan banker who had been imprisoned for larceny. Cummins was the corrupt “king” of the prison and did not want to lose his various entitlements. To this end, Cummins launched a smear campaign against Osborne that remarkably led to a grand jury indictment for perjury and neglect of duty—including allegedly allowing “immoral” activities to take place in the prison. Dropper had given testimony to the grand jury supporting Osborne and claimed that Cummins had hired him to assault another prisoner. As payback, another inmate told the grand jury the (false) story that Dropper acted as Osborne’s “house boy,” that he “wore the warden’s clothes and smoked the warden’s cigars,” and was on “intimate terms” with Osborne. Ultimately, the charges against Osborne were dismissed and he served as warden at Sing Sing until 1916.

By late 1917, both Kid Dropper and Johnny Spanish were out of prison and back on the East Side. With Dopey Benny Fein’s retirement as a “strong-arm” for unions and Louis “Lepke” Buchalter and his partner Jacob “Gurrah” Shapiro not yet the chief labor racketeers, Dropper and Spanish vied for work from garment factory owners as well as unions. While the two gangsters agreed “to peaceably co-exist in the underworld,” as Daniel Waugh puts it, the animosity between them persisted as the competition for business intensified.

Late in the afternoon of July 29, 1919, Dropper and three of his men—Herman “Hymie” Kalman (or Kellman), William “Billy the Kid” Lustig, and Nathan Gordon—confronted Spanish as he was about to enter a restaurant on Second Avenue close to East First Street where he was meeting his wife and his driver, Philip Rotkin. According to witnesses, words were exchanged and then one of the well-dressed men, either Kid Dropper or Kalman, pulled out a gun and fired two shots into Spanish’s chest. Hearing the gunfire, his wife and Rotkin ran outside and found Spanish, 30 years old, lying on the sidewalk. He died a short time later at Bellevue Hospital. By the evening, Kalman and Lustig had been arrested for the murder and within a few weeks, Dropper and Gordon, another of his men, who was believed to have been present at the time of the shooting, were all in custody. In late August, they were all indicted for first-degree murder. Yet, as it was with so many charges brought against Dropper, the District Attorney’s Office did not have sufficient evidence to proceed to trial.

Kid Dropper had his moment in the gangster sun, at least for a few years.

Johnny’s brother Joey Weiler, however, was intent on revenge. He began stalking Kid Dropper, biding his time until he was ready to act. That happened on the evening of Dec. 3, 1919, outside Dropper’s home on Madison Street—except Joey made a mistake. He saw who he believed was Kid Dropper walking with a young woman. He approached the pair and shot wildly. He had fired at Dropper’s brother Adolph Caplin and his friend, 18-year-old Martha Janoff. The shots missed Adolph, but struck Martha in the abdomen. As Joey pursued Adolph, a patrolman appeared and apprehended Joey. Martha was taken to the hospital and though her wounds were serious, she (presumably) recovered. Joey was charged with felonious assault and illegal possession of a revolver.

With the death of his rival Johnny Spanish, Kid Dropper had his moment in the gangster sun, at least for a few years. He made lots of money “slugging” for both management and unions, and got married to a young woman named Irene, though he could not stay out of legal trouble entirely. In 1920, he was incarcerated for short stints in Blackwell’s Island penitentiary and in the spring of 1922 faced charges for conspiracy and felonious assault; both were dismissed.

The summer of 1923 proved to be more problematic and fateful. Kid Dropper faced competition for “strong-arming” from Jacob “Little Augie” Orgen, who had been released from prison after serving several years on a robbery conviction. Once he was out, Orgen immediately regrouped his gang, infiltrated labor organizations, and became Dropper’s new chief enemy. Violence between the two was inevitable. On the evening of Aug. 1, 1923, a shootout on Essex Street on the East Side broke out between William Weiss, allied with Orgen, who was walking with his girlfriend, Gussie Schwartz, 25, and at least three of Dropper’s men who fired at the two from their touring car. Dropper himself may have been in the automobile. In the melee, several bystanders were hit and a bullet missed hitting (and likely killing) a newborn baby by inches. Weiss and Schwartz eventually recovered. A few weeks later, the police arrested Dropper and 15 of his men in the Putnam Building on Broadway after they received a tip that Dropper and his gang were planning how to intimidate workers in an impending theater strike.

Jacob ‘Little Augie’ Orgen, who likely ordered Kaplan's murder
Jacob ‘Little Augie’ Orgen, who likely ordered Kaplan’s murder

Tablet Magazine

On Aug. 28, Kid Dropper was at the Essex Market Court House, where he and his men were arraigned on charges related to the Aug. 1 shootout. However, the judge was forced to release Dropper after a witness recanted and now said that Dropper had not been in the car firing his gun at Weiss and Schwartz. As soon as the magistrate dismissed the charges against Dropper, the police took him into custody again for violating the Sullivan law for possession of a dangerous weapon.

With Detective Sergeant Jesse Joseph by his side and Acting Captain Cornelius Willemse, wearing a straw hat, nearby, Kid Dropper emerged from the courthouse with his wife, Irene. The police intended to transport Dropper uptown to another courthouse by taxi. A small crowd greeted them. “Jack, you’ve beaten all other cases,” Irene told him, using his preferred first name, “and you’ll beat this one uptown.” She hugged him around the neck and kissed him. Dropper crawled into the taxi, which had its motor running, and Joseph followed. As the detective did so, a small, thin man pushed his way through the crowd, ran toward the taxi, took out a pistol, and fired three times through the rear window of the car. The first shot hit Dropper in the back of his head, the second one hit the cab driver behind his ear, and the third pierced Willemse’s hat. Irene reached Dropper first and pushed the shooter away, scratching his face. The man pushed Irene to the side and fired several more times. More police officers arrived and subdued and disarmed the shooter. As an ambulance pulled up, Dropper muttered to Detective Joseph, “Jesse, they’ve got me,” before falling unconscious. Nathan Kaplan, the infamous Kid Dropper, was dead by the time the ambulance reached the hospital; he was 32.

The shooter was Louis Kerzner, alias Louis Cohen, a 19-year-old with hopes of becoming a full-fledged member of Little Augie’s gang. He was, as The New York Times later put it in a feature article on Sept. 9, “‘gang-struck’ as other youths are stage-struck.” Orgen did not believe Kerzner had what it took and instead used him as an errand boy. When first questioned by the police, Kerzner claimed he acted independently and that he shot Dropper because he feared Dropper would kill him.

“The Dropper has been hounding me for a long time,” Kerzner said. “Two weeks ago, he wanted to shake me down for $500 and when I told him I didn’t have it he said he would have me bumped off. A couple of weeks ago Louis Schwartzman, one of my best friends, was killed on the Dropper’s order. A few days ago on Essex Street, the Dropper and two of his men drew up to the curb where I was standing. They intended to get me then, but I ran away. I knew this sort of thing couldn’t continue so I went down to the court and waited for him to come out.”

The DA’s office and the police were skeptical of Kerzner’s tale and were convinced that Little Augie had instructed Kerzner to kill Kid Dropper, possibly with the promise that if he did so, Orgen would permit him to become a gang member. The murder, it was believed, was revenge for the previous attack on William Weiss and to rid Orgen of his nemesis forever. While this theory made sense, the police found no evidence to support it and the case against Orgen and another of his men who had been charged in the murder conspiracy, was dismissed.

Kerzner was convicted of murdering Kaplan. Because there was some doubt about what had transpired, he was given a 15-year prison sentence, rather than being sent to the electric chair. He was released in February 1937. About two years later, he and a friend were attacked on the street and both were shot dead. Kerzner was 35 years old; he had outlived Jacob “Little Augie” Orgen, who was murdered in mid-October 1927 at the age of 34, most likely on the orders of Louis “Lepke” Buchalter and Jacob “Gurrah” Shapiro over a financial dispute about the strong-arm business.

More than 2,000 people (and about 50 police detectives) attended Kid Dropper’s funeral and those closest to him, like his brothers and wife, praised him for being an “honorable son” and loving and loyal husband. “Why did they kill that good man?” Irene screamed. But Louis Kerzner was right to fear Dropper: He epitomized the viciousness of East Side gangsters, and Kerzner’s idolization of Jacob Orgen was equally misguided. Kerzner was “incapable of seeing the obvious,” added the Times on Sept. 9, “the gang is no longer a corps to which even a remote valor attaches.” There was nothing romantic or glamorous about the likes of Little Augie or Kid Dropper.

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