Nathan Kaplan & The Devil You Know

Between the years of 1890 and 1914, two million Ashkenazi Jews arrived in New York City. During the same era, twenty million Europeans of other ethnicities passed through New York’s immigration facility on Ellis Island. Upon leaving the island, finding adequate housing became the first challenge encountered by most of the new arrivals. The fortunate ones were the men, women, and children who were met by an established relative or friend who was able to provide temporary housing. All others had to use their wits, instincts, and whatever little money they possessed to find a place to live. While searching for suitable housing, they needed to steer clear of the con artists, crooks, and thugs who preyed on gullible newcomers.


For the new immigrants, the old saying, “Better than the devil you know than the devil you don’t know” often proved to be poor advice. Most criminals knew preying on people of their own ethnic background would be less risky than targeting folks of a different culture. Unfortunately, unwary Jews were fleeced by Yiddish-speaking hoodlums, unsuspecting Irish families were robbed by con-men speaking with thick Irish brogues. And sadly, the same scenario of thievery repeated itself with the Italians, Scandinavians, Germans and other immigrants.


At the beginning of the 1900s, segregation by ethnicity was the accepted and preferred social reality in America. Language, familiar customs, and common religious beliefs were the main reasons why immigrants of similar backgrounds chose to huddle together. The lower east side of Manhattan with its crumbling tenements became the neighborhood of choice for Jewish immigrants. The Italians settled along a stretch of Mulberry Street and Irish immigrants found tenement housing in a section called “Hell’s Kitchen” on Manhattan’s west side.


Members of these ghettoized communities had one thing in common. They harbored a deep-rooted distrust of government agencies, which included law enforcement and the judicial system. The failure to trust the police meant that crimes in their communities would often go unreported. Unfortunately, when crimes in a community are not reported—criminal activities in that community are allowed to incubate and thrive.


One of the most vicious criminals to emerge from New York’s lower east side was Nathan Kaplan. Nathan was born in a Madison street tenement on August 3, 1891. His parents had emigrated from Russia in the late 1880s.


At an early age, Nathan proved to be a neighborhood nuisance. He was big for his age and often picked fights with other kids. By the time he was seven, he stopped going to school and began his life of crime by robbing merchandise from pushcart vendors. Before his eighth birthday, Nathan had acquired the nickname, “Kid Dropper.” He earned the moniker because of a scam which involved feigning to find a dropped wallet stuffed with money. The unsuspecting victim would observe Nathan picking up the wallet. Nathan would then explain that he wants to return the wallet but does not have the time to track down the owner. After suggesting that the rightful owner would surely give a large reward for the returned wallet, Nathan would then offer to hand the wallet over to the other person, if that person would hand over fifty dollars of his own money for the wallet. Most people would fall for the scam and give Nathan the fifty bucks. Then, by the time the duped victim realized that the wallet was stuffed with fake bills, Nathan would be long gone with the victim’s money.


When Nathan was twelve he formed his own gang of urchin thieves. He soon realized that extortion was more profitable than snatching dry goods and food items from pushcarts. For a price, Nathan would offer to protect local merchants and vendors from being robbed by other gangs.


By the time Nathan was eighteen, his reputation as a ruthless criminal was common knowledge amongst Jewish merchants in New York City.


On October 29, 1909, Nathan Kaplan was arrested for using a gun to threaten a local furniture merchant named Isaac Lipschitz. News of Kaplan’s arrest made the front page of New York newspapers. The following is a partial excerpt from the October 30, 1909, edition of The New York Sun:

Kid Dropper is the new East Side terror. In private life the name of the gang leader is said to be Nathan Kaplan. There is scarcely a merchant in the vicinity of Monroe, Madison, Rutgers and other neighboring streets who hasn’t heard of him.


Robberies on the East Side are frequent, but it is seldom that the police hear of them because the little merchants who are robbed are afraid. They had rather give up a few dollars some time or other than be beaten on the street or in their shops.”


Nathan had his day in court and he beat the rap. The presiding judge dismissed the charges. We’ll never know whether the judge was corrupt, or if it just happened to be Nathan’s lucky day.


For the next few years, Nathan continued to harass, rob, and intimidate members of New York’s Jewish community. Then, on January 26, 1911, Nathan Kaplan made a big mistake. He and four of his henchmen robbed a boarding house in Hell’s Kitchen. Miss Alice Lewis, the owner of the boarding house resisted and consequently received a severe beating by Nathan. The gang got away with over three hundred dollars. But, before the week was out, they were all arrested and spent the next three months awaiting trial in New York City’s notorious Tombs prison. On April 20, 1911, Judge Thomas O’Sullivan was assigned to hear the case. The trial lasted just two days, and it took less than an hour for the jury to find Nathan and his four accomplices guilty of robbery in the first degree. The five men were sent back to the Tombs to await sentencing.


On June 30, 1911, Judge Thomas O’Sullivan sentenced Nathan Kaplan and the members of his gang to a minimum of seven years and a maximum of ten in New York’s Sing-Sing prison. While serving his sentence Nathan, to no avail, brought a lawsuit against the warden of Sing-Sing prison. Nathan was released in 1918 and resumed his criminal activities with a vengeance.


While Nathan was in prison, labor unions had organized thousands of workers in New York’s expanding garment industry. Most of the workers were young uneducated women who operated sewing machines. The employers were usually industrious Jewish businessmen who had a penchant for making money.


In 1918 working conditions in the garment industry were horrendous and union leaders would often call for its members to strike for better conditions. That’s where Nathan saw new opportunities for making money. For the right price, Nathan would send his thugs to beat, harass, and threaten the strikers until they agreed to end the strike. However, Nathan played both sides. If a union leader wanted the owner of a garment factory to make a certain concession, he could pay Nathan to convince the owner to comply. Sometimes all it took was showing the factory owner a jar of sulfuric acid and implying what a cup or two would do the face of a wife or daughter.


With so much money being made in the garment industry, other gangsters often tried to get a piece of the action. Jacob “Little Augie” Orgen, who also grew up in Manhattan’s lower east side was Kaplan’s biggest threat. Little Augie’s methods were often more ruthless than Nathan’s.


On August 28, 1923, the police were tipped off that Nathan was carrying a concealed weapon. The police located Nathan and arrested him. Within an hour, all charges were dropped and Nathan was released. But, because there were rumors of a death squad waiting for him, the police decided to escort Nathan from the courthouse to an awaiting taxi. Just as he entered the car, Louis Kerzner, an associate of Little Augie, burst through the onlookers and fired several shots through the back window. Nathan was dead within minutes.


Kerzner was arrested. But with the help of attorney Jimmy Walker, Louis Kerzner received an unprecedented three-year sentence for the murder Nathan Kaplan.


As for Little Augie, he became the most powerful labor racketeer in the lucrative garment industry until October 16, 1927, when his pals Louis “Lepke” Buchalter and Jacob “Gurrah” Shapiro killed him in a drive-by shooting on the lower east side.