"Kid Dropper" Nathan Caplin or Kaplan [Caplan] (1891 - August 28, 1923), also known as Jack the Dropper, was an American gangster controlling labor racketeering and extortion in New York City during the post-World War I period into the early years of Prohibition in the early 1920s. One of seven children, Kaplan was born in New York's Lower East Side around 1891. Kaplan began committing petty theft at an early age and later becoming a skilled sneak thief and pushcart extortionist, later becoming known for the "drop swindle". Around 1910, Kaplan had formed his own gang (associated with the Five Points Gang) briefly feuding with rival gang member Johnny Spanish until his arrest the following year for robbery and sentenced to seven years in Sing Sing prison. Upon his release in 1918 Kaplan became involved in "labor slugging", providing muscle to either side in the strikes common in New York in that era. Kaplan quickly filled the void left by "Dopey" Benny Fein and Joe "The Greaser" Rosenzweig in the aftermath of the internecine battles between gangsters, organizing former Five Points members, including Johnny Spanish. Kaplan and Spanish, who had previously reconciled from an argument over a woman from their days in the Five Points Gang, soon began feuding again as Spanish split from Kaplan's gang. A violent war between the two soon began; fighting, particularly in the garment district, continued until Johnny Spanish was killed while leaving a Manhattan restaurant by three men, most likely including Kaplan, on July 29, 1919. After Johnny Spanish's death Kaplan controlled all of labor slugging operations in New York. While Kaplan worked primarily for labor unions, he occasionally provided services for employers. By the beginning of 1923, however, Kaplan began to face increasing competition from rival newcomers Jacob "Little Augie" Orgen, Jack "Legs" Diamond, Louis "Lepke" Buchalter, and Gurrah Shapiro. Kaplan and Orgen soon began fighting over protection of wet wash laundry workers in violent shootouts around New York. On August 28,1923, Kaplan was arrested for carrying a concealed weapon and arraigned at Essex Market Court. News of the arrest attracted a large crowd of reporters and bystanders. As Kaplan was being transferred to another court, led by a police escort, he was shot and killed by Orgen gunman Louis Kerzner just after he entered a police car. Orgen gained control of Kaplan's operations until his death in 1927, possibly by Buchalter and Shapiro.
Further reading
- Sifakis, Carl, The Encyclopedia of American Crime: Second Edition Vol. II (K-Z), Facts On File Inc., New York, 2001.
