"Kid Dropper" Nathan Caplin or Kaplan (August 3, 1891 – August 28, 1923), also known as Jack the Dropper, was an American
gangster controlling labor racketeering
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
on August 3, 1891. Kaplan began committing petty theft at an early age and later becoming a skilled sneak thief
and pushcart extortionist, later becoming known for his skill with the "drop swindle
". He was originally a member of the Paul Kelly
's Five Points Gang. 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
for which he was 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 those gangsters. He organized former Five Points members, including Johnny Spanish
. Another Jewish labor slugging gang led by Jacob "Little Augie" Orgen, rose steadily behind his.
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 and eventually Spanish split from Kaplan's gang, forming his own separate 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. Soon thereafter, Little Augie went to prison and his gang nearly dissolved, leaderless. After Spanish's death and Orgen's incarceration, Kaplan controlled all of labor slugging operations in New York. While Kaplan worked primarily for labor union
s, he occasionally provided services for employers.
By the beginning of 1923, however, Kaplan began to face increasing competition from rivals. Jacob "Little Augie" Orgen
had just been released from prison and had gathered back his gang. Prominent among his gang were 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. In one such altercation, Jacob Gurrah Shapiro was assaulted by Kaplan personally with his gun. Little Augie took this as an opportunity and had Shapiro go to the cops and press charges.
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 own violent death in October 1927, possibly by Buchalter and Shapiro.
* Sifakis, Carl, ''The Encyclopedia of American Crime: Second Edition Vol. II (K–Z)'', Facts On File Inc., New York, 2001.
* Downey, Patrick. ''Gangster City: History of the New York Underworld, 1900–1935''. Barricade Books, 2004.
* Goren, Arthur A., "Saints and Sinners: The underside of American Jewish History" The American Jewish Archives, 1988
Category:Murdered Jewish-American gangsters
Category:Gang members of New York City
Category:Five Points Gang
Category:People murdered in New York City
Category:Deaths by firearm in Manhattan