Nathan Kaplan
| Kid Dropper | |
|---|---|
| Born |
Nathan Caplin August 3, 1891 Lower East Side, New York, United States |
| Died | August 28, 1923 (aged 32) Manhattan, New York, United States |
| Cause of death | Murdered |
| Resting place | Mount Hebron Cemetery |
| Other names | Nathan Kaplan, Nathan Caplan, Jack the Dropper |
| Occupation | Labor racketeer |
| Known for | Gang leader and underworld figure who controlled "labor slugging" in New York from 1919 to 1923. |
"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 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 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 unions, he occasionally provided services for employers.
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