"Kid Dropper" Nathan Caplin or Kaplan (August 3, 1891 – August 28, 1923), also known as Jack the Dropper, was an American gangster who controlled 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.
[2] 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.
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.
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.
[4] Orgen gained control of Kaplan's operations until his own violent death in October 1927, possibly at the hands of Buchalter and Shapiro.