Nathan Caplin, aka Kaplan and "Kid Dropper," was arrested for robbery in 1911 while a member of the Five Pointers gang and did seven years in Sing Sing.

Kaplan (as he was more widely known) had gotten the "Kid Dropper" tag because early in his criminal career he practiced the "dropped wallet" scam.

One of the many variations of the con scheme, that still is pulled even these days, involves a billfold of mostly counterfeit money being dropped near the intended victim ("the mark") who reaches for it only to see a stranger (the con artist) pick it up first. The stranger, supposedly in a hurry to keep an appointment elsewhere, offers to give up the wallet for some financial consideration. Only after the victim provides that consideration from his own wallet is the victim given the dropped billfold. By the time that the counterfeit nature of the dropped wallet's bills is detected, the con artist is gone from the scene with the mark's real money.

After prison release in 1918, Kaplan got into a racket known as "labor slugging." That involved supplying "goons" or "sluggers" either to unions or to managements during the violent labor disputes of the era. In these activities, Kid Dropper associated with a former Five Pointer member with whom he had a rocky relationship, Johnny Spanish. When the latter was gunned down July 29, 1919, as he left a restaurant in the East Village section of Manhattan, Kaplan was suspected and arrested but, because of lack of evidence, never prosecuted.

Johnny Spanish's death left Kaplan in virtual control of New York labor slugging. But in 1923 he began encountering competition from some "newcomers" that included Jacob "Little Augie" Orgen, Jack "Legs" Diamond, Louis "Lepke" Buchalter, and Jacob "Gurrah" Shapiro. The Kaplan-Orgen rivalry over laundry workers triggered shootouts.

On Aug. 28,1923. Police Captain Cornelius W. Willemse, a top gangbuster cop of the era, was overseeing the arraignment of Kaplan on a gun charge. Aware a "contract" had been given out on Kid Dropper, the captain posted heavy police guard at the Essex Market Courthouse and personally accompanied Kaplan there in a taxi.

Willemse warned Kaplan to get out of town because rivals were gunning for him. As the two seated themselves in the back in the cab for the ride to Penn Station, inconspicuous 17-year-old Louis Kerzner aka Kushner aka Cohen -- whose small size made him look even younger than his actual age -- walked up behind the taxi and pumped five shots through the rear window, killing Kaplan. One bullet went through Willemse's hat.

Cohen, caught at the scene, later claimed Little Augie's gang got him high on liquor and drugs and persauded him he'd be a big man in town if he knocked off Kaplan. With future mayor James J. Walker as his lawyer, the boy avoided the chair, was sentenced to 15 years and was paroled in 1937. But on Jan. 28,1939 Cohen himself was shot on a Manhattan Street.

Image of Nathan "Kid Dropper" Caplin aka Kaplan from promo card for Ron Arons' lecture The Jews of Sing Sing lecture at Temple

NYCHS webmaster notes beneath image.

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NYCHS board member Judy Berdy, who is administrator at the Skirball Center for Adult Jewish Learning at Temple Emanu-El, suggested NYCHS website readers might be interested in the subject matter of Ron Arons' April 25 lecture sponsored by the Bernard Museum of Judaica & Stettenheim Library at Temple Emanu-El.

Judy also is president of the Roosevelt Island Historical Society.

This presentation is a follow-up on her suggestion.

Elizabeth F. Stabler, Temple Emanu-El librarian, provided the photo postcard announcing the lecture.

Ron Arons, who designed the postcard, took the photos of the guard tower and Cell Block A. He credits the "illustrations of the various tortures" and the electric chair photo to "the Ossining Community Center."

The format for this web presentation was designed by the NYCHS webmaster whose own research notes appear on the left below the image.