Nathan Kaplan was born on the Lower East Side of Manhattan in 1891. He took to the streets as a youth and soon became engaged in petty swindles, such as the “dropper” scheme. While no one was watching, he’d conveniently “drop” a wallet full of counterfeit money on the sidewalk. Then he would immediately “find” the wallet and look for a sucker, whom he told, “Lookit, I don’t have time to locate the owner. You take the wallet and find the owner. Give me half of what you think the reward money will be.” And dupes constantly did this for Kaplan, hence the nickname “Kid Dropper.”
Because of his expertise in making a buck, Dropper joined Paul Kelly’s (Paolo Vacarelli) Five Points Gang, which was quite unusual for the Jewish Dropper, since the vast majority of Kelly’s gang members were of Italian descent. Yet Dropper did not last too long with the Five Pointers. In 1911, he was arrested for robbery and sentenced to seven years in Sing Sing Prison. By the time Dropper was released in 1917, Kelly’s gang had been disbanded, and Dropper, considered a minor criminal before going to jail, fancied himself as successor to Kelly and he grabbed Kelly’s labor rackets business.
In his past life, Dropper was habitual wearer of slovenly attire, in other words, he dressed like a bum. Now as a boss, Dropper stared to dress accordingly. He threw away his normal rags and started prancing the streets in loud checkered suits, pointed shoes, shirts and ties with loud colors and outlandish designs, with a straw hat, or derby, tilted rakishly over one eye. Dropper compiled a motley crew of low-level gangsters and he called his gang, “The Rough Riders of Jack Dropper.” But Dropper soon found himself in a war for control of Kelly’s old rackets with an old foe, who had just been released from prison too.
Before his incarceration, Dropper had made a very bad enemy in fellow Five Pointer Johnny Spanish, a Spanish Jew, real name Joseph Weyler. The two men had been pals, until 1911, when Spanish had to take it on the lam for a shooting that resulted in the death of an innocent eight-year-old girl. Spanish split town for a few months and when he came back, he found Dropper had stolen his girlfriend. Spanish, who carried four guns with him at all times, proceeded to pepper his former love with multiple gunshots. Somehow the woman lived, but Spanish got seven years in prison for his actions. When he was released in 1917, Spanish took dead aim at Dropper and every illegal activity Dropper controlled. Each man had approximately three dozen shooters under their wings, and these shooters went to work, resulting in the deaths of several men on both sides. But the war ended, when Dropper got the drop on Spanish, so to speak, after he and two of his men ambushed Spanish as he exited a restaurant at 19 Second Avenue. When the dust settled, Spanish was dead and Dropper was now in charge of all the strong-arm tactics used by several unions to control their men.
Between 1920 and 1923, Dropper and his gang were responsible for more than twenty murders. But in the rackets, when you kill one competitor, another one usually comes from the shadows, intent on doing to you, what you did to the other guy, to gain control of whatever illegal activity you dominate. This person emerged in the name of Jacob “Little Augie” Orgen. Little Augie had in his stable a crew of every capable killers, which included Jack “Legs” Diamond, Louis “Lepke” Buchalter and Gurrah Shapiro. In 1922 and 1923, Dropper’s gang and Little Augie’s gang turned Manhattan into one big shooting gallery. The result was 23 murders, including the death of one innocent man, who just happened to be in the wrong place at the wrong time.
In 1923, Dropper was arrested on a concealed weapons charge. He was soon released outside the Essex Market Court, on Second Avenue and Second Street. There were rumors that a death squad may be awaiting his release, so Dropper was surrounded by a phalanx of cops as he stepped into a waiting taxi. He sat in the back seat next to Detective Jesse Joseph, when a minor thug working for Little Augie named Louis Kushner, rushed from behind the cab and shot Dropper through the closed window, twice in the head. Dropper’s wife rushed to her mortally wounded husband and said, “Nate! Nate! Tell me you were not what they say you were.”
Dropper gasped and said with his last breath, “They got me.” Then he keeled sideways, his head nestling on Detective Joseph’s shoulder.
Kushner, now restrained by several burley cops and proud of his handiwork, smiled and snapped, “I got him. Now give me a cigarette.”