Nathan Kaplan was born on the Lower East Side of Manhattan in 1891. He took to the streets as a young man and soon became involved in petty scams, such as the “eyedropper” scheme. While no one was looking, he conveniently “left” a wallet full of counterfeit money on the sidewalk. Then he would immediately “find” the wallet and look for a fool, to whom he said: “Look, 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 money from the reward will be “. And the dupes were constantly doing this for Kaplan, hence the nickname “Kid Dropper.”
Due to his moneymaking background, Dropper joined Paul Kelly’s (Paolo Vacarelli) Five Points Gang, which was quite unusual for the Jewish Dropper, as the vast majority of Kelly’s gang members were of Italian descent. However, Dropper didn’t last 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 disbanded, and Dropper, considered a petty criminal before going to jail, envisioned himself as Kelly’s successor and took over Kelly’s work racket business.
In his past life, Dropper was a regular user of scruffy good looks, that is, he dressed like a tramp. Now as boss, Dropper stared to dress accordingly. He threw down his usual rags and started walking the streets in gaudy plaid suits, pointy shoes, shirts and ties in bright colors and flamboyant designs, with a straw hat, or a derby, leaning casually over one eye. Dropper compiled a smorgasbord of low-level gangsters and called their gang, “Jack Dropper’s Rough Riders.” But Dropper soon found himself in a war for control of Kelly’s old businesses with an old enemy, who had also just been released from prison.
Before his incarceration, Dropper had become a very bad enemy in his partner Five Pointer Johnny Spanish, a Spanish Jew, real name Joseph Weyler. The two men had been friends, until 1911, when Spanish had to take the lead in a shooting that resulted in the death of an innocent eight-year-old girl. Spain divided the city for a few months and when he returned, he discovered that Dropper had stolen his girlfriend. Spanish, who carried four guns with him at all times, proceeded to pepper his former love with multiple shots. Somehow the woman survived, but the Spaniard received seven years in prison for his actions. When he was released in 1917, Spanish targeted Dropper and all the illegal activities that Dropper controlled. Each man had roughly three dozen shooters under their wings, and these shooters went to work, resulting in the death of several men on both sides. But the war ended, when Dropper got Spanish, so to speak, after he and two of his men ambushed the Spanish as he was leaving a restaurant at 19 Second Avenue. When the dust settled, Spanish was dead and Dropper was now in charge of all the heavy-handed tactics used by various unions to control their men.
Between 1920 and 1923, Dropper and his gang were responsible for more than twenty murders. But in rackets, when you kill a competitor, another usually comes from the shadows, with the intention of doing to you, what you did to the other, to gain control of any illegal activity that you master. This person came up on behalf of Jacob “Little Augie” Orgen. Little Augie had a team of all capable assassins in his stable, 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 a great shooting gallery. The result was 23 murders, including the death of an innocent man, who was in the wrong place at the wrong time.
In 1923, Dropper was arrested on a concealed weapons charge. He was soon released in front of the Essex Market Court, on Second Avenue and Second Street. There were rumors that a death squad might be awaiting his release, so Dropper was surrounded by a phalanx of police officers when he got into a waiting taxi. He sat in the backseat next to Detective Jesse Joseph, when a lesser thug working for Little Augie named Louis Kushner ran out from behind the cab and shot Dropper through the closed window, twice in the head. Dropper’s wife ran up to her mortally wounded husband and said, “Nate! Nate! Tell me you weren’t what they say you were.”
Dropper gasped and said with his last breath, “They caught me.” Then he slumped on his side, his head resting on Detective Joseph’s shoulder.
Kushner, now held back by several Burley cops and proud of his work, smiled and snapped, “Got it. Now give me a cigarette.”