Nathan Kaplan was born on the Lower East Side of Manhattan in 1891. He hit the streets as a young man and soon became involved in petty scams, such as the “dropper” scheme. While no one was looking, he would conveniently “drop” a wallet full of counterfeit money on the sidewalk. He would then immediately “find” the wallet and search for a fool, to whom he would say, “Look, I don’t have time to track down the owner. Take the wallet and find the owner. Give me half of what you think.” the reward money will be.” And the dupes constantly did this for Kaplan, hence the nickname “Kid Dropper.”

Due to his background in making money, Dropper joined Paul Kelly’s (Paolo Vacarelli) Five Points Gang, which was rather unusual for the Jewish Dropper, as the vast majority of Kelly’s gang members were of Italian descent. However, Dropper did not 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 launched in 1917, Kelly’s gang had disbanded and Dropper, considered a petty criminal before going to jail, believed himself to be Kelly’s successor and took over Kelly’s labor racket business.

In his past life, Dropper was a regular wearer of scruffy clothes, in other words, he dressed like a homeless man. Now as boss, Dropper looked to dress accordingly. He threw off his usual rags and began prancing through the streets in gaudy checked suits, pointy shoes, shirts and ties in bright colors and outlandish designs, with a straw hat, or bowler, cocked jauntily over one eye. Dropper compiled a ragtag crew of low-level gangsters and named his gang, “The Rough Riders of Jack Dropper.” But Dropper soon found himself embroiled in a war for control of Kelly’s old businesses with an old enemy, who had also just been released from prison.

Prior to his imprisonment, Dropper had made a very bad enemy in fellow Five Pointer Johnny Spanish, a Spanish Jew, whose real name was Joseph Weyler. The two men had been friends, until 1911, when Spanish was on the run from a shootout that resulted in the death of an innocent eight-year-old girl. Spanish was cut off from town for a few months and when he returned, he found that Dropper had stolen his girlfriend. Spanish, who carried four pistols with him at all times, proceeded to pepper his former flame with multiple shots. Somehow the woman survived, but the Spaniard got seven years in prison for his actions. When he was released in 1917, the Spanish targeted Dropper and all illegal activities controlled by Dropper. Each man had approximately three dozen marksmen under his wings, and these marksmen went to work, resulting in the deaths 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 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 syndicates to control his men.

Between 1920 and 1923, Dropper and his gang were responsible for more than twenty murders. But in scams, when you kill one competitor, another often comes out of the shadows, intent on doing what you did to the other, to gain control of whatever illegal activity you dominate. This person came up with the name Jacob “Little Augie” Orgen. Little Augie had in his stable a crew of all capable assassins, including Jack “Legs” Diamond, Louis “Lepke” Buchalter, and Gurrah Shapiro. In 1922 and 1923, the Dropper gang and the Little Augie gang turned Manhattan into one big shooting gallery. The result was 23 murders, including the death of an 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 in front of the Essex Market Court, at Second Avenue and Second Street. There were rumors that a death squad might be waiting for his release, so Dropper was surrounded by a phalanx of policemen when he got into a waiting taxi. He was sitting in the back seat next to Detective Jesse Joseph, when a minor thug working for Little Augie named Louis Kushner ran out from behind the cab and shot Dropper twice in the head through the closed window. Dropper’s wife ran to her mortally wounded husband and said, “Nate! Nate! Tell me you weren’t what they said you were.”

Dropper gasped and said with his dying breath, “They got me.” He then leaned to the side, his head resting on Detective Joseph’s shoulder.

Kushner, now held back by several burly cops and proud of his work, smiled and snapped, “Got it. Now give me a cigarette.”