Nathan Kaplan: Murder, Inc.

                      Nathan Caplin aka “Kid Dropper” – Controller of “Labor Slugging” in New York

Nathan Caplin AKA Nathan Kaplan, Jack the Dropper, Kid Dropper and 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.

Nathan Caplin was born in New York's Lower East Side on August 3, 1891. His parents, Mr. and Mrs. Joseph Caplin were Jewish immigrants from the Russian Empire. They had seven sons including Nathan.  Nathan’s mother died when he was still young. The loss of his mother was thought to have contributed to Nathan’s gradual drift into juvenile delinquency. When he was older, Nathan changed his surname to Kaplan to protect his family’s reputation and confuse police.

Nathan began committing petty thefts as a young boy and later became a skilled sneak thief and pushcart extortionist. By this time, Nathan had adopted his “Kid Dropper” persona. There are two stories regarding how he got the nickname. The generally accepted version is that at a young age, Kaplan perfected a scam known as the “drop swindle.” He surreptitiously dropped a wallet filled with counterfeit money near a stranger. Then Nathan picked up the wallet as the victim, or “mark,” was also retrieving it. As they both claimed ownership of the wallet, Nathan told the victim that he was in a rush and he agreed to hand the wallet over to the stranger in exchange for a fee and assured the victim—assuming this person did not plan to keep the money—that he could obtain a reward by returning the wallet to its rightful owner. According to The New York Times, there was a simple story behind the nickname. “He (Nathan) gained the title of ‘Kid Dropper,’” “when as a young messenger in Wall Street he knocked out those who went counter to his wishes,” usually with a blackjack. Given Kaplan’s thick, burly build and frequent thuggish demeanor, the second version seems more plausible. Either way, the legend of “The Dropper” was born among East Side gangsters.

Nathan’s first arrest was when he was just 17 for theft in February 1908 for which he was given a suspended sentence. A year later, Kaplan was then in court for concealing a weapon. The judge again gave Nathan a suspended sentence for this offence. At this point, Nathan had been preying on small merchants as well as stealing pennies from children on the streets.

Unlike many young Jewish boys who joined an East Side-based gang, Nathan came under the tutelage of Paul Kelly (Paulo Antonio Vaccarelli) who was a former boxer. Kelly headed the powerful Five Points gang. The members of the gang were primarily Italian, although there were several Jewish boys in this group.

Jay Robert Nash, a crime writer, notes, Paul Kelly was “cunning and clever … [and] an inventive criminal, the first to conceive of crime as an organized business in the U.S.” Paul Kelly also trained such notorious gangsters as Al Capone and Johnny Torrio. Kelly became wealthy through the brothels he owned as well as through his ties to Tammany Hall of the New York Democratic Party., His wealth continued to grow through extortion rackets and other corrupt practices. Over the years, Paul Kelly’s popularity declined and two of his former gang members attempted to kill him. 

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. Spanish, carried four pistols with him at all times.

Between 1920 and 1923, Dropper and his gang were responsible for more than twenty murders. There was another mobster named 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. This group were also responsible for many of the murders in New York. In 1922 and 1923, the Dropper gang and the Little Augie gang transformed Manhattan into one big shooting gallery. This shooting spree resulted in 23 murders, including the death of an innocent man, who happened to be in the wrong place at the wrong time.

One significant member of the Kelly gang was Giovanni Mistretta, or John Mestrett, as he also known; he preferred the aliases John Wheiler and “Johnny Spanish” (since he had an Italian father and Spanish mother). At some point, a bitter rivalry developed between Kid Dropper and Johnny Spanish.  

Kid Dropper decided to form his own small gang and then formed an alliance with Johnny Spanish. In 1909, Spanish started working together with "Kid Dropper."  The two soon had a disagreement over Spanish’s girlfriend, Beatrice Konstant, that culminated in a knife fight in the street; Nathan and Spanish engaged in a vicious street fight in which the Nathan nearly stabbed Spanish to death.  

When Spanish recovered, he began taking over control of a local gangster named Jacob Siegel, aka Kid Jigger's gambling operation.  However, during an especially violent gunfight due to Spanish’s attempts to gain control over the gambling enterprise, eight-year-old Rachel Rooten, an innocent bystander, was killed.

In order to evade the police, Spanish left New York for several months and hid out in Detroit and then Queens with his family.  However, upon his return, Spanish discovered that Beatrice may have been intimate with Nathan. Spanish flew into a rage and abducted the woman, who was now pregnant and as they were walking down the street. he pulled a pistol from his pocket, shot her in the abdomen, and escaped while she lay hemorrhaging on the sidewalk. The shooting was witnessed by an 11-year-old boy. Beatrice was found still alive several hours later. The baby was eventually born missing two fingers supposedly shot off by Spanish’s gun.

Spanish was apprehended by the police. He was indicted for the robbery of a saloon—however not for killing Rachel Rooten or shooting Beatrice Konstant due to a lack of evidence. Spanish confessed to the robbery and received a seven-to-10-year sentence in Sing Sing.

Meanwhile, two months later, Nathan was tried for robbing a boarding house. After he and two accomplices had taken money and valuables from the occupants of the house at gun point, Dropper had hit a woman in the head with the butt of his revolver. Similar to his rival Spanish, Nathan recieved a seven-year sentence in Sing Sing.

On Sept. 23, 1910, Spanish pursued Kid Dropper with murder on his mind.  Spanish shot Nathan in the neck as Nathan walked outside.  He fell to the sidewalk, yet survived. According to the New York Daily Tribune, “the bullet had passed out through his mouth, carrying away four of his upper teeth.” Nathan mumbled to a police officer that the shooter was “Johnny Spanish.”

Spanish was arrested for his crimes in 1911 and he was sentenced to seven years in jail which coincidentally was around the same time that Nathan was arrested for robbery. Spanish was released from prison in 1917.  He then rejoined Nathan, as well as several other former Five Point Gang members. 

However Spanish and Kaplan soon began fighting again. The Five Points gang split into two separate factions each led by one of the men who sought to gain dominance over the New York's "labor slugging" operations.  The Labor Sluggers War was a 15-year period of gang wars among New York City labor sluggers for control of labor racketeering from 1911 to 1927.

At this point, Johnny Spanish became one of the biggest drug dealers in Manhattan, selling both cocaine and heroin. His brother Joey Spanish assisted him. Yet there was too much animosity between Spanish and the Dropper for either of them to drop their guard. On July 29, 1919, Spanish was shot and killed by three assassins while entering a Manhattan restaurant. Charges were brought against Nathan, who had been identified at the scene, but were later dropped.  

By late 1917, both Nathan and Johnny Spanish were out of prison and back on the East Side. Dropper and Spanish vied for work from both garment factory owners and unions. While the two gangsters agreed “to peaceably co-exist in the underworld,” as Daniel Waugh puts it, the animosity between them endured as the competition for business intensified.

Late in the afternoon of July 29, 1919, Dropper and three of his men—Herman “Hymie” Kalman (or Kellman), William “Billy the Kid” Lustig, and Nathan Gordon—confronted Spanish as he was arriving to a rendezvous with his wife and his driver, Philip Rotkin. According to witnesses, words were exchanged and then one of the well-dressed men, either Kid Dropper or Kalman, pulled out a gun and pumped two bullets into Spanish’s chest. His wife and Rotkin ran outside as soon as they heard the gunfire and discovered Spanish lying on the sidewalk. Spanish, just 30 years old, died a short time later at Bellevue Hospital. By the evening, Kalman and Lustig were arrested for the murder. Within a few weeks, Dropper and Gordon, a member of Dropper’s gang who was believed to have been present when the shooting occurred, were all in custody. In late August, these men were indicted for first-degree murder. Yet, as it was with a great many of the charges brought against Dropper, the District Attorney’s Office had insufficient evidence to proceed to trial.

Kid Dropper had his moment in the gangster sun, at least for a few years. Prior to his imprisonment, Dropper preferred to wear slovenly attire as if he were dressing as a bum. After he became the gang boss, Dropper began wearing loud checkered suits, shirts, bold colorful ties, pointed shoes, outlandish designs, straw hats and similar attire.

Nathan was accountable for over 20 murders between 1920 & 1923. However, he was in competition with Jacob Orgen or Little Augie as he was nicknamed, who desired the control of all the illegal activities of Doppler and had chosen the best killers for his gang such as Gurrah Shapiro, Louis Buchalter and Jack Diamond. From 1922 to 1923, Manhattan was turning into a shooting arena for both the parties involved. This resulted in 23 murders including the death of an innocent man.

Spanish’s brother Joey Weiler was set on revenge. He began stalking Kid Dropper, but hold off any action until just the right moment.  That happened on the evening of Dec. 3, 1919, outside Dropper’s home—except Joey made a mistake. He saw who he thought was Kid Dropper walking beside a young woman. Joey approached the couple shooting wildly. He had actually fired at Dropper’s brother Adolph Caplin and Martha, a friend. The shots missed Adolph, but hit Martha in her abdomen. As Joey chased Adolph, a cop appeared and arrested Joey who was charged with felonious assault and illegal possession of a revolver. The woman survived the assault.

With the death of his rival Johnny Spanish, Kid Dropper had his moment in the gangster sun, at least for a few years. He earned a lot of money “slugging” for both management and unions and he got married to a young woman named Irene. In 1920, Dropper was incarcerated a few times in Blackwell’s Island penitentiary and in the spring of 1922, Dropper faced charges for conspiracy and felonious assault, however both were dismissed.

In the summer of 1923, Kid Dropper faced competition for “strong-arming” from Jacob “Little Augie” Orgen, who was released from prison after several years on a robbery conviction. Orgen immediately regrouped his gang, infiltrated labor organizations, and became Dropper’s new enemy. Violence between these two men was inevitable.

On the evening of Aug. 1, 1923, there was a shootout on the East Side between William Weiss, allied with Orgen, who was walking with his girlfriend and three or more of Dropper’s men who fired at the two from their car. Dropper himself may have been in the car. Several bystanders were hit in the shootout and a bullet missed hitting a newborn baby by inches. Weiss and Schwartz eventually recovered. A few weeks later, the police arrested Dropper and 15 of his men in the City after the Police were informed that Dropper and his gang were planning to be present at a theater strike in order to   intimidate workers.

On Aug. 28, Kid Dropper was at the Essex Market Court House, where Kid Dropper and his men were arraigned on charges related to the Aug. 1 shootout. The Judge had to release Dropper after a witness recanted and now testified that Dropper was not in the car shooting at Weiss and Schwartz. As soon as the charges against Dropper were released, the police took him into custody again for violating the Sullivan law for possession of a dangerous weapon.

Kid Dropper emerged from the courthouse with a detective at one side and with his wife, Irene at his other side. The police intended to transport Dropper uptown to another courthouse by taxi. A small crowd greeted them. Droppers wife Irene told him “Jack, you’ve beaten all other cases,” Irene told him, using his preferred first name, “and you’ll beat this one uptown.” She hugged and kissed Kid Dropper.  Dropper crawled into the taxi with the detective following.  At this point, a small, thin man pushed his way through the crowd, ran toward the taxi, took out his gun and shot three bullets through the rear window of the car.

The first shot hit Dropper in the back of his head, the second one hit the cab driver behind his ear, and the third pierced the detective’s hat. Irene reached Dropper first and pushed the shooter away, scratching his face. The man pushed Irene away and fired several more times. More police officers arrived and arrested the shooter. As an ambulance pulled up, Dropper muttered to Detective Joseph, “Jesse, they’ve got me,” before falling unconscious. Nathan Kaplan, the infamous Kid Dropper, was dead by the time the ambulance reached the hospital; he was 32.

The shooter was Louis Kerzner, alias Louis Cohen, a 19-year-old who aspired to become a full-fledged member of Little Augie’s gang. He was, as The New York Times later put it in a feature article on Sept. 9, “‘gang-struck’ as other youths are stage-struck.” Orgen did not believe Kerzner had what it took and instead used him as an errand boy. When first questioned by the police, Kerzner claimed he acted independently and that he shot Dropper because he feared Dropper would kill him.

Kerzner stated “the Dropper has been hounding me for a long time. Two weeks ago, he wanted to shake me down for $500 and when I told him I didn’t have it he said he would have me bumped off. A couple of weeks ago Louis Schwartzman, one of my best friends, was killed on the Dropper’s order. A few days ago on Essex Street, the Dropper and two of his men drew up to the curb where I was standing. They intended to get me then, but I ran away. I knew this sort of thing couldn’t continue so I went down to the court and waited for him to come out.”

The DA’s office and the police doubted Kerzner’s story and believed that Little Augie had instructed Kerzner to kill Kid Dropper, possibly by promising him that if he did so, Orgen would allow him to join the gang. It was thought that the murder was revenge for the previous attack on William Weiss and to rid Orgen of his nemesis forever. Although this theory made sense, the police found no evidence to support it and the case against Orgen and another of his men who had been charged in the murder conspiracy, was dismissed.

Kerzner was convicted of murdering Kaplan. Since there was some doubt about how this transpired, Kerzner received a 15-year prison sentence, rather than being sent to the electric chair. Kerzner was released in February 1937. Approximately two years later, Kerzner and a friend were walking down a street and both were shot dead. Kerzner was 35 years old; he had outlived Jacob “Little Augie” Orgen, who was murdered in mid-October 1927 at the age of 34, most likely on the orders of Louis “Lepke” Buchalter and Jacob “Gurrah” Shapiro over a financial dispute about the strong-arm business.

The DA’s office and the police were skeptical of Kerzner’s tale and were convinced that Little Augie had instructed Kerzner to kill Kid Dropper, possibly with the promise that if he did so, Orgen would permit him to become a gang member. The murder, it was believed, was revenge for the previous attack on William Weiss and to rid Orgen of his enemy forever. While this theory made sense, the police found no evidence to support it and the case against Orgen and another of his men who had been charged in the murder conspiracy, was dismissed.

Kerzner was convicted of murdering Kaplan. Because there was some doubt about what had transpired, Kerzner was given a 15-year prison sentence, rather than being sent to the electric chair. He was released in February 1937. About two years later, he and a friend were attacked on the street and both were shot dead. Thi was most likely on the orders of Louis “Lepke” Buchalter and Jacob “Gurrah” Shapiro over a financial dispute about the strong-arm business.

More than 2,000 people (and about 50 police detectives) attended Kid Dropper’s funeral and those closest to him, like his brothers and wife, praised him for being an “honorable son” and being a loving and loyal husband. “Why did they kill that good man?” Irene screamed.

Nathan died August 28, 1923 and is buried at Mount Hebron Cemetery in New York.

~Blog by Renee Meyers