David “Chippy” Robinson was born in 1897 in the tough, working-class neighborhood of Baden in North St. Louis, Missouri. Originally named David Michael Robison, he grew up in a city torn between corruption, political violence, and the booming underworld economy of bootlegging and vice. By his teenage years, he had joined the infamous Egan’s Rats, a powerful St. Louis gang known for their dominance during the Prohibition era.

Chippy’s early brushes with the law began by the mid-1910s, and he was already making a name for himself when he and fellow gang member Tony Ortell were caught burglarizing a North Side gas station in 1918. The robbery went sideways when they were surprised by a man named Charles Hoffman, who shot and wounded Robinson before being fatally shot himself.

Despite his youth, Chippy was quickly rising in the ranks of the Egan’s Rats. His close friendship with William “Dint” Colbeck, the right-hand man of boss Willie Egan, solidified his position. Known for his cool demeanor and deadly accuracy with a gun, Chippy became the gang’s top marksman—often spending hours in target practice when not actively committing robberies or organizing hits. He had blonde hair, piercing blue eyes, and a medium build—but his calm exterior masked a volatile temper, worsened by alcohol.

Robinson developed a twisted sense of humor and cruelty. When drinking, he was known to fire bullets at the feet of fellow gang members just to watch them “dance” in fear. Friends often fled his presence when he drank, fearing what mood he might swing into. As Prohibition swept the nation, Chippy transitioned from burglaries to armed robberies, political intimidation, and contract killings. His name became feared across St. Louis.

The peak of Chippy Robinson’s violent career coincided with the Prohibition-era gang wars in St. Louis. After the assassination of boss Willie Egan, the Egan’s Rats declared open war on the Hogan Gang, a bloody feud that consumed the city’s underworld. Robinson was a prime suspect in many of the retaliatory strikes, killings, and bombings that occurred during this period. He was also heavily involved in lucrative heists, including repeated raids on a Jack Daniel’s warehouse, stealing and reselling large quantities of whiskey.

But Robinson’s most disturbing acts weren’t always about business—they were personal, unpredictable, and laced with sadism. On May 26, 1923, Robinson and fellow gang member James “Sticky” Hennessey lured minor associate Joe Powderly to a resort in Staunton, Illinois. After a night of drinking, Chippy coldly informed Powderly he intended to kill him. As Powderly tried to run, Chippy gunned him down. On the return trip to St. Louis, Chippy propped up Powderly’s corpse in the car, shoved a cigar in his mouth, and made jokes as if the dead man were still alive.

Later that same year, another chilling episode occurred. While drinking with safecracker Billy Grant, his wife Rosie, and another man, Chippy became enraged over a comment made by Grant. He robbed the group and, without hesitation, pulled out two pistols and gunned down all three in front of a crowd at a nightclub—reportedly laughing as he did it.

Eventually, Robinson’s luck ran dry. On November 15, 1924, he and eight of his fellow Egan’s Rats were convicted of a high-profile mail robbery and sentenced to 25 years in prison. He was transferred to Atlanta Federal Penitentiary, but prison didn’t stop his reach. In 1926, he arranged the murder of Jack Barrett, who was reportedly pursuing Chippy’s wife, Mabel. Barrett was found shot to death on November 22 of that year—a crime widely believed to be orchestrated from behind bars.

Robinson was released on parole in February 1941, returning to a changed underworld. Though older, he was still a feared name. He and the remnants of the Egan’s Rats attempted to regain control in St. Louis, but the criminal landscape had shifted. When his old friend and gang leader Dint Colbeck was machine-gunned to death on February 17, 1943, Robinson was interrogated but never charged. He was later linked to the 1944 abduction and murder of gangster Patrick Hogan, and in 1946, faced extortion charges alongside Steve Ryan—both men were acquitted.

In his later years, Chippy was believed to be working under East St. Louis crime boss Frank “Buster” Wortman, though much of his activity faded into obscurity. Unlike many of his peers, David “Chippy” Robinson died peacefully in 1967.