The St. Louis Family
The Cuckoos were headed by the three Tipton bothers, Herman, Ray and Roy. The gang earned a reputation for being "fast and willing shooters who would fight anyone, including themselves. Extortion from bootleggers and other gangs, robbery, kidnapping and murder for fun and profit were Cuckoo specialties."
It was Roy Tipton who planned the 1923 mail truck robbery that netted its participants $2.4 million and 25 years in prison. The Cuckoos suffered minor losses in manpower from the convictions and continued on. A few months later the losses began to mount. Gang members Oliver Hamilton and Clarence "Dizzy" Daniels were sentenced to life in prison, and August "Gus" Webbe was sentenced to 10 years for the killing of St. Louis Officers Edward Griffin and John Surgant during a robbery. This was followed by Joseph "Mulehead" Simon, Jimmy Michaels, and Ben "Melonhead" Bommarito being arrested for the armed robbery of a jeweler and the attempted robbery of a shoe company payroll. Next came Milford Jones, implicated in a robbery with Carl, Bernie, and Earl Shelton. Bennie Bethel was a suspect in a Pine Lawn bank robbery, while Joseph Costello, Marvin Paul Michaels and Alfred Salvaggi were questioned in the deaths of the aforementioned John and Catherine Gray.
In 1925, Cuckoo Gang member Tommy Hayes was released from prison after serving time for a mail / payroll robbery in January 1921 in Wood River, Illinois. Hayes was considered an unusual gangster because he came from a respectable family, didn't drink or smoke, and worked out to stay in shape. Hayes' police record began in 1913 when he was 15. By the early 1920s, he had become "an efficient killer."
In the mid-1920s the Cuckoos survived a gang war with the Green Ones, in which 13 mobsters were killed. It was rumored that a truce was declared after a three-day peace conference was held between Herman Tipton and Green Ones' leader Giannola. The agreement ended when Tony "Shorty" Russo, and his brothers led a splinter group away from the Green Ones. The leadership of this renegade group was short lived when Russo and Vincent Spicuzza were found slain outside Chicago, each with a nickel in their hands, the trademark murder signature of Al Capone gunman "Machine Gun Jack" McGurn. Authorities believed the two were trying to collect a $50,000 bounty put on Capone by rival Joe Aiello.
The war continued for another two years, during which another dozen plus mobsters were killed. Among them were James Russo and Mike "the Chink" Longo, both murdered by Tommy Hayes. The war came to an end on July 29, 1928 after St. Louis police escorted the surviving Russo brothers William, Thomas, and Lawrence to the Union Station so they could get out of town alive.
The Cuckoos were soon involved in another gang battle as they lent their guns to Carl Shelton's East Side Gang to fight the Birger Gang. When the Birger Gang was eliminated in 1930, Shelton ordered the Cuckoos out of the East Side. When Herman Tipton refused to leave because of the sudden bootlegging wealth he was enjoying there, Shelton convinced Hayes to split from the gang and turned on Tipton. Another dozen or so killings took place during this faction war. In February 1931, Hayes led an attack on a roadhouse in which three Shelton men were killed. Shelton, suspecting a double-cross, in turn double-crossed Hayes on April 15, 1932. Hayes was found in Madison, Illinois with 12 slugs in his back. His death effectively ended the Cuckoo gang as a force in the St. Louis underworld, although, as with Egan's Rats members, many ex-Cuckoos would be around for decades.