Gus Winkler (March 28, 1901 – October 9, 1933) was an American gangster who headed a Prohibition-era criminal gang specializing in armed robbery and murder for hire with Fred "Killer" Burke.

Circumstantial evidence and testimony from Georgette Winkeler indicates that Winkler and his crew may have participated in the July 1928 murder of Brooklyn gangster Frankie Yale and the St. Valentine's Day Massacre.

Fred Burke was eventually captured and imprisoned for the first degree murder of Police Officer Charles Skelly in St. Joseph, Michigan, Bob Carey was exiled from Chicago after attempting to blackmail a friend of Capone's, and Crane Neck Nugent vanished without a trace.

Gus Winkler, along with St. Louis gangster John "Babs" Moran, was severely injured in a car accident in Berrien County, Michigan on August 3, 1931.

By the next year, Gus Winkler had carved out a lucrative position as the Outfit's boss of the former territory of Bugs Moran's North Side Gang, after Teddy Newberry requested his assistance.

Nitti and other more old school Outfit mobsters had never agreed with Capone's decision to assign positions of trust and authority to non-Italian gangsters like Gus Winkler.

In the summer of 1933, Gus Winkler was observed making visits to the Bankers Building office of FBI Special Agent in Charge Melvin Purvis.

In reality, Winkler, who had been infuriated by the unnecessary violence of the Kansas City Massacre, was helping the FBI's manhunt for fugitive perpetrator Verne Miller.

On the afternoon of October 9, 1933, while entering the beer distribution office of Charles Weber at 1414 Roscoe Street, Winkler was hit by a number of shotgun blasts fired by unknown assailants hidden in the back of a green delivery truck.