Although Frankie Yale was a New York mobster he was close with Johnny Torrio and Al Capone, both of Chicago. Yale was John Torrio's partner in the Five Points Gang in Brooklyn and had killed a dozen men before his twenty- first birthday. When Torrio left for Chicago, Yale took over all the gang's rackets in NY. Whilst Al Capone was working for Frank Yale, he began to draw the attention of NY's finest and Yale got in touch with Torrio so Capone could go to Chicago to work with the outfit there.

The association of these three did not end here. Yale's killing expertise was called upon a number of occasions. Yale was useful to the Chicago mob because he was unknown in the city and could easily appear and disappear in order to murder the Outfit's marked men.

On May 11, 1920, Yale was in Chicago to knock off Big Jim Colosimo for Torrio and Capone. Yale hid in the coat check room of Colosimo's cafe, jumped him, and fired two rounds into his body. Colosimo died minutes later. Yale was also used in the Dion O'Banion hit ordered by John Torrio. Yale and two others shot O'Banion in his flower shop.

In 1928, Capone, who now led the Chicago mob, and Yale began to lose faith in each other. Capone had been using Yale as a conduit for illegal booze shipments from Long Island and these shipments began to run into trouble. More and more of the trucks and boats loaded with booze were being hijacked. Capone sensed a double cross and sent one of his men to spy on Yale. The spy, Jim De Amato, was discovered and shot dead on a Brooklyn street. But before his death, De Amato had already confirmed Capone's suspicions. Yale was hijacking Capone's shipments and then selling booze back to him. On top of this, Yale was trying to acquire interests in Chicago agaisnt Capone's wishes. Capone gave the order to have Yale whacked.

On July 1, 1928, Yale was driving along 44th Street in Brooklyn when a black sedan forced him to the curb. The occupants of the sedan riddled Yale's car with bullets from .45 caliber pistols and Thompson sub-machine guns. Some of the weapons were recovered at the crime scene and the Thompson sub-machine gun was traced to a dealer in Chicago. This was the first time the Tommy gun was used for a hit in New York.