As a young man in Brooklyn, Yale befriended Johnny Torrio and Capone. At the time Capone was taking over the rackets in Chicago, Yale was assuming control of Joe Masseria's operations in Brooklyn.

There is some disagreement over Yale's perceived role in the Unione Siciliana. Some historians have written that Yale rose to the national presidency of that organization (and that would explain some of the details of his later life). Other historians argue that Yale could not have occupied any position of importance in the Unione because he was not Sicilian. (A few historians stubbornly insist that the Unione itself did not exist outside the confines of Chicago. That claim is contradicted by a national convention known to have been held at Cleveland.)

Yale immigration records from the early 1900s state that he was born in Calabria on the mainland of Italy. But those rely on statements from Yale himself. So, the matter of his place of birth is still in question.

What is known for certain is that Yale affiliated himself with the local Brooklyn toughs from an early age. His police record stretches back to a 1912 charge for disorderly conduct. He was arrested numerous times for more and more serious charges, but his only convictions were for disorderly conduct and a violation of the Sullivan Act (carrying a weapon).

In November of 1924, Dion O'Banion was gunned down in his Chicago flower shop days after local Unione President Mike Merlo died of cancer and six months after O'Banion tricked Johnny Torrio into buying the Sieben Brewery. (The brewery was immediately raided by police, and Torrio was arrested.)

Some days after the O'Banion murder, Yale and his companion Sam Pallacio, also of New York, were arrested by Chicago police as they boarded the Twentieth Century Limited train for Gotham. The two men were questioned about O'Banion, but they were able to prove alibis and were let go. If Yale was an official of the Unione Siciliana, he could have been in Chicago for Merlo's funeral rather than O'Banion's murder.

During Prohibition, Yale illegally imported vast quantities of alcohol and shipped some west to Capone. Capone, who was continually frustrated by others' control of his booze supply, sought an increased flow of alcohol from Brooklyn and also worked to seize the Chicago Unione Siciliana and its affiliated home-based wine producers.

Yale and Capone had a sudden falling out. The press of the time believed it had to do with Capone's meddling in the Chicago Unione. After Merlo, Unione presidents were murdered in rapid succession as Capone attempted to install a friendly regime and open the group to non-Sicilians. A Unione-affiliated Yale would have had reason to oppose Capone's shenanigans. Yale reportedly ordered Capone ally Tony Lombardo to surrender the Unione presidency in January 1928.

Yale at that time engaged in the odd practice of hijacking his own westward liquor shipments. Some say he was trying to compensate for Capone's non-payment of other shipments while still preserving his relationship with the Chicago gangster. If so, it didn't work.

Yale was attacked several times in 1928. He was finally shot to death in his car in a residential Brooklyn neighborhood on July 1, 1928. Some of Capone's men were noted in New York at the time. Police later found connections between the Yale killing and the St. Valentine's Day Massacre.

Eastern gang leaders seemed to discipline Capone for killing Yale (his projection of power into New York and his continuing offenses against the Sicilian underworld could not be overlooked) and for prompting waves of negative publicity with the Chicago massacre. Capone was called to a regional meeting in Atlantic City. Following that, he allowed himself to be arrested, convicted and imprisoned in Pennsylvania.