Gaspar Milazzo - Chicago's Power Struggle and Milazzo

Chicago's Power Struggle and Milazzo

As a member of Detroit's Castellammarese Clan and because he was a senior member of the clan nationwide, Milazzo found himself thrust into a growing Mafia dispute in Chicago that would spill over into every American city the Castellammarese Clan's had a presence in. By the mid-to-late 1920s the various Castellammarese Clan's that had maintained a presence within some of the biggest and well-known American cities with large Sicilian communities such as New York, Chicago, Philadelphia and Buffalo had become powerful crime families that now led or at the very least rivaled any Italian crime group within the city they operated in, this included Detroit. Milazzo had become a sort of "national councilor" within his Mafia group and because of he was frequently called upon to mediate Mafia disputes within other cities Milazzo found himself indirectly involved in a dangerous dispute within Chicago's Italian underworld that involved a fellow Castellammarese gangster and the city's leading Italian gangster who was not even a Sicilian. Giuseppe "Joe" Aiello, Chicago's Castellammarese Clan leader was struggling with Al Capone and his Capone Gang (later known as the Chicago Outfit) for control over various Prohibition era rackets such as bootlegging within South Side Chicago's Little Italy. This area of Chicago which had once been ruled by the Genna Brothers Gang, had since been taken over by Joe Aiello when 3 of the 6 Genna brothers were gunned down in 1925. Al Capone's organization coveted this territory which dominated Chicago's "home distillery" rackets because the community's Italian residents and their wine making expertise was used to operate home made liquor distilleries that were set up in apartment complexes all over the area. Another area of conflict within the Chicago Mafia was that previously Joe Aiello and Al Capone had both carried influence within the local chapter of the Unione Siciliana, but in the spring of 1929 Joe Aiello had become the Unione's leader after the murder of Giuseppe "Joseph Hop Toad" Giunta, the Unione's previous leader who Al Capone personally battered to death for betraying him. Since Al Capone was of Neapolitan descent, the Sicilian born Aiello had the upper hand and was able to thwart Capone's continuous attempts to take over the Sicilian-run organization by supporting Sicilian born gangsters to head the organization.

As a Sicilian and fellow Castellammarese, Gaspar Milazzo supported Joe Aiello in his bid to eliminate the Neapolitan Al Capone being that Joe Aiello was the recognized Sicilian Boss in the city of Chicago, but even with Aiello aligning with the forces of George "Bugs" Moran and his Irish North Side Gang, Capone still held the upper hand overall. Even with a fair size criminal organization with around 100-150 men and many associates Joe Aiello was no match for Al Capone who led a criminal organization of 300-400 made men, hundreds of associates and controlled virtually all the law enforcement and political connections within the city. New York Mafia Boss, Giuseppe "Joe the Boss" Masseria, the most powerful Mafia boss in America and a Capone ally asked Milazzo to stop supporting Aiello and proposed and alliance between themselves if Milazzo would set up Aiello for assassination. Milazzo flatly refused Masseria's offer and was greatly offended by his request, and within the Italian Mafia a perceived insult of that nature did nothing except strengthen Milazzo's resolve to support his friend Aiello who also had support from Castellammarese Clan leaders in New York, Philadelphia and Buffalo. Joe Masseria, New York's so called "Boss of Bosses" felt humiliated by Milazzo's refusal and quickly came to the realization that Milazzo was not only supporting Aiello in Chicago, but was also supporting Masseria's biggest rival in New York, Salvatore Maranzano. Maranzano was another of Milazzo's fellow Castellammarese and Masseria's greatest threat to his position of power within the New York Mafia. The Milazzo-Maranzano alliance greatly increased Masseria's determination to eliminate as many Castellammerese mafiosi as possible, including Milazzo, Maranzano, Aiello and Milazzo's old friend Stefano Magaddino in Buffalo. Masseria began plotting against Milazzo and his close associate Magaddino, the leader of a powerful Western New York crime family who Masseria believed was plotting with Milazzo to assassinated him. Masseria's first move against Gaspar Milazzo was to support Milazzo's main rival in Detroit, Cesare "Chester" LaMare, a Mafia power within the Hamtramck, Detroit area, a former Sam Catalanotte underling and a Milazzo associate.