[1] Already involved in organized crime in Calabria,[1] Luppino, his wife Domenica (née Todaro)[2] and their 10 children immigrated to Hamilton, Ontario in 1956, from Castellace, a subdivision of Oppido Mamertina.
[5] By the time Luppino arrived in Canada, the "Three Dons" had already been established, consisting of Santo Scibetta, Anthony Sylvestro and Calogero Bordonaro, who answered to Stefano Magaddino of the Buffalo crime family.
[7] By the early 1960s, Magaddino promoted Santo Scibetta to leader of the Buffalo family's Ontario branch replacing Johnny Papalia who was under indictments in the United States.
[15][16] Luppino and Santo Scibetta also answered to Magaddino while Papalia was imprisoned in Canadian and American prisons between 1962 and 1968.
[20] The wedding brought together the elite of the Canadian Mafia being attended by Vincenzo Cotroni and Lugi Greco of Montreal, Johnny Papalia of Hamilton, Paul Volpe of Toronto, and Joe Gentile of Vancouver.
[21] Luppino saw himself as upholding traditional Italian values against what he saw as the corrupting consumerism of North American society.
[22] In a phone conversation with Magaddino, Luppino told him in Italian: "I, Don Stefano, do things for my own dignity".
[22] Luppino lived in a modest house on Ottawa Street South on the east end of Hamilton.
[23] His only known source of income was his veterans' pension from his service in the Regio Esercito in World War I, a sum of lire that amounted to the equivalent of CAD$175 per month.
[23] Luppino greatly disapproved of the social changes of the 1960s and endlessly bemoaned that the younger generation of Italian-Canadians were materialistic, self-interested, and lacked respect for older men such as himself.
[5] In 1967, police began a five-year surveillance operation of Giacomo Luppino, which included wiretapping his Hamilton home.
[25] In 1966, when Magaddino planned to have Cotroni killed for his loyalty to Joe Bonanno, Luppino persuaded him to abandon the murder plot.
"[5] In another wiretapped phone call, Luppino told Violi that he wished his English was better so that he could set up his own business because "people here are much easier to cheat than in Italy".
There was the big boss of the mob, out raking the leaves in his yard, wearing an old grey sweater and a felt hat.
Luppino together with Michele "Mike" Racco of Toronto and Frank Sylvestro of Guelph, were the only non-Montreal Mafiosi to make the trip to Montreal to attend Violi's funeral.
[33] Following the example set by the Musitano family, Luppino started to employ outlaw biker gangs as subcontractors.
[34] A report in the Hamilton Spectator in October 1980 stated that: "A group headed by Giaccomo Luppino of Ottawa Street South, the closest thing Canada has to a Hollywood-style 'Godfather' has established a pipeline with the bikers for contract work...The bikers are being played for suckers in the incidents, taking all of the heat and very little of the profit.