After Prohibition, they smuggled liquor from Windsor, Ontario, across the Detroit River in Canada, and used many other waterways between the two countries, selling the illegal products at great profit.

[citation needed] Zerilli began working with mobster Gaspar Milazzo to expand into loansharking, extortion, narcotics, labor racketeering, and bookmaking.

In 1930, following the murder of Milazzo by New York mobsters, the Purple Gang became involved in syndicate gambling operations.

In 1931, Lucky Luciano of New York formed The Commission, which initially consisted of seven family bosses: the leaders of New York's Five Families: Charlie "Lucky" Luciano, Vincent Mangano, Tommy Gagliano, Joseph Bonanno, and Joe Profaci; Chicago Outfit boss Al Capone; and Stefano Magaddino, boss of the Buffalo, New York family.

In 1950 the younger Zerilli, then in his early 20s, had become a majority owner of the Hazel Park Raceway (with family help); it was located in suburban Detroit.

With gambling in Michigan limited to betting at racetracks, Hazel Park generated millions of dollars in revenue for the Detroit Partnership.

But after he was convicted and imprisoned for conspiring to conceal interests in a Las Vegas syndicate casino, in 1975 Zerilli came out of retirement to lead as boss.