Lewis McWillie worked as a professional gambler in Memphis, Tennessee (1932-36). Later he worked in Jackson, Mississippi, and Dallas, Texas (1940-58). Then he moved to the Deauville Casino in Cuba. A fellow worker at the casino was John Martino. McWillie was also a business associate of Santos Trafficante and Meyer Lansky and later ran the Tropicana Casino in Havana. In August 1959 Jack Ruby visited McWillie.
When Fidel Castro took control of of the island McWillie was arrested and then deported to the United States. After a period in Miami Meyer Lansky placed him inside of his Tropicana Casino in Las Vegas. In 1961 Sam Giancana and Johnny Roselli recruited McWillie to look after Frank Sinatra's Cal-Neva Lodge in Nevada.
On 17th November, 1963, McWillie was seen with Jack Ruby at the Thunderbird Casino Las Vegas. According to John William Tuohy: "Two days after meeting McWillie in Las Vegas, Ruby was back in Dallas, flush with nough cash to pay off his back taxes."
In Nomenclature of an Assassination Cabal William Torbitt claims that the assassination of John F. Kennedy was organized by Louis M. Bloomfield, the head of Permindex. According to the author Permindex was comprised of:
(1) Solidarists an Eastern European exile organization.
(2) American Council of Christian Churches led by Haroldson L. Hunt.
(3) Free Cuba Committee headed by Carlos Prio.
McWillie became a professional gambler in Dallas and Las Vagas.