It is speculated that Harry, through links with gangster Frank Costello, moved alcohol, now illegal during the prohibition, along with legitimate Canadian pulp paper across the border.
In earlier years, Hot Springs had fallen under the influence of such mobsters as Al Capone, Frank Costello, and Charles "Lucky" Luciano, who was arrested in New York City along with the Hot Springs chief of detectives on charges of ninety counts of prostitution brought by District Attorney and later Governor Thomas E. Dewey.
Maestri and the Longites had reached a deal with mobster Frank Costello whereby the city would ignore slot-machine laws in exchange for a cut of the proceeds, so prostitution and illegal gambling flourished in New Orleans under Maestri’s tenure.
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Flemmi is the basis of Frank Costello's chief enforcer and contract killer "Arnold French" portrayed by Ray Winstone in the 2006 crime thriller The Departed.