Dean Martin's Connections with the Mafia
Like many other singers at the time, Dean Martin is rumored to have had some connections with the mafia, both at a personal and a professional level. A biographical book of Dean Martin by Michael Freedland published in 2005 claims to reveal these connections. The book also talks about Dean Martin's insecurities despite the fact that he was always perceived as a cool and laid-back man.
Connections to the mafia were rooted in the singer's early career, when he was trying to make his way in the entertainment business. At that time, mob bosses who were running saloons in Chicago used to help him out by getting him more concerts. Later on, when he became famous, Martin returned their favors by singing at certain events where they called him. It is said that if Sam Giancana, a famous mobster in Chicago back then, told someone to bring Dean Martin over because he needed him for ten days, there would have been no inconvenience at all despite the fact that he could have got into troubles. The author does not suggest that Dean Martin did anything else for the mafia other than these small favors. He implied that the singer felt some sort of sympathy for the mob for helping him out in his early years. However, the FBI once discovered a plan of the mafia to kill Dean Martin specifically for his lack of gratitude for their favors.
Another book by John Smith states that Dean Martin was good friend with Antonio Fiato and Johnny Roselly, two famous mobsters at that time. John Smith writes that Antonio Fiato has done Martin many favors. For example, he once got his money back from two swindlers who had cheated his ex-wife Betty Martin taking thousands of dollars from her alimony.
Dean Martin was not the only singer said to have had connections with the mafia. Frank Sinatra, for instance, had relations with many mafia mobsters including Sam Giancana, Carlo Bambino, Joseph Fischetti and Lucky Luciano. The FBI kept Sinatra under surveillance for almost fifty years starting in the early '40s.
Dean Martin denied any connections with the mafia until the day he died.