The Life and Times of Frank Sinatra: How a Legend Became His Own Worst Enemy

Going Solo Came With Some Problems

In 1942, Frank wanted to go solo, but he was restricted by his contract with Dorsey, in which he had to give Dorsey 43% of his lifetime earnings in the entertainment industry. A legal battle went down, and they eventually settled in August 1943, but by 1942 Sinatra had stopped singing with the band. In September 1942, Dorsey said farewell to Sinatra, saying, “I hope you fall on your ass.” Their loving relationship had gone sour.

Frank Sinatra - 1942

Frank Sinatra – 1942. Photo By Rca/Kobal/Shutterstock

It was during this period that Frank’s ties to the mafia became apparent. Rumors started spreading in newspapers that Sinatra’s mob “godfather,” Willie Moretti, forced Dorsey to let Sinatra out of his contract while holding a gun to his head. Dorsey occasionally made harsh comments to the press, like “he’s the most fascinating man in the world, but don’t put your hand in the cage.” Dorsey and Sinatra never reconciled their differences by the time Dorsey died in 1956.