This is an archived article and the information in the article may be outdated. Please look at the time stamp on the story to see when it was last updated.

WGN Radio’s Dave Plier talks to Frank Sinatra’s closest confidant and an eventual member of his management team, Tony Oppedisano, about his new book called ‘Sinatra & Me: In the Wee Small Hours’. Deep into the night, for more than two thousand nights, Frank and Tony would converse—about music, family, friends, great loves, achievements and successes, failures and disappointments, the lives they’d led, the lives they wished they’d led. In these full-disclosure conversations, Sinatra spoke of his close yet complex relationship with his father, his conflicts with record companies, his carousing in Vegas, his love affairs with some of the most beautiful women of his era, his triumphs on some of the world’s biggest stages, his complicated relationships with his talented children, and, most important, his dedication to his craft.