An intimate, revealing portrait of Frank Sinatra—from the man closest to the famous singer during the last decade of his life.

More than a hundred books have been written about legendary crooner and actor Frank Sinatra. Every detail of his life seems to captivate: his career, his romantic relationships, his personality, his businesses, his style. But a hard-to-pin-down quality has always clung to him—a certain elusiveness that emerges again and again in retrospective depictions. Until now.

From Sinatra’s closest confidant and an eventual member of his management team, Tony Oppedisano, comes an extraordinarily intimate look at the singing idol. 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.

Toward the end, no one was closer to the singer than Oppedisano, who kept his own rooms at the Sinatra residences for many years, often brokered difficult conversations between family members, and held the superstar entertainer’s hand when he drew his last breath.

Featuring never-before-seen photos and offering startlingly fresh anecdotes and new revelations that center on some of the most famous people of the past fifty years—including Jackie Kennedy, Marilyn Monroe, Sam Giancana, Madonna, and Bono—Sinatra and Me pulls back the curtain to reveal a man whom history has, in many ways, gotten wrong.

Tony Oppedisano—a.k.a. “Tony O”—is a former professional musician and singer who went on to become an award-winning producer and personal manager to entertainment icons Frank Sinatra and Don Rickles. Tony met and befriended the singing legend when the younger man was only twenty-one years old. He later became Sinatra’s best friend and road manager, a contributor to two of the singer’s platinum albums, and a producer of the documentary To Be Frank: Sinatra at 100. Tony grew up in Brooklyn, New York, and currently lives in Los Angeles. He is the author of Sinatra and Me.

Mary Jane Ross has collaborated on numerous bestselling memoirs, including books by Albert DeMeo, Ray Charles Robinson Jr., Nancy Mace, and Piper Laurie.