Frank Sinatra’s Manager and Confidant Eliot Weisman on Working With ‘Mr. S’

For three wild decades, Eliot Weisman managed one of the most iconic names in American entertainment. Frank Sinatra, whom Eliot referred to either as “Mr. S” or “The Boss,” kept Weisman on his toes throughout the Chairman of the Board’s twilight years, navigating Sinatra’s career from his 1970s comeback to his resurgence in the 1990s.

For Weisman, who also managed the likes of Liza Minnelli and Sammy Davis, Jr., the experience was a 24/7 rollercoaster ride and juggling act full of hectic days and late nights, right up until Sinatra’s death in 1997. As a result, Weisman has accumulated countless stories about his time with the boss, the basis of which makes up his book The Way It Was: My Life with Frank Sinatra(Hachette Books), out today (Oct. 24), a revealing look at the man behind the legend that chronicles everything from dates with Jackie Kennedy to fights with Donald Trump.