2. Jerry Weintraub
Former chairman and CEO of United Artists
Fired a fictional character so Sinatra wouldn’t boot him
Without any real experience, Jerry Weintraub was able to persuade Frank Sinatra and Elvis Presley to make him their manager. He went on to become one of the most respected, feared, and loved names in the entertainment industry. Jerry was taught the lessons of “fake it till you make it” from his father, who as a gem dealer, claimed he owned the world’s largest and most expensive gem. No one found out the thing was a fake until his death years later.
While managing Frank Sinatra on tour, Jerry was almost fired by the great legend. Sinatra was not happy about the hotels and service or the gigs he was getting so he gave Jerry his marching orders. Jerry convinced him to hold off from firing him for just six hours. He came back to Sinatra and said, “listen, everything’s ok now. I fired Ferguson and all the problems are fixed, and everything you complained about will now be exactly as you wanted”.
Sinatra of course asked who Ferguson was. Jerry told him that he was the man in charge of organising everything on tour. Sinatra was satisfied and Jerry continued to manage him for years to come. Turned out Ferguson, who took the blame, never actually existed.