Frank Sinatra and Winston Churchill met only once, so far as I know. On June 14, 1958, Sinatra was in Monte Carlo for the world premiere of his World War II film, Kings Go Forth. Winston Churchill was in Monte Carlo to gamble.
Despite all the missteps and bad choices that went into making it, you should buy this box. Why? Because Frank Sinatra was the greatest singer of the 20th century, and he could teach the singers of the 21st century a thing or two.