#6. His son, Frank Sinatra, Jr., was kidnapped and held for ransom
On December 8, 1963, Sinatra received a ransom demand of $240,000 for the safe return of his son. The kidnappers only allowed Sinatra to call from a payphone. During one call, Sinatra ran out of money in the middle of the call. He was horrified that the error would cost him his son’s life. After the payment was made and Frank, Jr. was safely returned, Sinatra always carried a roll of dimes, vowing to never be without coins again.