Frank Sinatra and Donald Trump Connection Frank Sinatra reportedly told Donald Trump to "go f*** himself" in 1990 during negotiations for Sinatra to perform at the opening of Trump's Taj Mahal Casino in Atlantic City. Trump's team objected to Sinatra's fees as "a little rich" and sought to exclude opening acts like Steve and Eydie Gorme and Sammy Davis Jr., prompting Sinatra's manager to relay the blunt message after Sinatra offered to deliver it himself. Sinatra's daughter Nancy has recently reiterated that her father "loathed" Trump.
Background on the Individuals Donald Trump, born in 1946, built a real estate empire with the Trump Organization, hosted The Apprentice , served as the 45th U.S. President from 2017-2021, and was reelected in 2024 for his second nonconsecutive term starting January 2025. Frank Sinatra, the legendary singer known for standards and his Rat Pack era, was a major entertainment figure who died in 1998. Their paths crossed amid Trump's casino ventures in the late 1980s and early 1990s.
