Before Donald Trump became the President of the United States, the New York City native was best known for being a businessman-turned-television personality, and because of his history as an entertainer, he often likes to connect himself to legendary celebrities.
Trump, 79, displayed his bizarre obsession with rock & roll legend Elvis Presley last month, boasting his so-called love for Memphis after a visit to Presley’s home. But it looks like Trump has now angered another powerful family that once orbited Hollywood.

Trump invoked the spirit of the late New Jersey-bred singer Frank Sinatra with a random post on Truth Social that eventually caught the attention of one of Sinatra’s children, who are not his biggest fans.
On April 18, the president posted a nearly four-minute video of Sinatra performing his signature song “My Way,” which was released in 1969. The clip opens with the nine-time Grammy Award winner singing, “And now, the end is near, and so I face the final curtain.”
It did not take long for Trump’s Sinatra salute to be reposted to X, where commenters on the social media platform weighed in on him using footage for some unknown reason.
One fan of the late “From Here to Eternity” film actor even tagged his daughter in a reply, “OMG, @NancySinatra will not be happy about this. Trump goes against everything that Frank stood for. He was a big champion for equality and supported the Civil Rights movement.”
Nancy, 85, agreed with the original poster’s sentiment by suggesting that Trump’s post about her deceased father was extremely disrespectful, responding to the video with a tweet that read, “This is a sacrilege.”
When another X user asked if she could do anything about Trump using the video of the showbiz icon, Nancy explained, “Unfortunately, no. The only people who can do something are the publishers.” Grok revealed that the song was not written by Sinatra; instead, it was written by Paul Anka.
Nancy also retweeted someone else stating, “This is just sickening. Frank Sinatra would never have allowed that monster in the White House to use his music or put his lyrics in his mouth. Sinatra was a man of honor, a man who never had to lie about who he truly was because he WAS the greatest. Trump is a loser.”
Another replied, “Honestly, who does Trump think he is? I’m sorry this is happening.”
A third person said, “Ughh.. Frank Sinatra would wipe the floor with Trump.” Many believe Trump will keep sharing more images as he harps over what he will never get: “He will never be as admired as Frank Sinatra. It probably eats him up inside.”
“He needs to keep your father’s name out of his filthy mouth,” demanded one commenter in defense of Sinatra. A like-minded person added, “[Your] dad deserves so much better than that piece of garbage using him like that.”
Trump rose to national prominence in the 1980s as a personification of the rich New Yorker stereotype. The tabloid headline regular became famous for his self-titled casinos in Atlantic City, New Jersey.
Sinatra was a regular headliner in Atlantic City venues, and he crossed paths with Trump in the seaside resort locale. According to Sinatra’s ex-manager, Eliot Weisman, Trump tried to lowball his client when negotiating a deal to perform at the Trump Taj Mahal Casino in 1990.
“I still remember vividly the feeling as my body flushed. I was outraged, and I lost it. I leaned across the desk and grabbed his tie, but Eric [Weisman’s son] quickly pulled me back,” Weisman wrote in his “The Way it Was” memoir, per Salon.
The passage continued, “Trump didn’t say a word or react. He didn’t call security or even throw us out of his office. We packed up our documents and promptly left. It was clear the deal was over, which I’m sure is what he wanted all along as the outcome.”
Apparently, the tension between the two entertainment juggernauts resumed with Sinatra insisting Trump could “go f–k himself,” and the casino concert negotiations obviously fell through.
Even after that confrontational interaction, Trump clearly still loves “My Way.” In 2017, he and first lady Melania Trump danced to the Paul Anka-written song at the Liberty Ball in Washington, D.C., for the presidential inauguration.
CNN reported that Nancy’s retort to Trump’s inaugural music choice was a message advising listeners to “just remember the first line of the song,” a reminder that the opening lyrics are, “And now, the end is near.”
Nancy later maintained that her “Somethin’ Stupid” duet partner continued to hold animosity towards “The Art of the Deal” author. In 2020, she backed up actress Mia Farrow’s now-deleted tweet where she claimed Sinatra would have loathed Trump by responding, “He actually did loathe him.”