It's no secret that MAGA Republican President Donald Trump hasn't been able to attract the cream of the crop when it comes to the entertainment industry. While Kid Rock, Kevin Sorbo and Scott Baio are Trump ride or dies, pretty much every other Hollywood or music legend or rising star is taking a pass on Trump.
And some outright despise the man and let everyone know. Often.
So is it any wonder that the MAGAsphere is now sifting through cemeteries to find someone of note to support their leader?
A Trump troll—with an AI generated photo of Frank Sinatra in a MAGA hat—recently decided to comment on a post by Nancy Sinatra. She had shared a Forbes article about her father's music making it onto two Billboard charts in 2025.
Completely unrelated to her actual post, the MAGA minion claimed her father would support Trump.
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Not giving him the attention he so desperately craved from her, Nancy didn't reply to his comment directly.
Instead she reposted it with the statement:
"Not a chance. You obviously don't know my father at all. Do some homework before you post about him."
@NancySinatra/X
Nancy Sinatra has been a vocal critic of Trump for years.
In 2021, responding to a question about Trump's 2016 electoral college win, she told The Guardian:
"I couldn’t believe that this great nation had sunk so low.. I’ll never forgive the people that voted for him, ever. I have an angry place inside of me now. I hope it doesn’t kill me."
She also shares her distaste for The Donald—as he called himself since the 1980s—frequently on social media:
As does Frank Sinatra's ex-wife Mia Farrow.
People agreed that the Chairman of the Board—a longstanding nickname for Sinatra along with Ol' Blue Eyes—wouldn't be a fan of Trump.
And they let the Trump troll and Nancy Sinatra know.
Fans of Frank Sinatra actually debated the issue in the subReddit dedicated to the singer.
They overwhelmingly decided Frank would be no friend of Donald Trump.
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In his book The Way It Was, Eliot Weisman—Sinatra's manager for 23 years from 1975 until the singer's death in 1998—shared the time the singer was going to perform at the opening of Trump's Taj Mahal in Atlantic City in 1990.
The performance never happened because of Trump's negotiating prowess and keen business sense.
In final negotiations on a deal already set up by Trump associate Mark Grossinger Etess, Trump told Weisman that Sinatra was "a little rich" for the already agreed upon price and that he'd decided to drop Sammy Davis Jr.—who was dying of cancer at the time—and duo Steve and Eydie, who were the other acts in the original deal.
Trump then asked Weisman who popular duo Steve Lawrence and Eydie Gormé were. Weisman claimed he tried to strangle Trump with his own tie, but Weisman's son was at the meeting with him and stopped his father from throttling The Donald.
When Weisman stepped out of the meeting and called Sinatra to tell him what happened, the iconic crooner gave Weisman two choices: tell Trump he should go f*ck himself on Sinatra's behalf, or give Trump's phone number to Sinatra so he could personally call Trump to tell him to go f*ck himself.
Weisman wrote that he returned to Trump's office and gladly told Trump:
"Sinatra says go f*ck yourself!"
It's impossible to know exactly what Frank Sinatra would say about today's political climate in America, but his life and his family and close friends can give insight.
And they're a resounding "no!" on the Chairman of the Board ever being a MAGA minion.
@realDonaldTrump/Truth Social
@realDonaldTrump/Truth Social
Ronald Grump the Muppet in 1988; Joe Pesci as Ronald Grump in 1994; Donald Grump in 2005PBS
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PBS
