In a new interview, Willie Nelson said he once played Trump’s Atlantic City resort and knows the president “pretty good.” Credit: Shutterstock / Randy Miramontez

Given his politics, it might surprise some fans to learn that Willie Nelson once worked for Donald Trump.

But that’s just one of the revelations gleaned from a Sunday interview with the Guardian about the legendary Texas singer-songwriter’s forthcoming book The Last Leaf: Reflections on Late-Life Creativity — and My Longest Love Affair.

The memoir, to be released Tuesday through Telegraph Books, details a wild ride of drugs, sobriety and a brush with death from COVID-19. But the centerpiece is Nelson’s 40-year marriage to his wife, Annie D’Angelo, whom he calls his “pet rattler,” “best friend” and the “heroine” of the story.

During the interview, Nelson said he actually knows President Donald Trump “pretty good” and they go “way back.” While he said the pair disagree on politics, the musician said Trump “likes music” and paid him well when he played one of the mogul’s casinos.

The gig occurred long before Trump ventured into politics, according to the Guardian. Though Nelson didn’t specify when or at which casino he performed, Trump’s involvement in the Atlantic City casino industry spanned the ’80s and ’90s and included properties such as Harrah’s at Trump Plaza, Trump Castle and Trump Taj Mahal.

“I worked for him for two weeks at his resort in Atlantic City. The money was good,” Nelson told the publication. “He came out and thanked me for doing it. I shook his hand. We disagree on politics probably 100%, but he likes music.”

Despite their brief time working together, Nelson said he’s not a fan of Trump’s actions in office.

“I disagree with a lot of the things he’s tried to do,” Nelson told the Guardian. “Practically everything he’s tried to do.”

A longtime, outspoken Democrat, Nelson has supported Beto O’Rourke and other Democratic candidates, particularly in his home state. Nelson, whose primary residence is still in the Hill Country town of Spicewood, recently endorsed Texas U.S. Sen.-elect James Talarico and Gov.-elect Gina Hinojosa during the midterms.

Indeed, Nelson has publicly criticized President Trump’s zero-tolerance immigration policy, calling the separation of migrant children from their parents “outrageous.”

“Christians everywhere should be up in arms. What happened to ‘Bring us your tired and weak and we will make them strong?’ This is still the promised land,” Nelson said in a June 2018 statement.

Nelson also issued a challenge to President Trump, tweeting at him directly and inviting him to tour a detention center with him to “better understand what’s happening down there.”

At 93 years old, Nelson takes the long view on politics these days.

“Well, you know, I’ve watched a lot of presidents come and go,” Nelson told the Guardian. “We vote ’em in. And when we don’t like it, we vote ’em out.”

Speaking of the latter, Willie debuted a song called “Vote ’Em Out” at a Democratic rally in Texas ahead of the 2018 midterms.

Although Texas came close to voting U.S. Sen. Ted Cruz out of office in 2018, with O’Rourke narrowly losing that race, the song experienced a resurgence in the run-up to the most recent election. This time, Texans did vote out a statewide slate of Republicans.


Texas politics is a mess. We make it a readable mess.



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Stephanie Koithan is the Digital Content Editor of the San Antonio Current. In her role, she writes about politics, music, art, culture and food. Send her a tip at skoithan@sacurrent.com.