Introduction
Willie Nelson Opens Up: Poker Games, Life Lessons, and a Lifetime of Stories
At 91, Willie Nelson remains one of America’s most beloved storytellers—on stage and off. In a recent candid conversation, the country legend offered a rare and entertaining glimpse into his personal philosophy, late-night poker games, and some of life’s hardest-won lessons.
Nelson chuckled as he confirmed an old tale: that he sometimes played poker with friends and growers in Maui—often after sharing a bit of marijuana. “Yeah, sometimes they’d bring over a few ounces to sell and end up playing cards. And sometimes, I won their money back,” he said with a grin.
Stories like the one about Woody Harrelson—who supposedly lost $40,000 in a poker game after smoking with Willie—have become the stuff of outlaw country legend. “Not all of it’s true,” he admits, “but it sure makes a good story.”
But behind the laughter lies a thoughtful, self-aware man. Asked what makes a good poker player, Nelson replied simply, “I don’t know. I wish I knew. I win and I lose. But it helps to check a lot.”
Nelson also reflected on his friendship with Frank Sinatra, whom he called one of the greatest singers ever. “We made some records together, had a few drinks. I didn’t chase girls with him—but we had fun.”
He grew quiet as he spoke of life’s darker moments—the death of his son, his battle with the IRS, and the people who mismanaged his finances. “Losing my son—that was the lowest. Everything else pales in comparison. But if you can get through that, you can get through anything.”
Despite it all, Nelson is filled with gratitude. “The best thing that’s happened to me is my family. I’ve got great kids, and I’m proud of every one of them.”
Whether talking about playing poker in a smoky backroom or opening for Kitty Wells in Buffalo, Nelson’s stories are laced with humility, honesty, and humor. “I’m just another singer, another guitar player,” he says. But to millions, he’s so much more.
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