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When I came to FIREas a young free speech advocate in 2012, part of my training was learning about the “old guard”: the tireless advocates who came before me and that shape our current understanding of free expression.

This weekend, we lost a giant of that old guard. Nat Hentoff died of natural causes last night at his Greenwich Village apartment at the age of 91. , Nick Hentoff, he died surrounded by family while listening to Billie Holiday.

For well over 60 years, Nat was a familiar byline to free speech trumpeters, civil rights activists, jazz aficionados, New Yorkers, and citizens the world over who took joy in “being out of step.”

He wrote for , , , , and many more publications. He was also a pioneering crafter of “” for his beloved friends who played jazz music. In 2004, Nat was the first non-musician to receive the title of by the National Endowment of the Arts.

While I could never claim to be his friend, I came to know Nat in my role as the assistant to FIREPresident Greg Lukianoff. He was on ��֭����’s board of advisors and wrote regularly and eloquently on our issues. Occasionally, he would call Greg and ask us to send him some information about a case. Nat didn’t do email, so he would always kindly ask us to fax him the information. As a 22-year-old who grew up in the world of email, the fax machine was foreign to me. But I had to learn. How could I not?

Nat cared deeply about ��֭����’s work and fashioned himself a muckraking journalist. As a student at Northeastern University, he was fired from his editorship of the student newspaper by the president of the university for the paper’s critical coverage of the administration. When he later received an award for getting all As in his classes, the university president refused to attend the award ceremony. “I thought that was a tribute,” said Nat. In 1985, he received an honorary law degree from his alma mater.

He moved to New York City in 1953. In the towering career that followed his years as a “,” he wrote dozens of non-fiction books, novels, and memoirs. Nat interviewed some of the 20th century’s most prominent cultural figures, including Malcolm X, Che Guevara, and Bob Dylan, of whom he wrote one of his most famous profiles for . He also counted and among his friends (the latter friendship he lost after a negative review of Miles’ album Bitches Brew).

Nat’s seemingly disparate passions for the Constitution and jazz music weren’t so different in his eyes. Jazz percussionist and composer Max Roach once told him, “You know, you write a lot about the Constitution. What do I think we do? What we do in jazz, we are individual voices, right? Have to be. And we come together, and that voice is different and sometimes larger than the sum of the parts. Isn’t that what you’re talking about?”

In 1992, he published , which remains a classic defense of free speech even to this day. The central idea of his book, “free speech for me but not for thee,” became a meme in free speech circles. One might say that it’s an idea Nat spent his entire career fighting against. As a Jewish atheist, he went so far as to take to the barricades in defense of the right of Nazis to march on the city of Skokie, Illinois in 1977.

Nat leaves behind a tremendous body of work for young First Amendment activists like me to turn to as we seek to understand our heritage of free expression and the pioneering activists from “the old guard” who gave that heritage its richness.

His memoir, , is as good a place as any to start learning about his life. As is David L. Lewis’ 2014 documentary, “,” which explores Nat’s lived ideal of “free expression as the defining characteristic of the individual.”

While for me, and many like me, Nat’s most important work will always be his writings on the Constitution, for him, .” On one special occasion, Billie Holiday with saxophonist Lester Young.

“Billie and Lester had been very close, but they drifted apart,” Nat told NPR about the appearance. “They were talking to each other in their music, and they were looking at each other in a way that made you feel that, well, like you were in something that was a very private space and time. And that section was so utterly moving that in the control room, all of us had tears in our eyes.”

“After the show was over, I went down to the studio, and Billie came running after me and gave me a big hug, biggest prize I ever got,” he continued. “Robert Herridge [the producer of the show] got a letter a couple of days later from a woman saying it's just wonderful to see people doing what they love to do.”

We at FIREcouldn’t agree more with the woman.

Rest in peace, Nat. You spent your life doing what you loved to do.

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For more on Nat’s life and passions, and his friendship with ��֭����, check out with him at his Greenwich Village apartment (a transcript is available at this link):

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