Like the jazz greats he admired, Nat Hentoff spent his career letting loose with long improvisations, but a typewriter was his instrument and sentences his melodies as he riffed through topic after topic, genre after genre.
Mr. Hentoff, 91, died Saturday in his New York City home while listening to Billie Holiday, his son Nick tweeted, and jazz was a regular refrain in his nearly three dozen books and decades of essays that also focused at various times on civil rights, education, politicians, religion, racism, and drug addicts.
Long associated with liberal politics, he told the Globe in 1993 that “if anything, I’m a lower-case libertarian.”
As a writer, though, he was most comfortable performing in the key of C – as in a capital C contrarian — taking pleasure in reconciling the irreconcilable. Mr. Hentoff began his career in Boston, as a Roxbury teenager writing about anti-Semitism, yet he defended cross burning as a form of free expression. He considered himself a feminist, yet opposed abortion and believed buffer zones around clinics violate the First Amendment. A 2013 documentary on his life was simply titled “The Pleasures of Being Out of Step.”
In 1992, he described himself as “a Jewish, atheist, civil libertarian, left-wing pro-lifer.”
The early part of his life was so formative that he called his first memoir “Boston Boy: Growing Up With Jazz and Other Rebellious Passions.” In 1953, he moved to New York City and spent a half-century writing for the alternative weekly The Village Voice, until he was laid off several years ago. Along the way he also wrote for magazines such as DownBeat and The New Yorker, for the Washington Post and The Wall Street Journal, and for numerous other publications. From his perch in New York, he occasionally contributed essays to the Globe, even taking a turn in the 1970s penning “The lit’ry life” column.
His many books and columns about civil liberties, primarily the First Amendment, turned Mr. Hentoff into one of the nation’s most recognizable defenders of the Constitution. He also was a sharp-toothed critic of the press and the media in general, decades before current concerns about fake news, propaganda websites, and day-to-day errors.
“I wonder how many of you are aware of how little checking goes on anywhere in journalism,” he wrote in the early 1970s. “I’ve written for a wide diversity of magazines and newspapers and only two of them fully check out the facts in a writer’s piece.”
Known principally as a New York writer, because of his lengthy perch at The Village Voice, he still considered himself a “Boston Boy.” In that 1986 memoir, he drew a thread between a story about eating a “salami sandwich in plain view on Yom Kippur” in his neighborhood and getting rejected several years later by Boston College. He imagined that, upon hearing about his failure, his Jewish neighbors would think: “That’s what happens to a boy who sits on the porch on Yom Kippur and eats a salami sandwich so that everyone on the way to shul should see him. You think God doesn’t write such things down?”
“It is not blasphemous to suggest that God might be pleased that Nat Hentoff has written such things down,” Martin F. Nolan, former editorial page editor of the Globe, quipped in reviewing the memoir.
Nathan Irving Hentoff was born in Boston on June 10, 1925. His parents, Simon Hentoff and the former Lena Katzenberg, were Russian-Jewish immigrants who lived in Roxbury.
Growing up in Boston, Mr. Hentoff sometimes faced vicious anti-Semitism and he seemed to notice nuances in everything he saw and heard. He likened Mayor James Michael Curley’s voice to a jazz cornet, calling it “a continuous astonishment. It was a vintage pipe organ and, like Buddy Bolden’s horn, could call in the voters from all the wards.”
Mr. Hentoff’s sixth-grade teacher insisted that he take the entrance exam for Boston Latin School, where “I learned that ceaseless hard work, however tedious … paid off,” he wrote in a 2001 essay for the Globe’s City Weekly. “Not only in the diploma, but in the realization that if you can make it at Boston Latin, you can make it anywhere.”
Not quite everywhere, though. He added that “having failed to meet the Jewish quota at Boston College (where, unaccountably, I wanted to major in Greek),” he graduated instead from Northeastern University.
Frances Sweeney, founder and editor of the mimeographed muckraking paper the Boston City Reporter, had given Mr. Hentoff a writing job when he was 15. At Northeastern, those muckraking skills drew the ire of the school’s president. Ordered “to cease all negative coverage of the university or leave,” Mr. Hentoff and most of his staff “proudly but sorrowfully departed. (It’s very hard to lose a byline).”
In college, Mr. Hentoff was already drawing notice in the Globe and elsewhere for his talents as a master of ceremonies for jazz performances, including at Boston’s Savoy Cafe. He also had a jazz program on WMEX-AM. “By the time I left Boston in 1953, the climate had grown warmer for jazz — there were thriving clubs, more airtime, more concerts,” he wrote in a 1976 Globe essay. “But jazz was still largely regarded in as a raffish and rather suspicious pastime.”
In New York, he was a regular at nightclubs, wrote for the jazz magazine DownBeat, and met musicians such as John Coltrane. Mr. Hentoff wrote the liner notes for Coltrane’s milestone 1960 album “Giant Steps.”
Along with writing about music and civil liberties, he published young adult books, novels, and magazine profiles, some of which he expanded into books. His bibliography includes “The Jazz Life,” “The Political Life: The Education of John V. Lindsay,” “Journey Into Jazz,” “John Cardinal O’Connor: At the Storm Center of a Changing American Catholic Church,” and “Free Speech for Me – But Not for Thee: How the American Left and Right Relentlessly Censor Each Other.”
Colleges sought out Mr. Hentoff as a lecturer, and he taught at places such as New York University and the New School. More than a dozen years ago, the National Endowment for the Arts recognized him as a Jazz Master, a rare honor for someone who wasn’t a musician.
He also was a senior fellow at the libertarian Cato Institute, where his biography says he was honored by the American Bar Association for his writings about criminal justice, the American Library Association for his defense of the First Amendment, and the National Press Foundation for his contributions to journalism.
Mr. Hentoff’s survivors and plans for a service were not immediately available.
His life course as a gadfly and an outsider may have been set in place on his first day at Boston Latin, when as a first-generation American he filed into the auditorium that seemed like a foreign land. “I was awed and intimidated by the names of previous graduates high on the walls: Cotton Mather, Ralph Waldo Emerson, John Hancock, Samuel Adams, George Santayana,” he wrote in the Globe in 2001. “What was I doing there – this child of Jewish immigrants, so despised by so many Bostonians?”