Hentoff, one of the nation’s foremost authorities on the First Amendment, had written for the Village Voice for over 50 years before he joined Cato in 2009. “Becoming a senior fellow of the Cato Institute — from whose publications I’ve often quoted — enables me to continue following the advice of my earliest mentor, Duke Ellington, who told me never to be caught up in a musical or any other category,” Hentoff said at the time. “Duke said that it’s always the individual’s expression that defines his identity. All these years later, if I had to describe myself, it would be as an uncategorizable libertarian — and that’s why I’m delighted to be at the Cato Institute, where freedom rings.”

Hentoff had a long and rich career — as a jazz critic in the 1950s he counted not only Duke Ellington among his friends, but many other jazz luminaries, and Malcolm X, with whom he marched for peace and racial equality. His column, Sweet Land of Liberty, was distributed by the United Feature Syndicate from 1992 to 2016, and he authored over 35 books — from novels to books for young adults to nonfiction works on civil liberties. He won numerous awards, including the American Bar Association Silver Gavel Award for his coverage of the law and criminal justice, the American Library Association’s Imroth Award for Intellectual Freedom, and the National Press Foundation Award for Distinguished Contributions to Journalism. In 1999 and 2002 he was a Pulitzer finalist for commentary.

Hentoff was never afraid to ruffle feathers — although he partnered with the left throughout much of his career, he was a frequent critic of censorship and political correctness on both the left and the right. He warned in 1991 that “A precedent has been set at, of all places, colleges and universities, that the principle of free speech is merely situational… . Once speech can be limited in such subjective ways, more and more expression will be included in what is forbidden.” Hentoff had personal experience with college censorship — he was forced to resign from the paper he edited at Northeastern University once he uncovered the fact that some college trustees had been funding anti‐​Semitic publications. Later in his career, his libertarian instincts increasingly irked his erstwhile allies on the left, and he was let go from the Village Voice in 2009. In his final column there, Hentoff joked that he would simply put on his “skunk suit at other garden parties.”

In 1957 he got an opportunity that he would forever name his proudest achievement: working as a producer for a television special called “The Sound of Jazz.” As his Cato colleague Tim Lynch recalled, “He jumped at the chance to bring beautiful jazz music into the living rooms of folks who had never really been exposed to it before.” One of the most famous performances from that evening was Billie Holiday’s rendition of “Fine and Mellow.” In 2000, Hentoff recalled that “after it was all over, she was so pleased with how it went — it was live, by the way — she came over and kissed me. And that’s worth more to me than the Congressional Medal of Honor.” When he passed away, his son reported that he was surrounded by his family, listening to Billie Holiday.