Boston and the surrounding area is rich in history, from the colonial era forward, and I appreciate all of it. But I am particularly interested in Boston in the 20th century, and have researched the middle years of that century extensively. My extreme interest in certain aspects of the city’s cultural history led me to form Troy Street Publishing as a vehicle for sharing ten years of research and writing.

The Boston Jazz Chronicles Cover
Click here to buy The Boston Jazz Chronicles on Amazon now.

My first endeavor was a seven-year labor of love, The Boston Jazz Chronicles, which I published through Troy Street in 2012. It was early in the self-publishing game and I thought the prospects and possibilities of that game were endless. I still do, and my goal is to publish the projects described elsewhere on this site.

This website, and its blog, The Troy Street Observer, are the primary outlets for telling my stories, but there are others—public speaking, walking tours, and a YouTube channel that puts some of the historic but out-of-print recordings back in circulation.

What’s in it for you? On this site you’ll find content about Boston people, places and events that you won’t find anywhere else. I’ve opened a window, and through it you’ll hear some of the not-so-common stories of Boston. Check back often to see what’s new.

—Richard Vacca

The Troy Street Observer

Nat Hentoff: Remembering a Boston Boy

“Whaddya need? I’m on a deadline.” Thus would begin my first phone conversations with Nat Hentoff, the jazz lover, journalist and self-described troublemaker who died in his New York City home on January 7, 2017. He was 91.

That was Hentoff’s standard gruff greeting, and all who heard it quickly learned there was no time for small talk. You asked your question, got your answer, and went on your way.


Nat Hentoff at WMEX, 1946. Photo by Red Wolf.

This changed when I asked him about Counterpoint, a newsletter that he wrote and produced in 1947. He asked how I learned about it, and I told him that the Dorothy Prescott Papers in the Library of Traditional Jazz at the University of New Hampshire had an almost-complete set. That got him started—Dorothy had been a good friend and fellow member of the Jazz Society, a group of enthusiasts who staged concerts in 1944-46. The long-forgotten Counterpoint carried me past the deadline greeting.

Nat’s claim to fame during his Boston years was an eight-year tenure with WMEX radio. He hosted both jazz and classical music programs in the studio, and remote broadcasts from the Savoy and Storyville jazz clubs. (His engineer on the remotes was Arnie Ginsburg, later known as “Woo Woo” Ginsburg, a Top 40 deejay.) Improbably, Nat also covered sports, announcing boxing matches from the Boston Arena. At Storyville, George Wein had Nat emcee the Sunday afternoon jam sessions.

Hentoff started his jazz show on WMEX in 1945 with a narrow point of view and a reputation as a moldy fig. By 1949 that had changed, and trumpeter Don Stratton claimed he heard Hentoff play his first bebop record. “It was “Parker’s Mood,” Don told me. “And after, Nat said, “Charlie Parker… he can really play the saxophone when he wants to.” We couldn’t believe it! Hentoff played Bird!”

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