If you go looking for Chartwell Booksellers, you may find yourself walking in circles around a Midtown block. 55 East 52nd Street is home to the investment company Blackrock, with a large indoor privately-owned public space on the ground floor. You’ll see a pleasant waterfall, a Starbucks, maybe you’ll cross the public space and find yourself on 53rd Street. But, on a wall opposite from all the buzz is a sign in a royal red color with an arrow: “CHARTWELL Booksellers. The World’s Only Winston Churchill Bookshop.” Follow it behind the elevator banks and discover a handsome store with curved window displays and wooden bookshelves, and a lot about England’s most famous prime minister.

Last month, Chartwell Booksellers celebrated its 36th anniversary. It was founded by Columbia University graduate Barry Singer on the request of real estate magnate Richard Fisher, who owned the skyscraper along Park Avenue. Fisher had an English degree and shared a predilection for Churchill, like many others of the world’s 1%. He named the shop after Churchill’s country estate in Kent, England where he lived for over forty years. While this obsession may not be as well known to us plebeians, it has been fictionalized in the popular television show Billions on Showtime. One of the central characters of the show, New York District Attorney Chuck Rhoades finds himself short money with his funds tied up in a blind trust, so he sells his collection of Winston Churchill books to Chartwell Booksellers. One of Chuck’s books comes with an inscription to General Montgomery and an autograph. His nemesis, financier Bobby Axelrod instructs his new chief of staff to buy up Chuck’s collection, along with all the collector books he can get on Churchill.

And indeed, Chartwell Booksellers sells a wider range of Churchill wares, from rare first editions of some of the forty books Churchill wrote himself to collectible Royal Doulton figurines. Then there are the approximately 800 books that have been written about Churchill, including one by Singer entitled Churchill Style: The Art of Being Winston Churchill, along with other new books about World War II and global statesmen and women. Michelle Obama’s Becoming was in the window on our visit, and The Crown, the Robert Lacey biography upon which the Emmy-award winning Netflix series of the same name was based upon was in the “New/Noteworthy” section. Lynne Olsen’s latest book Madame Fourcade’s Secret War, was also on display, another one of the author’s absorbing books about World War II uncovering stories more incredible than any in fiction or film. 

In 2017, Singer told the New York Times that he did not have any expertise in Churchill when he first started, but when financier Saul Steinberg requested a first edition of everything Churchill ever wrote, he realized the value in “streamlining his inventory.” He spent a few years traveling through England and “learned about Churchill on the fly.”

Chartwell prides itself in having the largest collection of rare Churchill first editions, books, and even signed letters from Churchill himself, but Chartwell Booksellers also carries a collection of books focused on topics such as the military, photography, jazz, art, motor, children’s books, and even literary collectibles worth up to $5,000. We were particularly pleased to see William Low’s Old Penn Stationbased on our own obsession with the original Penn Station.

Located on Chartwell’s website catalogue of the contents of Chartwell Booksellers along with prices for interested collectors. There is also a “Collector’s Guide” for those who are just beginning to start gathering their collection of Churchill memorabilia. Singer runs a blog Churchill Style completely devoted to everything about Winston Churchill from his fashion sense to the brand of cigars he smoked that is based on his own book Churchill Style.

Chartwell owner Barry Singer’s autographed book, Churchill Style: The Art of Being Winston Churchill

Chartwell Booksellers is one of the few remaining independent bookstores in Midtown Manhattan, proving that specialization is key in today’s market (and having a landlord who supports your cause). Chartwell Booksellers is located in the lobby of the Park Avenue Plaza Building at 55 East 52nd Street in Midtown and is open Monday-Friday, from 10 AM to 6 PM.

Next, check out 10 of NYC’s Independent Bookstores and read about The Lit. Bar, the Bronx’s First and Only Independent Bookstore.