Winston Churchill wrote in his History of the English Speaking Peoples (1956) that Henry V was the first king to unify the people of the British Isles around a common language. Henry’s masterful use of English, Churchill believed, rallied his troops to defeat the French at Agincourt and placed him, “and with him his country, at the summit of the world.”

Like Henry, Churchill understood the power of his native tongue in leading a nation through war. His own impassioned rhetoric “mobilized the English language and sent it into battle to steady his fellow countrymen,” the American radio broadcaster Edward R. Murrow said shortly after World War II. And those compelling speeches are often commented on and imitated: President John F. Kennedy singled them out as ranking among Churchill’s greatest achievements when granting him an honorary American citizenship in 1963.

But only one bookstore deals specifically in Churchill’s words: Chartwell Booksellers. Located in the lobby of a skyscraper on the corner of Fifty-second Street and Park Avenue, the shop sells all forty-two of Churchill’s books (many in rare or first editions), as well as a variety of titles about his life and career.

His first big client was the corporate raider Saul Steinberg, who ordered every published Churchill work in leather-bound first edition.

Chartwell is the pet project of Barry Singer, a former journalist and self-taught Churchillian. Singer opened the store in 1983 at the request of the building’s owner, Richard Fisher, an Anglophile who wanted to provide his high-profile tenants with a mid-day literary retreat. The two were social acquaintances, and in 1981 Fisher asked what Singer’s ideal bookstore would look like. Singer responded immediately: “A gentleman’s library with an English country house feel, an oasis away from the streets—and with all hand-carved bookcases.”

Fisher loved the idea and convinced Singer to open a bookstore modeled architecturally on London’s Burlington Arcade. Fisher also asked that Singer christen it “Chartwell Booksellers,” after Churchill’s country estate in Kent.

But in the store’s first year, it had no relation to Churchill outside of its name. Singer knew little about the famous prime minister and operated Chartwell as a general-interest bookstore. Soon, however, he realized the store would need more focus to thrive in midtown Manhattan. He had recently picked up several old Churchill books at a used bookstore, so he took out a small box ad in the New Yorker advertising his still-nascent catalogue. He also created a Churchill newsletter, which he distributed to the various offices throughout the Fisher building.

The ads were only an experiment, but the enthusiastic responses encouraged Singer to rebrand Chartwell as a hub for Churchillians. His first big client was the corporate raider Saul Steinberg, who ordered every published Churchill work in leather-bound first edition. Steinberg didn’t care when or how Singer got the books—he just wanted them.

Singer took the commission as an opportunity to fly to England, scrounge through London bookstores, and visit the original Chartwell—all the while learning about Churchill “on the fly”—before he assembled the complete collection. He repeated the process for many more clients, mostly accomplished businessmen with a keen interest in the Last Lion.

The interior of Chartwell Booksellers. Courtesy Barry Singer.

After thirty-six years in the business, Singer has yet to find another bookseller who traffics so heavily in Churchilliana.

“I still don’t know why,” he says.

But Singer does think he has an idea why Churchill has such enduring appeal among his wealthy clients.

“Churchill was a great statesman, a great writer, and a great warrior,” Singer offers; “but above all that, there was always decency in everything he engaged in.” Churchill’s example, he adds, often brings out the best in his readers: “He never worked just for personal gain, never just for his own ego. He always aimed at the greater good.”

For his own part, Singer says he’s particularly attracted to Churchill’s magnanimity, especially in the way he lived outside of the political sphere.

“He built this life that I think was very important to his equanimity, in that he could get away from public life and nurture himself and rejuvenate,” Singer says.

That life, with its painting, bricklaying, and smoking, became the subject of Singer’s own book, Churchill’s Style: The Art of Being Winston Churchill (2012), which focuses on the prime minister’s love of leisure. Those interests also sometimes work their way into Chartwell’s inventory, too. Over the years, Singer has sold the occasional Churchill painting or cigar butt.

“I think I’ve sold three or four cigar butts, ever,” says Singer. “Fundamentally, we’re a bookstore, and I think I’d rather just deal with the books.”

And as he has focused more on Churchill, Singer notes, Chartwell’s profile has risen. Although it used to be an outlet aimed mainly at devoted Churchillians, the recent successes of Netflix’s The Crown (2016– ) and the 2017 film Darkest Hour have broadened its customer base. The store has also been featured in Showtime’s Billions (2016– ), in an episode where one character’s financial woes force him to sell his Churchill collection at Chartwell. Singer says it surprises him how many people know the store because of Billions.

“It’s amazing how many people come from all over the world just to take selfies where what’s-his-name sold his Churchill books in the back of the store,” he says.

The store consistently attracts notable Churchillians, including direct relatives of the prime minister and the actor Gary Oldman, who played Churchill in Darkest Hour. Chartwell also hosted Boris Johnson when he released his biography, The Churchill Factor: How One Man Made History (2014), as he has done for various other notable authors.

For Singer and his patrons, it’s Churchill’s own words that keep them coming back. Singer recalls how after Steinberg lost a large chunk of his fortune in the early 2000s, Chartwell’s first major client “sold his master paintings, sold his Titians,” but told Singer: “I’m keeping the Churchill books, because they give me consolation.”

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