The call came down last week to Barry Singer, 60, owner of Chartwell Booksellers in Midtown Manhattan — “The World’s Only Winston Churchill Bookshop” — from an executive upstairs in urgent need of a Churchill coffee mug. The mug request had Mr. Singer stumped. He told the caller to hold and disappeared into the rear of the store, a stately refuge of red carpet and carved oak book cabinets tucked in the public atrium of the Park Avenue Plaza between 52nd and 53rd Streets. In his 34 years running the shop, Mr. Singer has sold Churchill’s polo jodhpurs, signed portraits, and even Churchill’s discarded cigar stubs ($1,500 apiece). But mainly, he is a bookseller. At the moment he was shipping a copy of Churchill’s “My Early Life” ($1,500), as well as a portrait that had been signed by the former British prime minister during World War II ($11,000). The shop has had a good year, with the British statesman being portrayed in two recent films, “Churchill” and “Darkest Hour,” as well as in the Netflix series, “The Crown.” The store itself was even featured as a setting recently in the Showtime series “Billions.” But the holiday rush was providing some new challenges for Mr. Singer. Churchill died in 1965 at age 90, leaving an output of more than 40 titles and volumes that have been reprinted in some 8,000 different editions by now. There are also roughly 800 books about Churchill, said Mr. Singer, who added that he’s had a copy of all of them in the store at some point. His inventory ranges from a $10 paperback of “Churchill on Europe” to a 1906 first-edition softcover of “For Free Trade,” written by the man himself, and stored in a safe at the shop. It goes for a “negotiable” $185,000, Mr. Singer said. Rare editions of every title Churchill authored can be glimpsed on five shelves locked behind glass doors in the rear of the store: from a first edition of “The Story of the Malakand Field Force” ($5,500), to a signed volume of one of his final works, “A History of the English Speaking Peoples” ($6,500). The shop has hung on as one of the last independent bookstores in Midtown Manhattan partly because of Mr. Singer’s own Churchillian tenaciousness, and also because the skyscraper’s owners, the Fisher Brothers, have long extended a “favorable” financial arrangement to Mr. Singer, he said. “They have a certain affection for the shop,” said Mr. Singer, who, throughout the years, has certainly leveraged the spell that Churchill casts over certain rich and powerful men who admire his resolve and leadership. For example, following the terrorist attacks of September 11, 2001, Mayor Rudolph W. Giuliani bought copies of John Lukacs’ “Five Days in London: May, 1940” to lean on, Mr. Singer said. Caspar Weinberger, while serving as secretary of defense under President Ronald Reagan, bought a pile of books and told Mr. Singer to send the bill to the Pentagon, Mr. Singer said. Mr. Singer hails from Passaic, N.J. and attended Columbia University. He is the author of several books himself, and as a freelance journalist, has written for publications like The New York Times. His 2012 book, “Churchill Style: The Art of Being Winston Churchill” is on prominent display in the shop for $25, with signed first editions priced at $50. Mr. Singer said he had little interest in Churchill 35 years ago when he met Richard Fisher, a real estate mogul with an English degree and a desire to put a bookstore in the lobby of his Park Avenue skyscraper. Mr. Fisher named the shop after Chartwell, Churchill’s country home in Kent, England, but the store wasn’t devoted to Churchill, at first. Sales in the early days were slow, so Mr. Singer began printing up weekly newsletters highlighing various hardcovers, and sending them to the high-powered finance firms in the building. One week, he mentioned a few Churchill books he had acquired, which caught the eye of the financier Saul Steinberg, the corporate raider. Mr. Steinberg’s secretary called down to Mr. Singer requesting “a complete set of everything Churchill ever wrote, first edition and bound in leather,” Mr. Singer said. Mr. Singer wound up charging Mr. Steinberg $100,000 for the set, half of which was for a rare copy of Churchill’s “Mr. Brodrick’s Army.” “He got a bargain — it’s worth more now,” said Mr. Singer, who after his first year open, switched to a Churchill theme. Mr. Steinberg kept the set in his 34-room Park Avenue triplex and held on to it for emotional support, Mr. Singer said, even when his losses forced him to sell off many other assets. Mr. Singer reappeared from his office with a Churchill coffee mug, his personal keepsake, grabbed from his desk. “I have one for you,” he told the executive on the phone, a regular customer. “On the house.” The New York Times