Cecily Gemmell, the last surviving personal secretary to former British Prime Minister Winston Churchill, died on Thursday in New York City at the age of 97, according to her caretaker, Mary Pizzarelli.

Ms. Gemmell, affectionately known as Chips, began working with Churchill in the summer of 1947, shortly after his defeat in the 1945 general election. At 18, she joined a select group of young female secretaries who were tasked with the demanding role of transcribing Churchill’s speeches and correspondence. The position required significant stamina, as Churchill was known for dictating late into the night.

Her initial work involved cataloging Churchill’s extensive World War II papers at Chartwell, his country home in Westerham, where she was responsible for organizing the prime minister’s wartime records in preparation for his memoirs. She bicycled to and from Chartwell daily, navigating a steep hill, and worked primarily in the Minement Room’s semi-basement, a space where she had limited contact with Churchill’s notable associates, glimpsing only small personal details such as the foreign secretary Anthony Eden’s distinctive pink socks.

Ms. Gemmell’s first direct experience working with Churchill occurred one evening at Chartwell, where she recorded his dictations from a typewriter positioned on a card table beside his four-poster bed. She described the challenges of typing precisely as he dictated, often struggling to hear and understand him while coping with the mechanical demands of the typewriter. Despite initial nervousness, she found encouragement in Churchill’s warmth during their interactions.

Born on December 25, 1928, in Bangalore, India, Gemmell was the daughter of Col. Geoffrey Woodburn Gemmell, a map surveyor with the Indian Army. She received her early education at schools founded for British children in India before returning to England in 1945, where she completed her secretarial training at Mrs. Hoster’s Secretarial College.

In 1951, Gemmell resumed her duties when Churchill returned as prime minister, accompanying him to significant locations including the Cabinet Room at 10 Downing Street, racecourses, and international destinations such as Monte Carlo, Marrakesh, Lake Como, and the Dolomites. Churchill also took the rare step of painting a portrait of her, intending to gift it during Christmas at No. 10 Downing Street.

In 1953, Ms. Gemmell transitioned to working for Churchill’s wife, Clementine, before retiring from Churchill’s service that same year. She then moved to New York City, where she secured secretarial positions at Life magazine and later at Time Inc. Her social life in New York included frequent visits to jazz clubs, where she developed a relationship with pianist John Bunch, whom she married in 1998. Mr. Bunch passed away in 2010.

Ms. Gemmell’s tenure coincided with significant moments in Churchill’s career, including his knighthood in 1953. She recalled an encounter shortly after the honor was conferred, describing how she humorously addressed him as “Sir Winston,” to which he responded with quiet amusement.

With her passing, the last direct link to Churchill’s personal secretarial staff—an exceptional group that served the statesman from the early 20th century through his postwar years—has come to an end.