Alfred Flechtheim, the German collector, art dealer, and publisher, was a shadowy but significant figure in Ernest Hemingway’s life. Hemingway knew him at the peak of his prestige, influence, and fame, but lost contact when Flechtheim was overwhelmed by tragedy.

Flechtheim was born in Münster in northwest Germany in 1878, the scion of a wealthy Jewish family who—like the Buddenbrooks in Thomas Mann’s novel—had been grain merchants for several generations. He began work in his father’s business, but was soon drawn to modern paintings. “There is something crazy about art,” he declared. “It’s a passion stronger than gambling, alcohol, and women.”

Flechtheim exhibited works by Impressionist and Post-Impressionist artists before they became fashionable and...


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