On the morning of November 2, 1948, as voters headed to the polls to choose between the incumbent Harry S. Truman and New York governor Thomas E. Dewey for president, the Chicago Daily Tribune’s Washington bureau chief, Arthur Sears Henning, had already begun his story for the next day’s papers.

Based on polling results, he named Dewey the victor, and later that evening, in the midst of an ongoing printers’ strike (which necessitated an earlier press deadline), the Trib’s editors backed up Henning’s prediction with an eight-column headline: “Dewey Defeats Truman.” By midnight, when editors changed the headline, about 150,000 copies of the paper had gone out.

The next day, as a victorious Truman traveled by train from Missouri to Washington, someone put a copy of the paper into his hands at a stop in St. Louis. Grinning broadly from the train’s back platform, Truman held it aloft, and Frank Cancellare, the White House photographer for United Press International, snapped the picture. Said Truman of the headline, “This is one for the books.”

Chicago has inspired countless memorable photos. Cancellare’s photo of Truman is among the ten most famous images of the city in our December photo issue, on newsstands now. Check the magazine for more captivating shots, including Unseen Chicago, an 18-page portfolio of rarely seen pictures of the city.

Check chicagomag.com often for more features from our photo issue, including a camera buying guide and a timeline that tracks the parallel course of photography and the city.