Iowa was supposed to be make-or-break for Ron DeSantis. The Florida governor essentially moved his campaign there late last year, and Never Back Down, his allied super PAC, spent tens of millions of dollars knocking on doors in the state. “We’re going to win Iowa,” DeSantis declared on NBC’s “Meet the Press” on Dec. 2. But in the week before the all-important caucuses, Scott Wagner, the recently installed head of the super PAC, was doing something that aides found puzzling: He was literally doing a puzzle. In the headquarters of Never Back Down in West Des Moines, Iowa, Wagner was,...