The sun was shining, the breeze was mild. It was a beautiful Friday afternoon three weeks ago inside Carl Schurz Park, where two of Michael Bloomberg’s top political lieutenants waited for the mayor to arrive. They were killing time chatting about the glories of the New York City Marathon. Howard Wolfson, a deputy mayor and political strategist, had run the race twice, but injuries forced him to quit short of the finish line both times; Wolfson was mulling whether to take another shot at the full 26.2 miles in nine days. Bill Knapp, one of the country’s elite campaign consultants, grew up in the city but has long lived in Washington and hadn’t attended the marathon in years. Wolfson described what a grand, unifying, multicultural event the run had become—the best day, he believed, in the city every year.
Up walked the mayor, a smile on his face. Nine days before, Bloomberg had announced the creation of his very own super-PAC, with plans to spend up to $15 million to influence elections all across the country. Stricter gun laws and the legalization of gay marriage would be key issues, with Wolfson, on leave from City Hall, in charge and using all the tools of a modern campaign, including direct mail, Internet ads, and robo-calls. Those plugs would carry the opaque label of the super-PAC, Independence USA.
Bloomberg was in the park, three blocks south of Gracie Mansion, that day to shoot the only TV ad in which he’d appear on-camera, in support of Chris Murphy, a Democrat r...