Mike Bloomberg was preparing for the biggest role of his life, and he figured he needed some animators.
Four years after Donald Trump transitioned from the Apprentice boardroom to the Oval Office, Bloomberg assembled a team to market himself as the real Manhattan billionaire. Although Bloomberg is much richer than the president of the United States, he is far poorer in celebrity status. Trump spent decades fashioning himself into everyone’s idea of a spectacularly successful CEO. He was the definition of mainstream: In addition to firing people on a network TV show, he worked the ring with a microphone on WWE and obsessed over his treatment on Saturday Night Live, his city’s populist cultural institution. Bloomberg owned a little-watched financial network dominated by Wall Street wolves. At Trump’s news conferences, he’s always the biggest star, while Bloomberg could fade so far into the backdrop that he was once overshadowed by a viral sign-language interpreter. If Trump is an actor, Bloomberg’s a director/producer.
So, as he set out to build his audacious presidential campaign, Bloomberg knew he would need to become far better known to Americans. His internal polling showed that while voters might be familiar with the name “Bloomberg,” they’d absorbed little about his biography, his record as New York City mayor or his motivations for wanting to oust Trump from the White House. Bloomberg, with his limitless cash, would need to do in a few months what Trump had done over many years. So, when the time came to handpick his image makers, Bloomberg turned to the only guys he knew who could possibly do what had never been done: Bill and Jimmy.
Bill Knapp, a veteran ad maker and media strategist who held senior roles in three Democratic presidential campaigns and was part of the ad team on a third, planned to spend the election at home in Washington working on down-ballot races. Jimmy Siegel, who took a step back nearly 15 years ago from an advertising career in which he dreamed up commercials for Pepsi, Visa and Schwab to write thrillers and make TV ads for politicians, should be preparing for the release of his sixth novel. He was finishing edits when Bloomberg’s team called.
Together, the two men are now the creative heartbeat of the biggest advertising cannonade in presidential history. Before he arrived on the debate stage last week in Las Vegas, Americans were getting to know—and even like—the Mike Bloomberg they met in 30- and 60-second intervals between Jeopardy! questions and spins of the Wheel of Fortune. Behind more than a half-billion dollars in ad spending, the campaign worked better than basically all of Washington imagined it would. It helped vault Bloomberg into second place in some national polls, and into serious contention in Super Tuesday states, presenting him as the competent anti-Trump in places most Democrats had yet to air commercials of their own. Bloomberg’s bet on Bill and Jimmy seemed to be paying.
But then Bloomberg showed up in Vegas. That night, when the pent-up frustrations of his rivals all landed on his chin, Bloomberg shuffled off the stage having failed to match the management avatar they built up over nearly three months on the air. He recovered marginally on the debate stage Wednesday in Charleston, S.C., elbowing Trump while landing an early zinger on Bernie Sanders over reports that Vladimir Putin’s Russia was interfering in the election on his behalf. But the debates have laid bare the chasm between the controlled, even polished Bloomberg that viewers saw during commercial breaks and the stilted, prickly campaigner who took a pounding from Elizabeth Warren.
Interviews with more than a dozen Bloomberg advisors and allies shed light on the personalities and process behind perhaps the most unusual advertising campaign in American political history. If Bloomberg can bounce back on Super Tuesday from his Vegas debacle, he could change the rules of American presidential politics forever. And he’ll owe a big piece of his recovery to Knapp and Siegel, the guys behind his half-billion dollar curtain.
“Bill is an extremely focused, strategic thinker whose ads reflect an enormous amount of political expertise and cut to the chase,” said Howard Wolfson, a top adviser for Bloomberg who oversees the campaign’s sprawling paid media effort. “Jimmy is an immensely creative, gifted storyteller, and he has the ability to sort of really touch the heartstrings with his ads. They work very well together, and their styles are very complementary.”