Donald Trump, Michael Bloomberg, Howard Schultz: all three of these billionaire-politicians began their careers in that semicivilized field of aggression known as sales. Schultz sold Xerox copiers in midtown Manhattan, pounding pavements and making fifty cold calls a day. Bloomberg cut his teeth as a securities trader at the Wall Street firm of Salomon Brothers, where, as one of his former partners put it, you had to come to work “ready to bite the ass off a bear.” And Trump, of course, peddled lifestyle fantasies in the form of “prestige” real estate high in the sky.
They worked so hard, these strivers, and all three have told us many times in many ways that they have lived the American dream. Underlying their shifts from commerce to politics is the premise that the skills one develops in business translate more or less directly to the political realm. Trump is a case in point, demonstrating in the White House the same executive flair he showed in managing his Atlantic City casinos. Similarly, the competence Bloomberg displayed in building Bloomberg LP from “four guys and a coffee pot” to a multimedia empire with $10 billion in revenue has neatly carried over to politics. During his three consecutive terms as mayor of New York (2002–2014), the city became greener, safer, and healthier. The public schools, long a disaster, showed marked improvement. He led the city through the aftermath of September 11 and the financial crash of 2008, and balanced the budget in good times and bad.
In 2008, 2016, and again in the current election cycle, Bloomberg mounted what were perhaps the most strenuous—almost certainly the most expensive—presidential noncandidacies in American history. By late last year, he had his core team and a sophisticated data operation in place for a 2020 run, and was making campaign-style appearances across the country. Politico reported that Bloomberg’s “Plan A” for 2020 envisioned him running for president as a Democrat, while under “Plan B” he would participate only as kingmaker, deploying his considerable resources—staff, data, campaign infrastructure, as well as his heavy checkbook—on behalf of the eventual Democratic nominee. In early March he opted for “B,” and has vowed to spend a “floor” of $500 million to prevent a second Trump term.1
Schultz, like Trump, has eschewed entering politics at the subpresidential level. Only the top job is capacious enough for his vision, a display of hubris seemingly at odds with his belief in humility as an essential component of effective leadership. The rancor that greeted the launch of his precandidacy seemed to surprise him, but he has plunged on, dismissing concerns that his independent candidacy could be the spoiler that delivers a second term for Trump. Earlier this year, Schultz took the standard precandidacy step of releasing a new book, From the…
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