It never stopped being surreal, the contrast of the high-production-value Bloomberg show—full of slick PowerPoint presentations and glossy highlight-reel videos—with the sweaty, scruffy hustle of everyday New York politics. Sometimes the effect was comic, as when Bloomberg would don a bubblegum-pink sweater to march in the Pulaski Day parade. More often the culture clash was jarring: The multibillion-dollar-man piloting his own sleek $4 million helicopter into Albany, the capital not just of the state but of the shiny-suited, self-interested old politics that Bloomberg disdained.
The mayor’s first deputy mayor of economic development was Dan Doctoroff, who’d made millions as an investment banker in the eighties and nineties, then became a proselytizer for bringing the 2012 Olympics to New York, which is how he met Bloomberg. Doctoroff’s impact on the city outstrips even Burden’s, and much of his success flowed from a stinging defeat. The Bloomberg administration got more from the State Legislature than is commonly recognized, but Albany denied Bloomberg congestion pricing and a $2.2 billion West Side stadium. The mayor’s bitter analysis is that his proposal for the stadium, a centerpiece of the failed bid for the Olympics, was thwarted by Sheldon Silver, the State Assembly speaker, who killed the idea to protect his lower-Manhattan district from competition, and Jim Dolan, who didn’t want a new entertainment mecca competing with Madison Square Garden. But in a warped way, the death of the stadium was an assertion of democracy by Albany.
To Doctoroff, now president and CEO of Bloomberg LP, the stadium debacle demonstrated Bloomberg’s best qualities, his loyalty to staff and his imperviousness to political pressure. “We were bidding for the Olympics, and Cablevision was so aggressive in fighting it, at a time when he was gearing up to run for reelection in 2005,” Doctoroff says. “I went to him and said, ‘Look, if the cost of pursuing the Olympics bid is that you are not going to get reelected, then it’s not worth it.’ And Mike looked at me sort of with this anger in his eyes that I’d rarely experienced and said, ‘I don’t ever want to hear you say that again. We got into this together, it was the right thing to do, we’re gonna see it to the end.’ About a month later, the stadium went down to defeat. The only thing he said to me was, ‘Okay, so what’s Plan B?’ ”
Part of the answer is Hudson Yards, which is shaping up to be the quintessential expression of Bloombergism: big, expensive, highly manicured, with a fine-arts sheen and serious insider connections—Doctoroff is chairman of the board of the mini-city’s Culture Shed arts organization. The development is another marker in the spiraling cost of living here. The Democrats running to succeed Bloomberg have made affordability and income inequality central campaign issues, but the architects of Bloomberg’s development strategy don’t believe there was ever any choice.
“I think the notion of a split is simplistic and unfair,” Doctoroff says. “Six percent of the population of the city is now living in housing that they otherwise wouldn’t have been able to afford in basically every neighborhood in the city. That’s not to say gentrification doesn’t have negative consequences. It’s the ability to generate those additional revenues from growth that makes the good things possible; that’s a virtuous cycle. I don’t see anyone running for mayor who basically thinks about that, about generating marginal revenue—instead, it’s all about what we have to do in order to deal with the compassion problem.”
This is the heart of Bloomberg’s operating philosophy: something between noblesse oblige and trickle-down, coupled with a genuine desire to see hard work rewarded. And it’s what’s made the mayor’s reign brilliant and exasperating. Bloomberg won in 2001 because he seemed the right man for the post-9/11 moment: a self-made billionaire from the financial sector who could attract jobs and competently manage city government as New York grieved and fought back. His skills, connections, and experience were perfectly suited to rebuilding the city’s economy.
“Even before he was sworn in as mayor, Mike called the CEOs of companies and said, ‘I will guarantee you that we will do everything possible to try and make sure you are free from another terrorist attack,’ ” says Kathy Wylde, president of the Partnership for New York City, the big-business group that’s been an important Bloomberg backer. “And they made huge decisions on their companies and their companies’ lives based on that phone call. They would have never believed that from a politician, but they knew he was going to make decisions on the same logical basis that they do. He is the only person—the only mayor—with the credibility to do that.”