As the decade unspooled, though—a time of headlong technological change and wild financial swings—Bloomberg also became the almost too-perfect symbol of his own city. He was an up-from-the-middle-class product of education and hard work who struck it rich selling a digital breakthrough in the packaging of financial information to Wall Street. As tech reshaped society, and the financial industry assumed an outsize role in New York’s life, and the city’s income extremes grew wider apart, New York’s mayor happened to be a man who both cared about improving the city services most vital to the 99 percent—schools, parks, transportation—and was the very embodiment of the one percent. Shrinking crime to historic lows spared the innocent, but a safer city also attracted commerce; better schools produced more valuable potential employees, drawing still more new businesses. The means to those two ends were less important. Which is why two of the realms that touch millions of day-to-day New York lives have proved the messiest for Bloomberg. A traditional pol, rising from community board to citywide office, might be beholden to special interests—but also might be responsive to the grassroots. Because of who he is and what he believes, Bloomberg approached issues as an engineer bent on fixing systems, not as an elected official sensitive to the lives of actual people.
From his first campaign, Bloomberg asked to be judged on whether he improved the city’s schools. And the battle over how the city educates its young people is an object lesson in Bloombergism, in all its strengths and intrinsic flaws. Bloomberg finally won mayoral control because he was different from his predecessors in one pivotal aspect: He was on no one’s side. The State Legislature could rid itself of a headache without rewarding or punishing any of the many traditional actors in the education drama. Bloomberg was a free agent, arriving with no enemies and no real constituency, and it provided him, at the outset, with a rare reservoir of political trust.
Now that he was responsible for more than 1 million kids, however, Bloomberg needed to figure out what to do with them. As much as he believes in data, as much as he comes across as cold-bloodedly analytical, Bloomberg has often relied on instinct when selecting lieutenants. “We needed an education guy,” Sheekey recalls, “and Mike said, ‘Well, Joel Klein is a really smart guy. Why don’t we try Joel?’ ” In Klein, Bloomberg got a brilliant legal mind and a tenacious fighter—with perhaps more of the second quality than Bloomberg had bargained for. Relations with the teachers union started out fairly cordial, and the mayor’s awarding of substantial pay raises in advance of his 2005 reelection campaign certainly helped. But things deteriorated in the mayor’s second term as Klein’s top-down, test-heavy reforms aggravated parents and the UFT’s leadership changed from Randi Weingarten to the more combative Michael Mulgrew.
“Let me cop to this—I’m sure there are things I could have done better,” Klein says. “I could have reached out or whatever. But make no mistake about it, until we showed up, the union was the thousand-pound gorilla. Then the second group were the bureaucrats. In order to effectuate change, you have to go after those very powerful groups. This big change could not be done without a lot of noise and a lot of pushback.” And for most of Klein’s tenure, he knew Bloomberg had his back. “You can agree with Mike or disagree with Mike, but I do think he really cares deeply about policy and fights for things he believes in. He’s not the man in politics who holds his finger to the wind. He’s pretty much a guy who believed deeply that the system here was broken and that it was critical to the future of the city to fix it. He wanted somebody who wasn’t a careerist, somebody outside the system who has not grown up acculturated to it, who was more likely to have a chance to change it.”
Sheekey rues the errors that hurt those chances. “Two things we got wrong were how we define charters and how we define closing schools,” he says. “Unfortunately, a lot of charters get described as not public schools, which of course they are. That was the first mistake. And the second mistake was ‘closing schools,’ because we’ve never closed a school. Ever. We remove the principals and the teachers and replace them with new structures with the same children in the same buildings. That’s obviously not closure. But we screwed up the language, because communication wasn’t the concern; doing the right thing was always the concern. Communication almost seemed like capitulation.” Bloomberg’s education-reform goals—spreading quality education across the city, especially to poor neighborhoods—have been progressive and egalitarian, even when the methods—a mania for testing, the shaming of teachers—have been needlessly authoritarian.