The mayor’s instinct for hiring creative thinkers and outsiders to run major agencies has usually served him well—from housing boss Shaun Donovan to Transportation Commissioner Janette Sadik-Khan and development chiefs Seth Pinsky and Bob Steel. But when Bloomberg replaced Klein, the mayor’s hubris undermined his own cause—choosing the disastrously overmatched publishing executive Cathie Black as schools chancellor shredded most of the goodwill he had left with parents. The fight over the results of education reform will rage for at least the next twelve years. There are more good schools than there were in 2002; graduation rates are up. The mayor has brought energy and money to neighborhoods like Brownsville and Mott Haven where schools had languished for decades. Yet there’s also been a continuous, destructive churn, and many of the kids who are toughest to educate are still stuck in dysfunctional schools. And cynicism about the letter grades assigned to schools is so deep as to make the innovation practically meaningless. The real impact of Bloomberg’s school reform, however, will play out as the generation of teachers hired in the past twelve years becomes the core of the classroom staff. It’s a group raised on constant numerical evaluations and iPads instead of lifetime tenure and chalkboards. All they’ve known is the Bloomberg way—and they will determine how much of the change is permanent.
Bloomberg’s choice for police commissioner was much more of a known quantity. Ray Kelly, after years of rising through the NYPD ranks, had served briefly in the job under David Dinkins. The mayor certainly wanted the city to become safer, as a condition for its economic success as much as anything else. But the operational details of NYPD policy weren’t a fixation at the outset of his administration.
Now, though, Bloomberg is vehemently defending his Police Department’s tactics, and his stubbornness is eroding what should be a prime part of his legacy, the plummeting homicide rate. The mayor’s June statement that “I think we disproportionately stop whites too much and minorities too little” wasn’t merely tin-eared; Judge Shira Scheindlin cited it to support her August decision declaring the NYPD’s implementation of stop-and-frisk not merely unconstitutional but racially discriminatory. “For Mike Bloomberg, it’s like, ‘Well of course what I’m saying is true,’ ” a mayoral ally says, wincing. “But for you and I, the hair on the backs of our necks is standing up. When it comes to thinking what we need to do, how do you weigh these big things—he takes his own logic and builds these incredible systems that lead to incredible results. But when it comes to the one-on-one, thinking about people—he’s probably one of the worst mayors.”
One great Bloomberg paradox is that even as the mayor developed a deeper feeling and appreciation for New Yorkers as individuals—much of it through tragedy, such as the hours he spent in hospital emergency rooms comforting the widows of cops and firefighters injured or killed in the line of duty—he increasingly treated the citizenry as data. So the New York City Marathon, a week after Hurricane Sandy, needed to be run to bring in more tourism revenue. During his first campaign, the mayor made an offhand remark suggesting that sanitation workers had the most dangerous city jobs. This, naturally, infuriated cops and firefighters. Bloomberg not only didn’t backtrack or amend his comments—a dozen years later, he was telling aides how the most recent statistics proved his point all over again.
It isn’t mere tone deafness with Bloomberg; it is a system of belief. “People think Mike’s a dick,” a top adviser says. “And he revels in it.” That attitude freed him to do great things for the city. But Bloomberg’s allergy to political and public friendship could also be the flaw that keeps his legacy from being even greater.
“I think Mike Bloomberg is an incredibly well-meaning person,” says a New York Democrat who has both clashed and cooperated with the mayor. “I think he wants to help people and make the world a better place—and there are a helluva lot of billionaires who don’t. But I don’t think he has the emotive ability to understand what other people are thinking, or has any desire to. It’s funny to me, because he was supposed to be this great salesman. He’s a terrible salesman. He doesn’t get other people.”
It’s a truism that Bloomberg’s money enabled his election and allowed him to float free of the warring interest groups that have traditionally dominated New York politics—but the effect of his wealth has been more far-reaching than has often been apparent. Less easy to chart than his donations to candidates, and more important, have been the funds he’s created to supplement city agencies with private dollars, everywhere from the school system to Governors Island. In 2010, Bloomberg raised millions of dollars for Education Reform Now, the lobbying group that pushed successfully to raise the state cap on charter schools. A new quasi-governmental technology-development project, funded mostly by private donations, is contracting for digital experts outside the civil-service salary structure who can untangle the city’s conflicting computer systems.