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Michael Bloomberg, the man who believed he knew what New York needed, prepares to step down - but had he lost touch with the people of the city?

As the billionaire mayor of the Big Apple prepares to step down tomorrow after an unprecedented three terms in power, David Usborne examines Michael Bloomberg’s deeply contested legacy

When strict nanny finally packs her bags to leave, the children of the house are likely to react in different ways. Some will be glad to see her go and dream of midnight feasts while others will be nervous. Who’s going to keep the train set running on time now?

Even some fans of Michael Bloomberg, who pre-politics made billions selling financial data to Wall Street, will concede that, as mayor of New York City since 2002, he may have overstayed his welcome just a tad. It was he who forced a change in the law that allowed him to remain top of the roost for a third term. Had he gone when he was meant to, his reviews, now that his time is finally up, might have been kinder.

Still, they surely won’t be bad. The nanny moniker was born of his crusades on better health issues. They grated with some but have been rewarded with data showing that New Yorkers live longer than they used to when he took office (lower murder rates may have something to do with it, too). The city’s physical health has also been improved, with gleaming waterfront parks, bike paths a-million and lots of new trees.

To understand how long it’s been, consider that he took over in the immediate aftermath of the 9/11 attacks, when Gotham was reeling. Most high-schoolers here don’t remember a time when he wasn’t in charge. His first major health-related move was to ban smoking in restaurants and bars. The fuss it caused was monumental but today it seems about as controversial as outlawing trans-fats in commercial kitchens. He did that as well.

There were misfires and parts of his legacy remain deeply contested. On the one hand, he successfully rezoned about a fifth of the city for new development, created new forces of gentrification, expanded the tax base, attracted hoards of new tourists and doubled down on the crime-beating achievements of his predecessor Rudy Giuliani. But he failed in his bid to host the 2012 Olympics, saw another of his health initiatives – taking oversized fizzy drinks bottles off the shelves – overturned, and was thwarted when he tried to emulate London in bringing in a traffic congestion charge. On policing, he was roundly rebuked by a judge earlier this year who declared the NYPD’s notorious stop-and-frisk tactics unconstitutional.

Harder to enunciate, however, is a general sense that technocratic Bloomberg lacked not just charisma – never his strong point – but empathy, too; that, towards the end, he lost touch with the city’s traditional instincts for compassion and community. That the political pendulum had swung against him first became clear in the race to replace him. His favoured successor, Christine Quinn, New York City Council speaker, crashed spectacularly in part merely because of her association with him. Nudging her into the hard shoulder was Bill de Blasio, whose ultimately victorious campaign rested on a powerful “tale of two cities” message.

Therein resides the direst downside to the Bloomberg years. While he restored New York’s capacity for wealth creation he also oversaw a time of growing income inequality. That perhaps shows up most vividly in the city’s unresolved housing crisis and what he has said about it. Anyone living in Manhattan can see the problem has grown; the pavements are crowded with human encampments. Then there are the statistics.

Upon taking office, he vowed to cut homelessness by two-thirds in five years. It has grown by 60 per cent. What, a reporter asked him this month, did he think of the plight of one particular 11-year-old homeless girl profiled in The New York Times? “That’s just the way God works,” he replied defensively. “Sometimes some of us are lucky and some of us are not.” New York has many shelters that Mr Bloomberg says he has made better and nicer. But he has also passed rules making it harder to get into them.

The stop-and-frisk squall is more opaque. Bloomberg has been dogged in his defence of the practice whereby police regularly detain individuals and search them if they think it might avert a crime that has not in fact been committed. It has made New York safer, he says. But civil rights campaigners call it an abuse of power that is punitive to those stopped most often who are not whites but blacks and other minorities. They are put upon and trust between them and the police is destroyed. Mr de Blasio has vowed to end it.

Formerly a Democrat who became a Republican to run for the office in the first place, only later to become an independent, Bloomberg has never been easy to pigeon-hole. Liberals tempted to decry his capitalist compass nevertheless applaud him for his relentless anti-gun campaigning, his democratic style of running the government (he created a trading-floor atmosphere in City Hall, demolishing his walled-in private office in favour of moving his desk in with everyone else’s) and his unwavering support of gay and women’s rights. His philanthropy, for instance in fighting HIV, is unimpeachable. Likewise, Republicans find as much to hate as to like. No wonder there were several attempts on the national level to draft him as the man best able to break the two-party stranglehold and run for the White House as an independent.

Bloomberg, now 71, with homes on the Upper East Side, in Bermuda and London, never chewed on that piece of dubious chum. Instead, he forged on here for his full three terms. He leaves behind the High Line, a park on an old elevated train track that has become one of the city’s top tourist destinations, and a city hobbled after 9/11 that now hums. Some of what he wrought has still not come fully into being, like the huge development that will soon rise over the rail yards on the west side of Manhattan, the extension into the area of the Number 7 subway line and the construction of a whole new line up and down 2nd Avenue.  Eventually, of course, the city will also have a newly made World Trade Centre.

“We still face great challenges and we always will,” Mr Bloomberg said in one of a series of valedictory speeches before Christmas. “But I think it’s fair to say that we have never been better positioned to meet those challenges.”

The man tasked with taking them up after 1 January will be Mr de Blasio, who will be sworn in by former president Bill Clinton. Mr de Blasio’s approach will be different, but he’ll surely borrow from Michael Bloomberg a good deal if he wants to keep the house in order.