Edward Greenwood liked to play solitaire on his work computer. One day in January 2006, the 39-year-old stepped away from his desk in the middle of a game. When he came back, it was too late: the boss had caught a glimpse of the screen. Greenwood got the sack. Normally it doesn’t make the papers when an unknown person gets fired from a $27,000-a-year office job. This time it did. Greenwood’s boss was New York City’s no-nonsense mayor, Michael Bloomberg, and his job was in the city’s Albany lobbying office.

The local media ate it up. MAYOR BLOOMBERG DOESN’T LIKE GAMES, sniffed Gothamist.com. Some New York Post readers called it an overreaction; most said that Greenwood had it coming. “We pay city employees to do the work that the public expects done,” Bloomberg said. “The workplace is not an appropriate place for games. It’s a place where you have to do the job that you’re getting paid for.”

It was vintage Bloomberg: decisive, pragmatic, concise. Then beginning his second term as mayor, the self-funding tech billionaire was hitting his stride as a political leader. New York in 2006 was as safe and prosperous as it had ever been. Building on the remarkable public-safety gains of his Republican predecessor, Rudy Giuliani, Bloomberg’s NYPD had pushed crime down to unimagined lows. He’d gained control of city schools—a goal that had eluded previous mayors—and introduced choice and accountability into a notoriously sclerotic, union-dominated system. He preserved welfare reform and did his best to get a handle on the city’s skyrocketing pension obligations to its retired workers. The city’s parks and public spaces flourished; so did its arts scene and philanthropic sector. Tourist money juiced the city’s economy, which enjoyed record-smashing job growth. Brooklyn became internationally known as a synonym for urban revival led by the creative class.

In November 2005, the New York Times called Bloomberg’s 20-point reelection victory over Bronx borough president Fernando Ferrer “a triumph of competence over the ideology, ethnic politics, and partisan appeals.” Along with Giuliani, the Times said—grudgingly, one imagines—Bloomberg had “set a standard by showing that voters across party lines want a commanding and independent-minded mayor who shows measurable results on crime, education and quality of life.” Bloomberg was a true independent. His vast wealth meant that he was beholden to no one. He could say what other politicians refused to say and do what others refused to do. This included his unpopular decision to ram through an extension to the city’s term-limits law so that he could run for a third term in 2009. He cruised to victory over Democratic city comptroller Bill Thompson and cemented his joint legacy with Giuliani as the men who saved the city.

It seems all but certain that Americans will wake up Wednesday morning to strange and, to some, frightening New Hampshire primary results. The Republicans will have selected the bombastic populist Donald Trump; the Democrats will have chosen the avowed socialist Bernie Sanders. Sensing an opening for a pragmatic centrist in the general election, Bloomberg has confirmed that he is exploring an independent run for the White House. His decision will likely hinge on what shape the race takes over the next several weeks.

Reactions range from bemusement to open hostility. Conservatives especially will gag on the idea of supporting an anti-gun, nanny-state mayor who supports same-sex marriage and abortion rights. But many of Bloomberg’s most meddlesome initiatives—like his infamous attempt to ban “big gulp” soft drinks—came to nothing. The ones that did become policy—like the 2003 indoor smoking ban—seem hard to argue with in retrospect.

On issues ranging from crime to education to economic growth, Bloomberg governed like a conservative. On one issue especially, his record stands up to any leader in America: terrorism. In 2011, the Associated Press published a series of 30 articles claiming that in the years since 9/11, Bloomberg’s police commissioner Ray Kelly had built “an aggressive domestic intelligence program” that had “systematically spied on Muslim neighborhoods, listened in on sermons, infiltrated colleges, and photographed law-abiding residents.” Bloomberg stoutly defended Kelly and the NYPD Intelligence Unit. “We live in a dangerous world, and we have to be very proactive in making sure that we prevent terrorism,” Bloomberg said. “[I]f you’ve got a clergyperson preaching anarchy, do you really think the police department shouldn’t try to send somebody and listen and see if they’re trying to foment a riot? You can’t wait till the riot’s on the streets.”

Bloomberg refused to back down, even when bigshot liberals like Yale University president Richard C. Levin accused the NYPD of violating American values by monitoring the websites of Muslim student groups. “The Police Department goes where there are allegations, and they look to see whether those allegations are true. That’s what you would expect them to do. That’s what you would want them to,” Bloomberg fired back. “We have an obligation to do so, and it is to protect the very things that let Yale survive.”

Bloomberg may not look like the ideal candidate for loyal Democrats or conservative Republicans, but his candidacy could prove compelling in a topsy-turvy election year like this one. As a pro-growth, pro-education reform, pro-Israel candidate, and as a government executive who expects public employees to earn their pay, Bloomberg could have broad appeal to the anti-Trump wing of the GOP. On the center-left, a pro-choice, pro-gun control candidate with Bloomberg’s resume could also win support, especially if the Democrats nominate Bernie Sanders. And even if Hillary Clinton becomes the Democratic nominee, Bloomberg might forge a winning coalition of moderates, independents, and disaffected members of both parties big enough to push him over the goal line. And money certainly won’t be a problem. The only question is: will he see an opening?

Photo by Andrew Burton/Getty Images


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