As Bloomberg groped toward finding a quiet resolution downtown, the Post was turning up the pressure, with front-page stories demonizing the demonstrators. Deputy Mayor Howard Wolfson tried to discuss a nonviolent endgame to Occupy Wall Street, meeting with a group of its representatives on October 31. The conversation never got past the city’s refusal to allow portable toilets, and Wolfson says he grew frustrated with the protesters’ leaderlessness. A little more than a week later, Wolfson, a history buff, mentioned to me the 1874 occupation of Tompkins Square Park after a national financial crisis. “We tend to think the stuff we’re living through has never happened before,” Wolfson said. Later that night a city medical worker was injured responding to a call in Zuccotti Park. Five days later, claiming that the encampment had become a menace to public health and safety, Bloomberg sent in the troops. It was a tactical triumph, and a vast improvement on the recent violence in Oakland and Seattle—not to mention on Tompkins Square Park in 1874, when police on horseback bludgeoned protesters. But launching a sneak attack, and keeping it out of sight of reporters to “protect” them, forfeited the high road Bloomberg had tried to walk and stoked the battles between cops and OWS that erupted two days later.
Thursday, as hundreds of protesters skirmished with cops downtown, the mayor finally showed that he might have gotten the larger message. “The public is getting scared. They don’t know what to do, and they’re going to strike out,” he said. “They just know the system isn’t working, and they don’t want to wait around for another bullshit promise.” Less heartening: that Bloomberg chose to share this epiphany in a crowd that included fellow plutocrats like Rupert Murdoch, making it sound as if he was suggesting they’d all be wise to double up on bodyguards. The next morning he was back on the air with Gambling, edging toward the downright conciliatory. “They don’t know how to coalesce and get the message out,” the mayor said of OWS, “but that doesn’t mean that what they’re complaining about isn’t real.”
Back when Bloomberg was running for his second and supposedly final term, I tried to get him to reflect on how money had changed his life and whether he thought he deserved the billions he’d accumulated. “I’m not smarter or better than anybody else,” he said. “I just happen to be in a business where the rewards were more financial.” Despite the houses in Vail, London, Bermuda, and elsewhere, Bloomberg insisted that he still sees himself as a kid from small-town Massachusetts, the ordinary son of a middle-class bookkeeper. It would be nice to believe that’s even partly true. But one consequence of electing a mayor as wealthy as Michael Bloomberg is that he would have difficulty engaging with the mind-sets of people less well-off. And one of the victories of Occupy Wall Street is that he’s had to work at it.