Last weekend’s Saturday Night Live opened with a gray-haired Fred Armisen as Mayor Michael Bloomberg. Donning a jacket with lapel pins and a blue tie, Armisen spoke in a dry cadence that amplified the mayor’s at once lenient but strident response to the Occupy Wall Street protests pitched at Zuccotti Park in Lower Manhattan. “Occupy Wall Street, I’m on your side,” said Armisen’s Bloomberg. “Come to New York and let your voice be heard. You’ll be treated with dignity and respect by the city and the police. With one caveat: The second and I mean the second I see a demonstrator lighting up a cigarette, we’re moving in. The batons will come out and the badge numbers will come off. And if you think I’m joking, go ahead and make my day.”

It’s easy to mock the mayor’s wary approach to the protests, but there’s more to it than one pol’s bipolar shifts or a billionaire’s shady motives. He has rigorously argued his own position, but has taken pains to coexist publicly with viewpoints he finds unpalatable; he acknowledges the demonstrator’s arguments, only to split hairs over the finer points of their analysis. Clearly, Bloomberg’s is an especially emphatic embrace of the First Amendment. But what makes his response to the protests so confounding, even troubling, is that it has revealed just how central the First Amendment is to his political vision—namely, so central that he can’t see past it.

What’s clear is that other mayors facing similar occupations from Boston to Seattle have not been nearly as compromising as Bloomberg: Most have reacted with varying degrees of alarm and force to the tent cities that have sprung up in their city centers. Last week, Boston Mayor Tom Menino authorized the forcible removal of protesters from the Rose Fitzgerald Kennedy Greenway, resulting in the arrest of 140 occupiers. “I will not tolerate civil disobedience in the city of Boston,” said Menino. In Chicago, 175 people were arrested over the weekend in Grant Park when they refused to leave following its 11 pm closing time. “I’d like to know why Bloomberg let people stay in the park peacefully and clean up their own mess, and Rahm Emanuel won’t let us do the same,” one demonstrator told the Chicago Tribune, referring to the canceled cleanup of Zuccotti Park. Seattle Mayor Mike McGinn has towed the free speech line, but revoked a permit issued for an informational tent when occupiers violated its terms by using it during hours when the park was closed. And Portland Mayor Sam Adams cleared a street that protesters blocked last week, but claimed the city was not “moving against the camps.”

Compared to that of his colleagues, Bloomberg’s response has been the most puzzling, if not paradoxical. In New York, there haven’t been any significant crackdowns since the Brooklyn Bridge occupation that led to hundreds of arrests. The Times Square demonstration yielded 42 arrests and new Zuccotti Park rules that limit tarps, sleeping bags and “lying down on the ground” so far have not been enforced. Less than two weeks ago, the mayor strolled through the narrow, crowded Zuccotti Park to announce that a cleanup had been scheduled for the coming Friday, at the behest of the private park’s owner, Brookfield Office Properties. When Working Family Parties Executive Director Dan Cantor stridently accused the mayor of initiating a “back-door attempt” to remove the protesters, the cleanup was subsequently postponed. The mayor plainly explained in his subsequent weekly radio appearance that the decision to postpone was made by Brookfield Office Properties, and that the city legally can’t clear Zuccotti unless there’s a threat to the safety of the public. On Friday, the mayor suggested again that he felt compelled to increase police enforcement at Zuccotti Park.

It’s no accident that the mayor has been disposed to this sort of discursive hedging. Bloomberg has long been fond of the First Amendment, invoking it throughout his career in interviews and speeches. “I’ve always wondered if people who block each other from expressing their opinions do so because they have so little confidence in their own,” he said in a commencement address at Tufts University in 2007. During a third term that has been marred by a series of controversies, he has been a strong advocate for the Ground Zero mosque and gay marriage. He also excluded clergy from the official event marking the 10th anniversary of 9/11. “It’s a civil ceremony,” he said at the time.

Still, the current protests have put into relief how Bloomberg’s embrace of the First Amendment can come at the expense of other, competing conceptions of justice. As eager as he is to ensure that everyone has a chance to have their say, he’s not evidently troubled by the imbalances of power and wealth that Occupy Wall Street is protesting. This is a pretty consequential blind-spot: The protesters, after all, don’t simply want to talk about inequalities, they want to correct them. Here, the mayor’s measured tones and claims of empathy are undermined by his affinity for the financial services sector. 

Bloomberg has made a strong case that the city depends on Wall Street for higher taxes that pay the salaries of teachers, firefighters, and other middle-class workers. But there’s also clearly a personal aspect to his positioning, one that he doesn’t feel compelled to apologize for. Indeed, he’s gone out of his way to defend his Upper East Side neighbors and the financial services workers he once worked alongside and employed. “Jamie Dimon is one of the greatest bankers. He’s brought more business to this city than maybe any other banker,” said Bloomberg of the JP Morgan Chase CEO at a library in the Bronx. “To go and picket him, I don’t know what that achieves.” However much the mayor prefers to present himself as a neutral umpire arbitrating the conflict, it’s daft to deny he’s actually a participant in it. Bloomberg is correct that it’s legally Brookfield Office Properties that will determine what happens to Zucotti Park, but surely it’s relevant—symbolically and practically—that the mayor’s girlfriend, Diane Taylor, happens to serve on the board of that firm.

Indeed, it’s telling that Bloomberg has had a notoriously delicate relationship with the City Hall press corps since becoming mayor. He barks at reporters when confronted with questions he doesn’t like, and his administration is cagey about providing public information and posting data online. It took more than a year to release the schedule of a close deputy who also works on the mayor’s foundation. That’s not to say that he has actively tried to censor or intimidate newspapers, but he also doesn’t hesitate to use his power to make their jobs more difficult. The press, Bloomberg’s attitude seems to suggest, has a First Amendment right to ask questions, but that doesn’t mean he has to answer them.

New York’s billionaire mayor isn’t a heartless Montgomery Burns clone. His reaction to Occupy Wall Street so far, his support of a mosque near Ground Zero, and his championing of gay marriage do reveal a hardy respect for civil rights. But he’s also not a progressive. He’s simply too pleased with the way the balance of power has shaken out in his city—not least, because he’s willed himself to the very top of it.

Jill Priluck is a writer who lives in New York.