New York City politics is littered with wannabe-next-mayors who never made the final cut, but Anthony Weiner may be the first one ever to wind up in federal prison. “Hit ‘send’ in haste, do hard time at leisure” is a life lesson Weiner learned one teenager too late, and now he’s to be fitted for a Bureau of Prisons jumpsuit on November 6.

If there is one lesson to be taken from Weiner’s salacious antics and his subsequent downfall, it’s that Gotham’s forgiving-to-a-fault electorate will put up with some perversity in its politics—but even New Yorkers have limits. Forced from Congress by a sexting scandal in 2011, Weiner was a strengthening front-runner in the 2013 Democratic mayoral primary when he was caught in a second sexting incident. That was the end of his career—but not, sadly for him, his compulsive cyber-perversions.

The crimes for which federal judge Denise Cote ordered Weiner jailed for 21 months occurred just last year, and involved a 15-year-old North Carolina girl. The details are repulsive, but they fit the patterns of Weiner’s life: he’s a man with demons, but no self-control—a toxic combination. Not that he lacked charm, when it suited his purposes. He’d flash beguiling smiles in public—especially when the news cameras were on—while saving a singular, arrogant smirk for those forced to deal with him at close quarters, rarely a pleasant experience.

Weiner’s rise to prominence in New York politics was unexceptional, but swift; early on, he established himself as mini-me to now U.S. Senate Minority Leader Charles D. Schumer—following the more senior Democrat first into the state assembly and then to Congress, as Schumer’s career progressed. The physical similarities between the two were remarkable (even if Weiner’s Schumeresque mannerisms often seemed rehearsed); they loyally served their Brooklyn-Queens constituencies, which reciprocated by re-electing them. Neither man bothered to mask his ambition.

But while Schumer was focused on Washington, Weiner made no secret of his ultimate goal of running City Hall. He might have made it but for his arrogance and lack of self-discipline. Of the latter, there was plenty of warning: Weiner’s House-floor tirades were epic and, indeed, his spittle-flecked savaging of Representative Peter King, a Republican colleague from Long Island, over a 9/11 relief bill drew national attention. That tantrum came shortly before the wheels came off for Weiner, and it never received the attention it deserved—a pity, because it presaged what sort of a mayoralty the now-prison-bound pol would have run. 

Histrionics are no vice in contemporary American politics, just as moderation is rarely a successful strategy, and in that respect, Weiner would have fit right in. At a minimum, Weiner would have stretched thin Governor Andrew Cuomo’s own high-maintenance ego—not necessarily a bad thing, as Mayor Bill de Blasio’s milquetoast approach to Albany isn’t paying dividends—and the cardboard cutouts on the city council would have been no match for him.

But at what price? That’s objectively unknowable, but given Weiner’s demonstrated inability to control his, um, cellphone, it seems reasonable to assume that when his moment arrived, it would be spectacularly unpredictable. Weiner’s story is nothing if not multifaceted. The FBI probe that produced his conviction led first to the laptop he shared with his estranged wife, Hillary Clinton aide Huma Abedin, which, in turn, led to a pile of Clinton emails—which, some believe, led straight to the presidency of Donald Trump.

The mere possibility that the Man Who Would Be Mayor caused or helped cause Donald Trump’s presidency is enough to guarantee that New York will never forgive Anthony Weiner—the golden boy brought low by his compulsions. It’s not exactly Shakespearean tragedy, but it’s close enough for our depleted times.

Photo by Drew Angerer/Getty Images


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