Recently, I was sent a YouTube clip that had been making the rounds online. The snippet, which was taken from 2000’s Inner Circle roast—the annual event in which assorted New York City journalists lampoon local politics—featured Rudy Giuliani, then the mayor, dressed in full drag, fending off, for laughs, what many must have viewed at the time as the surely-exaggerated-for-effect advances of the real-estate magnate Donald J. Trump. In the short exchange, the future President, grinning widely, is seen nuzzling and caressing the mayor’s bosom, as the bewigged, made-up, and fluty-voiced Giuliani calls him a “dirty boy” and slaps him. (“You can’t blame me for trying!” Trump booms.)
The clip, it turned out, was excerpted from “Giuliani Time,” a 2005 documentary about the former mayor that is still well worth a watch, particularly given Giuliani’s recent return as a lawyer on Trump’s team. What the film reminds us of—especially those of us, like me, who were not New York City residents prior to 9/11—is the underside of Giuliani’s burnished legacy as “America’s Mayor.” Giuliani, the documentary suggests, was a man who often muscled his way into being at the right place at the right time—lauded for the supposed effectiveness of his “broken windows” policy, for instance, just as crime was already on the decline nationally—and who was willing to attack, with the dual weapons of police brutality and deep welfare cuts, the often overlapping demographics of the city’s black and Hispanic minorities and its poor. Not unlike the Inner Circle clip, which might once have seemed a harmless bit of vulgarity but now chills to the bone, “Giuliani Time” reminds us of the cruelty hidden beneath that administration’s successful effort to make New York a white, upper-middle-class haven, and of the true colors of the man who has in recent weeks served, more than anything, as a punch line—the bumbling fixer to Trump’s id-like chaos monger.
