Milo Yiannopoulos, in drag as “Ivana Wall,” led a room filled with gays, conservatives, gay conservatives, Trump enthusiasts, and fellow-travelers in a chant of “Build the wall!” at a New York City bar.

The party was a prelude to the July 4th release of his book Dangerous, and the most important insight in his brief remarks to the room was probably that an influx of gays into the Republican Party is no longer primarily frightening to Republicans—rather, it is the thing that Democrats fear most.

The party location had been changed the day before the event when permission to use the original venue was revoked by the liberal restaurateur Stratis Morfogen. This was the same weekend that the large and loud fifth Transformers movie came out, and I couldn’t help thinking the man’s name sounds for all the world like that of a Decepticon.

To Milo’s publicity-generating delight, times have changed if a largely gay crowd gets thrown out of a restaurant for being too conservative rather than for being too homosexual. The left had better not use such tactics too many times if they want to avoid sending the message that conservative gatherings are where the fun, open-mindedness, tolerance, and liberty happen—just as the “anti-fascists” do themselves no favors by lobbing Molotov cocktails at the Berkeley campus when Milo tries to speak there.


A less-fringey tactical calculation that mainstream Democrat leaders must be making these days, though, is how many votes—and how much cultural cachet—they stand to lose if it ceases to be taboo for gays, or for that matter other marginalized people, to bolt the Democratic Party and vote Republican (or vote Libertarian, or not vote at all). Milo may have been in drag that night, but the evening really didn’t have the postmodern, absurdist vibe it inevitably would have back in the ‘90s, as though a gay Republican were an unlikely composite character from Northern Exposure (like a chef who is also a war veteran mistaken for Bigfoot).

The most “dangerous” element of all this for Democrats is that in time Milo will stop seeming absurd and outrageous and will just be another political option among many. Big, reliable, taken-for-granted voting blocs might bore most amateur observers, but maintaining them is a life-or-death matter to the nervous hacks tasked with maintaining majority political coalitions.

In New York City, of course, there is so much diversity that few people ever entertain fantasies of creating a majority of any kind. It’s a naturally pluralistic place in that sense, albeit hopelessly left-leaning.

The same night as Milo’s party, a friend of mine was attending an annual “All White Party” that is based not on ethnicity but on the simple idea that everyone attending should wear white. That’s about as close to homogeneity and predictability as you can get in New York. In fact, my friend is black—and likes Trump far more than I do—so it wouldn’t be surprising if he turns up at a Milo party in the future. Our whole society is soon going to be, at least, as complex and unpredictable as that, and those who run the two major parties are going to have to work to corral it all so they don’t suffer endless brutal surprises on election nights.

The night of the Milo party was also, as it happens, the 300th anniversary of the founding of the Freemasons, a reminder that the two parties may also have to factor in weird conspiracy theories like never before when tracking constituents’ beliefs. There are important beliefs that people may not even want to divulge to pollsters anymore. I almost pity the political consultants when I look to the mysterious future. Almost.

Even some of my fellow libertarians—the sort of bank-middle-manager-type libertarians who run stodgy old think-tanks—are showing signs of anxiety these days over their “natural” constituents escaping the plantation and doing the unexpected. “Shouldn’t the gay Republicans all be turning into conventional libertarians instead of some sort of new-fangled Weimar decadent-fascists?” they must think at anxiety-wracked think-tank meetings.

On the other hand, despite their libertine reputation, the libertarians might be tempted to denounce Milo for joking about accepting man/boy sex as a routine part of gay life, a revelation that got him kicked out of the annual CPAC gathering of right-wingers and the conservative establishment. Is this guy trying to make the right look evil?

But I will say this much to mainstream libertarians (to whom I bear a much greater philosophical resemblance than I do to the Milo crowd, I should note): For all the troubling fascistic notes that Milo and the alt-right sound, after seeing him in action at that party I think that his net effect on this world–and on the Republican Party–will be libertarian.

Meanwhile, what may finally bring gays and the GOP together, for good or ill, is confronting gays with a choice between radical Islam and Trump. Milo knows Trump wants to be seen as the protector of gays against terrorists, and this changes the old political calculations. The Democrats would like to be seen as the protectors of marginalized Muslims, and some cynics on the reckless far left, I suspect, would even like to make Islam the left’s cultural counterweight to the right’s Christianity. But this recruitment game may backfire for the Dems if they drive away gays, a core constituency, in the process.

I can’t help thinking that even when Trump does things like insult Mika Brzezinski’s bleeding facelift, he’s probably got a bunch of new male supporters to help compensate for any females he loses. If nothing else, soulless Dem strategists now have to crunch numbers about bizarre, petty things like that.

History takes unexpected twists and turns, even though the political class always pretends they saw it coming miles away. As a geek who respects alternate-history stories, I occasionally think about how easily environmentalism could have remained a right-wing issue if the Tories had remained staunchly agrarian, as they were in the nineteenth century. I think about how early lesbian writer Radclyffe Hall started out sympathizing with conservatives and patriarchal culture before the bonehead Tories tried to ban her writing and drove her into the arms of the socialists.

And then I think about that comedy mashup Twitter feed someone made called “Ron Paul’s Drag Race.” You never know quite what tomorrow’s coalitions—and tomorrow’s parties—will look like. I advise rooting for the people who aren’t too eager to control it all.

Todd Seavey is the author of Libertarianism for Beginners He writes for and can be found on Twitter at @ToddSeavey.