The Libertarian Party voted for a former Georgia Senate candidate, Chase Oliver, to be their party’s presidential nominee on Sunday — but the real winner of this weekend’s Libertarian convention could turn out to be President Trump.

A self-described “armed and gay” 38-year-old sales account executive, Mr. Oliver clinched the Libertarian presidential nomination in the seventh round of voting at the party’s convention at Washington, D.C., narrowly defeating a candidate endorsed by the right-leaning Mises Caucus faction of the party, Michael Rectenwald. For a party rife with factional struggles that broadly pit left versus right, Mr. Oliver’s victory dealt a blow to the right flank, which took over party leadership in 2022.

“The Mises Caucus set out on a mission to bring the Ron Paul revolution into the Libertarian Party. To shed the party of goofiness, wokeness and corruption,” a comedian and Mises Caucus de facto spokesperson, Dave Smith, posted to X. “I can’t endorse or vote for [Chase Oliver], just as he wouldn’t vote for me. He doesn’t represent me and my camp.”

Enter President Trump, who spoke at the Libertarian Party convention Saturday night to boos and calls of “liar” and “panderer” from the crowd. Seemingly unfazed by the mix of real angst and performative displeasure, Mr. Trump asked libertarians for their votes and promised in return to put a libertarian in his cabinet and to free the dark web drug site Silk Road’s founder, Ross Ulbricht, from prison.

“Only do that if you want to win,” Mr. Trump told the crowd of voting for him. “If you want to lose, don’t do that. Keep getting your 3 percent every four years.”

Vivek Ramaswamy made a similar pitch to the Libertarian Party Friday night, arguing that voting Libertarian for reasons of ideological purity — and always losing — is akin to embracing impotence. Fluent in libertarian theory and party-speak, Mr. Ramaswamy advocated for influencing policy in a liberty direction by working from the inside.

That message may be resonating — at least for some. The nomination of Mr. Oliver tipped the scales.

“Yesterday, I held up this sign calling Donald Trump supporters socialists. Tonight, the Libertarian Party nominated a gay race communist for president. With those choices, I’m standing with Donald Trump,” a Libertarian Party of New Hampshire delegate, Jeremy Kauffman, who is known for inflammatory remarks, wrote in a post to X that went viral.

Mr. Ramaswamy responded in kind. “I really respect Jeremy & the many other libertarians who have the ability to be ideological *and* pragmatic at once. It will take both to save this country,” Mr. Ramaswamy posted.

Other members of the online right like Tim Poole and Josie Glabach, “The Redheaded Libertarian,” weighed in as well, reposting pictures of Mr. Oliver wearing masks during Covid, posing with drag queens, and donning a rainbow Gadsden flag. The message: this guy is “woke,” he’s not one of us.

“He’s pro-transing kids and open borders,” Ms. Glabach posted. Libs of TikTok even got on the insult train.

“We wanted Afuera but we got this instead,” Mr. Poole posted, referencing Argentinian president Javier Milei but with a photo of Mr. Oliver in a mask.

This is not to say that every member of the Mises Caucus will vote for Mr. Trump, but the gamble he took in addressing an at-times hostile crowd and offering an olive branch in the form of promises just might pay off. Mr. Trump lost to Mr. Biden in the key swing states of Wisconsin, Georgia, and Arizona in 2020 by fewer votes than those cast for the Libertarian candidate, Jo Jorgenson. Those states cost Mr. Trump the election. He doesn’t want a repeat.

“If you vote for me, on Day One I will commute the sentence of Ross Ulbricht,” Mr. Trump said to a standing ovation. “We will get him home.”

That promise was enough to sway a handful of Libertarian convention attendees who spoke to the Sun. “He has my vote because he’s the only hope we have. Libertarianism is great but we’re not winning any elections,” an alternate delegate from New Jersey, Tatiana Moroc, told the Sun.

“I will do anything in my power to get you elected,” a prominent libertarian activist, Martha Bueno, wrote on X Monday in a post that went viral. She told the Sun before Mr. Trump’s speech that she was “a single-issue voter,” and that issue was “free Ross.”

Other Mises Caucus-aligned Libertarians told the Sun they would vote for Mr. Kennedy if they didn’t like the Libertarian Party’s nominee. Most of them mentioned Mr. Oliver by name. While Mr. Oliver got 60 percent of the vote, just over 36 percent of delegates voted “none of the above” in the final round as a protest.

Mr. Kennedy said in April he’d ruled out seeking the Libertarian presidential nomination, but he spoke at the convention Friday night, making his pitch to libertarians and attacking Mr. Trump for violating Americans’ constitutional rights during Covid. Mr. Kennedy accepted a nomination for president by video projected on the convention floor Sunday. His bid, though, was short lived. He earned only 2 percent support in the first round of voting and was eliminated from consideration.

Not all Mises Caucus-aligned Libertarians are bailing on Mr. Oliver. Antiwar activist and Libertarian Institute director, Scott Horton, told the Sun Sunday morning that he would support Mr. Oliver if he won. “Chase Oliver is really great on war and peace, so he might be considered the most opposite faction from the Mises guys, and I don’t know what his positions are on every other thing,” Mr. Horton said, “my issue far and away is war and peace.”

For anti-Mises Caucus Libertarians and those from the “old guard,” Mr. Oliver’s nomination was a hard-fought victory to be celebrated. “We saved the Libertarian Party,” the chairman of the party’s Classical Liberal Caucus, Jonathan Casey, posted to X.

Mr. Casey and others expressed concern to the Sun about the Libertarian Party’s rightward shift on issues such as gay rights, abortion, and border security. Mr. Oliver ran on a classically liberal platform, advocating for open borders and bodily autonomy on issues like abortion and transgender care. His critics, though, pounced, accusing him of advocating for vaccine mandates, though Mr. Oliver’s past statements make it clear he opposes government mandates but thinks private businesses can do as they like. These positions are hardly anathema to libertarianism.

Wearing a mask and posing with a drag queen while donning a rainbow flag, though, is kryptonite to the anti-woke right. For a party that supported gay rights and marriage when those stances were still thought to be too radical for Democrats, this is a real shift. Now, blue-haired gender-benders are mainstream, punk rock music is featured in television ads for hotel chains, and thought criminal “radicals” are embracing the “anti-woke” opposite as its own kind of religion.

The convention was not free from “goofiness” or “wokeness,” as Mr. Smith so desired. There was no stripping on stage this cycle, but a hot mic picked up a backstage conversation about race and IQ and a certain racial group’s inferior penis size while vote counting was being done on the convention floor.

The Mises Caucus-endorsed candidate, Mr. Rectenwald, made his own blunder Saturday night, consuming an edible before taking to the stage for a rebuttal press conference to Mr. Trump’s speech. This was the biggest national media platform for the Libertarian candidates, and Mr. Rectenwald sounded confused and walked off stage.

“I don’t have any judgment on anyone taking any substance so long as they can behave themselves,” Libertarian Party chairwoman, Angela McArdle, told reporters.  

The Libertarian Party may be the third-largest American political party, but it is still the redheaded stepchild. The “Become Ungovernable” convention slogan in its stylized writing looked like a Limp Bizkit album cover, the type of rebellion you’d see at a Sam Goody’s in a megamall at a suburb outside Cincinnati in the early 2000s. Now, these people are in their 30s, they run the Mises Caucus, and they like Hoppe more than Hayek, to the dismay of Cato and Reason Magazine-style libertarians.

Neither left nor right dominated the convention. Mr. Oliver won and Ms. McArdle, a member of the Mises Caucus, was re-elected to another two-year term leading the party. The 2020 Libertarian vice-presidential candidate, Spike Cohen, told the Sun this schizophrenic candidate selection is “very common of libertarians.”

Mr. Trump just needs a few thousand to defect to him, and it looks like he’ll get that.

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This article has been updated regarding the likelihood that President Trump will receive the votes of some Libertarian Party members on Election Day.