“If you vote for me, on day one, I will commute the sentence of Ross Ulbricht,” former President Donald Trump said at the Libertarian National Convention in May. In July, Trump said at a Bitcoin conference, where many Libertarians were present, “Today I repeat my promise to commute the sentence of Ross Ulbricht.”

Many Trump supporters wondered, “Who is Ross Ulbricht?” It was the first time most of them had ever heard this name.

Ulbricht was the creator of Silk Road, a website that enabled drug-selling. He’s been imprisoned since 2013, serving two life sentences plus 40 years, virtually guaranteeing he will die in prison. Libertarians have long contended that his case is an example of government overreach and shows the need for criminal justice reform. You will find his mother, Lyn Ulbricht, at almost every Libertarian event, lobbying to free her son, with “Free Ross” signs scattered everywhere.

So when the Libertarian Party hosted the eventual Republican presidential nominee at its convention, it asked if he would free Ulbricht by commuting his sentence if reelected to the White House.

Trump said yes.

Ulbricht himself was elated. Many Libertarians were not because this was brand-new territory for their party.

Many big-l Libertarians are such because they reject the two major parties in general. For many, Trump is offensive, in particular. Those for whom being a libertarian is an integral part of their identity reflexively hate the idea of making deals with Trump. Some have strong philosophical and policy-oriented reasons, but some do whittle down to simplistic, left-tinged, “Orange Man Bad” prejudices.

Trump heard from those scorned libertarians plenty during his convention speech.

“The fact is we should not be fighting each other,” Trump told the convention on May 26.

The crowd booed loudly.

An undeterred Trump continued, “If Joe Biden gets back in, there will be no more liberty for anyone in our country. Combine with us in a partnership, we’re asking that of the Libertarians. We must work together.”

They still booed.

“Maybe you don’t want to win,” Trump said. “Keep getting your 3% every four years.”

He had a point. While the Libertarian Party runs candidates at many different local and state levels, the most attention it gets on a national scale is when its candidate runs for president. Gary Johnson, the former Republican governor of New Mexico, ran as the Libertarian presidential pick in 2012 and 2016, getting more votes than any other candidate in party history. His 3.3% of the vote in the second of those elections was its largest vote share ever.

That’s not nothing. It was a grand achievement that the party could rightly hang its hat on.

But other Libertarians are now asking, essentially, that if merely being a Libertarian is fine, what does that really get you? What’s the point?

Should being a Libertarian be about getting or achieving something?

Trump has vowed to put a libertarian in his Cabinet. He has promised libertarians he will abolish the Department of Education. Julian Assange came up during Trump’s meeting with party officials, two months before Biden made a deal not to imprison the WikiLeaks founder if he pleaded guilty to a felony charge. Other issues were also discussed.

There is a Libertarian presidential candidate running this year, Chase Oliver. But while, in the past, all of the party’s energy would be focused on his campaign, the new leadership has made the conscious decision to try to get concessions from one of the major party candidates likely to win the White House.

If Trump wins and follows through on some of his promises, the party could stand to see some causes it has championed become victories.

This type of coalition-based transactional politics is something that’s never been done before in the history of the party. After Democrat-turned-independent presidential candidate Robert F. Kennedy Jr. dropped out of the race and endorsed Trump in August — Kennedy also spoke at this year’s Libertarian National Convention — Libertarian Party Chairwoman Angela McArdle wrote on X, “Robert F. Kennedy Jr. is dropping out of his first POTUS race. [The Libertarian Party] will continue to support Chase Oliver and maintain a good relationship with Kennedy and the Trump campaign on areas of agreement.” 

“Issue coalitions are a top priority and we appreciate the broad coalitions Trump and Kennedy have been building,” she wrote. “Coalition work is the new face of politics.”

Within that 2024 coalition, Kennedy voters could matter. Kennedy himself could wind up with a significant role in a Trump administration. 

Libertarian voters might find themselves mattering, too. In a tight race between Trump and Democratic presidential nominee Kamala Harris, Republicans might need some of the 4.5 million votes cast for Johnson in 2016 or the 1.8 million votes Libertarian candidate Jo Jorgensen received in 2020.

Should Libertarians settle for another massive presidential race defeat, or is leadership right to try something different this election cycle?

This change has also come with a coup of sorts in leadership, where in 2022 the right-leaning, paleolibertarian Mises Caucus replaced the old party guard. The new leaders are inherently less likely to dismiss ideas or alliances associated with the GOP simply because it is the GOP.

McArdle told the Washington Examiner her party’s unconventional strategy of working with Trump began with people around Team Trump reaching out to Libertarians first.

“Someone adjacent to the campaign reached out to me six months ahead of time, just looking to sort of test the waters, see what my appetite might be to work together on a couple of things,” McArdle explained. “To see how libertarians in general felt about President Trump and try to get feedback. I felt like it was good-faith outreach, and I returned it in kind. No one was knocking down my door for an endorsement or anything that was really over the top.”

McArdle made clear that she didn’t come to Trump with a list of demands but was gauging where he and Libertarians might be able to work together, including getting Libertarians into his administration in high and low levels. “It was a very conversational tone,” she said. “I wanted to see where he was at.”

“The Libertarian Party, to my knowledge, has never been approached by a former president and likely presidential nominee or winner,” she explained. “I don’t think that had ever happened. I wanted to see, how do you feel about this topic, how do you feel about that topic?”

McArdle was asked if she now believes using the party’s small but substantive voter base leverage to influence major candidates should become a recurring party practice in addition to running its own presidential candidates every four years.

Without hesitation, she responded, “100%. That’s exactly what I’m doing. It’s interesting because my predecessors in the party talked about doing it. [Former Libertarian Party Chairman] Nick Sarwark’s famous quote is ‘your tears are delicious and your parties will die.’”

McArdle explained how her approach on this front is a gentler one: “The bigger context to that is that they would have to cater to us or we will spoil their elections. I take a different tone. I’m not the spoiler. I’m a fixer.”

“President Trump’s campaign and his advisers were smart enough to try to reach out and have discussions,” she added. “And anybody that does that, I’m going to treat them well, and I’m going to do everything that I can to move them in the right direction.”

“This is new for the party,” McArdle emphasized. “People are not happy about it, believe it or not. But I’m excited about it. I think it’s the correct thing to do, and other people in the party are catching on and doing it as well.”

We asked what she thought might be the breakdown between Libertarians who are happy with this new direction and those who don’t like it.

“I would say that 40% of the delegates to our national convention were very mad about it,” she replied. “Now we had 1,000 delegates. Let’s say 400 people who are really mad and let’s say they each have a friend who was, like, really mad. So maybe there’s 800-ish people who are very, very angry about it.”

“But what does that compare to the number of registered Libertarians there are in the country?” she asked. “People who are dues-paying members. People who consider themselves Libertarian. The people who complain are just a small, noisy minority.”

The Libertarian Party in 2021 had about 650,000 registered members nationally.

“I’d say that meeting with Donald Trump and talking to Republicans, to the extent that Democrats would want to talk to us, we’d do that, too,” McArdle said. “We’re leaving the bubble. That’s how we advance liberty.”

McArdle described a recent reaction within the Montana Libertarian Party of its leader, Liam McCollum, meeting with Republican Senate candidate Tim Sheehy at a Trump rally. McCollum was there to discuss Sheehy supporting the Defend the Guard Act, which would prevent states’ National Guards from being deployed overseas without a congressional declaration of war.

“People were like, ‘Oh my gosh, you can’t go to a Trump rally,’” McArdle said. “They don’t understand that you have to go outside of Libertarian events to meet non-Libertarians and advance policy.”

Thanks to McCollum, Sheehy, a retired Navy SEAL and Purple Heart recipient who served in Iraq and Afghanistan, endorsed the Defend the Guard Act. Sheehy is the front-runner in the Montana Senate race. He is facing incumbent Sen. Jon Tester (D-MT).

The Libertarian Party chairwoman described her frustration with fellow party members who believe outreach to the major parties is somehow bad. “What do you think happens when you get elected?” she asked. “That you just sit in an office apart from everyone else and you don’t interact with the other people who were also elected to office?”

“It’s a very juvenile outlook on politics that I think some of the party cultist types, as they call them, have,” McArdle added. “We’re breaking out of that mold.”

While many Libertarians might not like this new strategy, many others are eager to see if it bears fruit, giving Libertarians policy victories they have rarely achieved through their party at the ballot box.

“Right now, paradoxically, we’re the least likely to get elected, but we are the most powerful voting bloc in the country,” McArdle added.

If the margin between Trump and Harris is as razor-thin as the polls forecast, it might not take much for Libertarians to shape the outcome.

Jack Hunter (@jackhunter74) is a contributor to the Washington Examiner’s Beltway Confidential blog. He is the former political editor of Rare.us and co-authored the 2011 book The Tea Party Goes to Washington with Sen. Rand Paul (R-KY).