President Trump took a gamble speaking at the Libertarian Party’s convention in May, promising an ornery crowd that in exchange for their votes he would put a libertarian in his cabinet and free Ross Ulbricht, the founder of the dark web site, Silk Road, that hosted drug sales.

“Don’t waste your vote,” Trump implored the crowd to boos, taunting that they could “keep getting your 3 percent every four years” or get on the MAGA train and become “winners.”

The gamble paid off. Several high-profile Libertarians endorsed Trump. The party’s chairwoman, Angela McArdle, demurred on endorsing Trump outright, but released a video in which she said her main goal this election was to beat Joe Biden and to do so by campaigning for the Libertarian Party candidate in blue states to “pull protest votes from the left.”

Enough Libertarians voted for Trump — or at least didn’t vote for their party’s candidate — that the party didn’t play “spoiler” this election. This was a big change from 2020, when Trump narrowly lost the swing states of Wisconsin, Arizona, and Georgia by less than the votes the Libertarian candidate got.

Now, Libertarians are watching Trump’s cabinet appointments with bated breath to see whether he follows through with his promises. So far opinions are mixed. The party did celebrate Trump’s selection Thursday of Robert F. Kennedy Jr. to head the Department of Health and Human Services, calling it “a win for libertarians.”

“RFK Jr. is a registered member of the Libertarian Party, who spoke at and attended our 2024 convention, and who aligns with us on a multitude of issues,” the Libertarian Party posted to X. Mr. Kennedy told the Sun in October that he could be the libertarian Trump promised for his cabinet. “I’ve always considered myself libertarian,” he said. “Maybe me.”

Most libertarians, particularly in the Reason and Cato Institute crowds — and those who previously spoke to the Sun about this — disagree with that assessment. The Libertarian Party’s presidential nominee, Chase Oliver, says Mr. Kennedy “isn’t a libertarian. Plain and simple.”

Ms. McArdle told the Sun before the election that she had given a list of names of potential libertarian cabinet members to the Trump team. Whether Trump’s pick will be a Libertarian Party member or a self-identified libertarian or liberty Republican remains unclear.  

Some libertarians are hoping to see Congressman Thomas Massie, a liberty Republican, appointed to head the Department of Agriculture. Ms. McArdle is touting Tulsi Gabbard’s nomination to be director of national intelligence as proof “libertarians are having influence at the federal level.”

Yet other of Trump’s cabinet picks are causing consternation among libertarians.

“We need maximum pressure to keep all neocons and war hawks out of the Trump administration,” comedian and Libertarian political commentator, Dave Smith, posted to X right after the election. “They have had their time at the table and brought nothing but disaster to the world and this country.”

Donald Trump Jr. responded in a post, “Agreed 100 percent!!! I’m on it.”

Trump announced he would not include former UN ambassador Nikki Haley or former Secretary of State Pompeo in his cabinet, which pleased libertarians. Then he nominated Senator Rubio to be his Secretary of State — a pick detested by many libertarians for Mr. Rubio’s hawkish positions on the People’s Republic of China and Iran.

“Marco Rubio is a disaster,” Mr. Smith said in a post that went viral. “Might as well give Liz Cheney the State Department. Awful sign.”

“I’m not surprised nor enthused by his cabinet picks. Especially in the area of foreign policy, it looks very un-libertarian,” the Libertarian Party’s 2024 presidential nominee, Chase Oliver, tells the Sun. He calls Trump “a war criminal” and “a statist authoritarian.”

Trump was far from libertarian in his first term in office, overseeing a more than $6 trillion increase in the national debt and empowering Dr. Fauci to oversee Covid policy. Yet the president-elect does seem to be taking the liberty crowd more seriously this cycle, touting himself as the anti-war, anti-censorship, pro-cryptocurrency candidate. The newly created Department of Government Efficiency promises to slash federal spending and the administrative state.

“Wouldn’t it be great to have Ron Paul as part of the Department of Government Efficiency,” Elon Musk recently posted to X, getting applause from Libertarians who revere the former congressman and presidential candidate. Trump’s controversial cabinet picks are also giving hope to some libertarians that Trump will be more willing to buck orthodoxy in his second term and will commute Ulbricht’s sentence, critics be damned.

“Freeing Ross, compared to appointing RFK Jr. to head HHS, is the easiest thing in the world — yet another reason to believe it will happen,” a libertarian podcaster, Tom Woods, a fellow at the Mises Institute, posted to X Thursday.

Mr. Ulbricht posted this week, “Immense gratitude to everyone who voted for President Trump on my behalf.” Mr. Massie replied, “Hang in there Ross. President Trump himself told me that he would. It’s one of the reasons I endorsed him.”

A spokesperson for the Ulbricht family tells the Sun, “Neither Ross nor his family have spoken to Trump or his team since Trump won the election. They do have full confidence that he will keep his pledge to Free Ross and are deeply grateful for that.”

The Libertarian Party may be in turmoil over Ms. McArdle’s decision to put her weight and much of the party’s weight behind electing Trump, but she doesn’t seem phased. “The king maker strategy will continue,” she posted to X.