The Hill You Die On Is Still the Hill You Die On

The fall of Thomas Massie proves that ideological purity is not a substitute for political survival.

Last week, the Libertarian Party held its national convention in Grand Rapids, Michigan. Yes, there were the usual speeches about gun rights and sovereign citizenship. There were the usual hopeful declarations that America was – at last – ready for the Libertarian message. But what got the most news coverage was a bitter, fierce fight over dress codes.

Ben Weir, a libertarian candidate for county sheriff in New Hampshire, proposed that convention attendees adhere to business casual attire. No weird costumes, no see-through clothing, no using boots as headwear. And—this sparked the fiercest backlash—Weir suggested that biological males should not wear dresses or skirts.

For a movement that has long confused freedom of expression with ordered liberty, the response was predictable. “You hate freedom of speech, my dude,” one indignant official wrote. Another called Weir’s simple suggestions “anathema to libertarianism.” The measure failed after the party’s governing board deadlocked 5-5 on passage.

Defiance was the order of the day on the Grand Rapids convention floor, where someone showed up in a one-piece swimsuit while another delegate wore a thong (and not much else). In refusing to pass the Weir proposal, libertarians defended their right to dress however they pleased. They have been defending that right, and others like it, since 1971. And in all that time, they have never elected a single party member to federal office. The Libertarian candidate for president managed to get only 0.42% of the national vote in 2024. (His name was Chase Oliver. And yes, I had to look that up.)

When his proposal failed, Weir warned that “We cannot expect to get over 0.5% of the vote for our candidates if we don’t get better on our messaging to normies.” He’s right, of course. But the Libertarians aren’t listening. They’re too busy finding hills on which to die.

The Most Principled Man in the House

This same dynamic just played out earlier this month in Kentucky’s 4th Congressional District. Thomas Massie—for years, one of the most principled conservatives in the House—lost his Republican primary by nine points. In my book The Political Vise, I describe Massie as one of a very small number of “brilliant Congressmen” who “can transform the political landscape.” I meant it. During the COVID panic of 2020, Massie stood nearly alone in demanding that Congress hold an in-person debate on the $2 trillion CARES Act instead of passing it by voice vote. For his trouble, he got death threats and scorn. As I wrote afterwards, “Like Luke Skywalker in the Death Star’s trash compactor, Tom Massie got to feel just how intense and nasty the Vise’s pressure can be.”

Thomas Massie isn’t an official member of the Libertarian Party, but more than any other member of Congress, he represented small “l” libertarian principles. He was often alone, or nearly so – but for most on the right, his was a respected voice. Fiscal conservatives across the country donated to his campaigns, hopeful that others would take up his call for smaller government. For Republicans, fights over spending discipline are nothing new – and for years, Massie helped build a coalition for common sense.

In the last year, however, Tom Massie started acting less like a principled conservative and more like those iconoclastic Libertarians in Grand Rapids. In 2026, Massie made virulent opposition to Israel into his signature issue. He didn’t just vote against every spending bill that included Israeli military assistance, he condemned President Trump’s decisions on Iran. Massie then went further, publicly accusing the president of launching military strikes against the Iranian regime for the sole purpose of distracting the nation from the Epstein files.

What had begun as conduct consistent with a libertarian worldview—oppose all foreign aid, oppose all military intervention, demand transparency – turned into an angry one-man crusade. He had made a foolish calculation, assuming that his consistent principles would protect him even as he burned bridges with his own party and its president.

Massie lost his primary because he operated like a capital “L” libertarian—ideologically consistent, politically isolated, and ultimately powerless. He alienated almost everyone who would stand with him when the pressure came. When Trump and pro-Israel groups mobilized against him, he garnered endorsements from the likes of Matt Gaetz and Marjorie Taylor Greene, two former House members who had also loudly and ineffectively bucked the Republican Party and President Trump. Having considered their options, a clear majority of Republican voters in Kentucky’s 4th gave their votes to Ed Gallrein, a soft-spoken former Navy Seal who promised to support the party’s agenda.

I watched the last days of the primary unfold from Berlin, Germany in the company of a good friend who is a Massie supporter. Her husband, also a great friend, was on the ground in Kentucky working on Tom Massie’s behalf. My friends clearly did not see the Congressman’s shifts over the past year the way the district’s primary voters saw those changes. I admire and respect my friends. However, I understand that Massie lost for the same reason so many on the right lose (or never gain the power as they should): He didn’t fully embrace his actual role as a politician.

A politician’s job is to acquire political power for the purpose of advancing his philosophy. Thomas Massie had, and largely still has, a libertarian philosophy that most conservatives support. But he lost because he made what I consider tertiary and transitory issues a greater priority than the larger, generational battles for which he was long such a good warrior. In the end, he lost because he forgot the first rule of being a politician - stay electable so you can advance your agenda.

Coalitions Beat Consistency

Thomas Massie forgot that the Political Vise rewards coalition-building, not ideological purity. Yes, you can (and should!) be principled. Yes, you can have positions that others disagree with. But you must do both while maintaining relationships with allies who will defend you when the pressure intensifies. Massie had built those relationships on spending discipline. But when he turned on his party’s president – and when his rhetoric slipped dangerously close to outright anti-Semitism – he destroyed the coalition that had protected him.

The left understands this. They don’t ask whether every member of their coalition agrees on everything. Brooklyn hipsters and Chicago ward bosses probably have different views on transgender issues, for example. But the left ruthlessly maintains coalitions because they understand that political power requires unity of purpose, even amid disagreement on details. They pick their internal battles rarely and strategically, and they don’t blow up their coalitions over pet issues.

Thomas Massie can believe what he likes about why the war with Iran began. A Libertarian delegate can still wear a boot on his head on the convention floor. Both believe they hold principled positions. But principles that alienate your allies doom you to failure and defeat. Massie learned that lesson the hard way. The Libertarians, standing proudly in their swimsuits and thongs in Grand Rapids, may never learn it.