The Republican Who Outsmarted Trump

Photographs by Caroline Gutman Representative Thomas Massie, the renegade Kentucky Republican who fiercely guards his political independence, doesn’t love being on President Trump’s bad side. He would prefer not to have the president’s allies spend millions to defeat him in a primary. In fact, if Massie had his way, he’d be working for Trump right now. In his telling, in the weeks after the 2024 presidential election, the two men talked about Massie, a farmer who champions raw milk, becoming Trump’s agriculture secretary. Massie had formally endorsed Trump late in the campaign, offering to help him win over libertarians who might be tempted to stay home or vote third party in key battlegrounds. Trump had been appreciative, and the two had chatted by phone to hash out the timing of the endorsement announcement. “Just tweet it. I’ll retweet you,” Trump had told him. The rollout went smoothly, but Massie’s endorsement didn’t get him the job in Trump’s Cabinet. He was recounting this to me in, of all places, a bridal suite inside a converted barn in his northern-Kentucky district. Massie had just delivered remarks to a friendly crowd in the wedding hall downstairs, part of an acrimonious campaign that, if Trump gets his way, will be Massie’s last. The president’s allies are spending big to defeat Massie in a May 19 primary and prop up Ed Gallrein, a Navy SEAL and a political novice whom Trump personally recruited as a challenger. Massie first won election to the House during the pre-Trump Tea Party era and has handily prevailed in competitive primaries before. But he is also aware of Trump’s unique hold on the GOP: When the president decides he wants a Republican out of Congress, he usually gets his wish. Polls have given Massie a lead over Gallrein, who is not well known in the district, but his advantage is far smaller than in his previous reelection bids. Trump attacks Massie anywhere and everywhere, whether it’s on Truth Social (“A totally ineffective LOSER”), at an event in Massie’s district (“He’s the worst!”), or at the National Prayer Breakfast (“Moron”). He’s even impugned Massie’s new wife, accusing her of being “Radical Left” (Massie says that she voted thrice for Trump) and suggesting that Massie remarried too quickly after the death of his first wife. Massie, by contrast, often talks about Trump less like he’s a sworn enemy and more like he’s a jilted ex who’s still a bit obsessed with him. “I don’t feel like I’m fighting with him,” Massie said. What Trump sees as betrayal—Massie’s drive to release the Epstein files and his opposition to core parts of the president’s agenda—Massie merely described as an occasional “policy disagreement.” As he campaigns in a district that backed the president in 2024 by nearly 36 points, he’s urging voters to keep some perspective on his breaks with Trump. He insists that, far from being a Never Trumper, he’s a Mostly Trumper. In one ad, Massie points out their previous endorsements of each other and says, “I agree with President Trump nearly all of the time.” Another spot highlights his support for the Save America Act, an election bill and Trump’s top legislative priority. “This is going to be a referendum on whether it’s okay to vote with your party 90 percent of the time or whether you have to do it 100 percent,” Massie told members of the Grant County Republican Party inside the converted barn. [Read: A serious Senate debate about an unserious bill] In Washington, Massie is known for his ideological consistency during his seven terms in the House—Trump is just one of several GOP leaders he’s crossed in the name of principle—and for relishing the attention that his squabbles with the president have attracted. But Massie takes pride in his willingness to defy Trump when so many in his party will not. He predicts that if he can survive Trump’s bid to defeat him, his victory will embolden more Republicans in Congress to stand up to the president. “There would be six to a dozen congressmen who are more liable to vote with their constituents instead of the party line,” Massie told me, saying that he had spoken with some of them directly but declining to name them. Needless to say, this does not sound like a Republican who would have lasted long in Trump’s Cabinet. Massie admitted to some ambivalence about the prospect. He said that he used to joke about placing an important condition on an administration job. “I need a small jet capable of reaching Argentina on the tarmac, with enough fuel in it to get out of the country, if I work in his Cabinet,” as Massie told it, “because everybody’s going to get impeached or fired or go to jail.” Massie came to Congress as a spending hawk, and more than a decade later, that remains his signature issue and the source of many of his disagreements with GOP leaders. “They say I vote ‘no’ a lot. But I really vote ‘Don’t spend,’” Massie told the gathering of approximately 100 Republicans in Grant County, which is about 45 minutes south of Cincinnati. He opposes foreign aid and voted against Trump’s One Big Beautiful Bill Act last year because of projections that its tax cuts would explode already ballooning deficits. Massie built a clip-on debt clock that he wears on his lapel—one of a few dozen inventions for which the former robotics engineer has or is seeking a patent. “You just spent like $100 million talking to me,” he noted to me, a taxpayer, nearly a half hour into our interview. Barely 40 when he was first elected to the House, Massie was pudgy and rosy-cheeked, with the kind of youthful appearance that often gets newly elected lawmakers confused for staffers inside the Capitol. “He looked like a teenager,” recalls Phil Moffett, a former GOP candidate for Kentucky governor who encouraged Massie to run and then chaired his campaign. Massie, 55, is a grandfather now. He appears slimmer and more weathered, with a short gray beard—a physical transformation that he jokes about in one of his ads. Massie speaks with less of an obvious filter than most congressional Republicans. His impersonation of Trump, which he deploys frequently, more closely resembles the cartoonish, lip-puckering Alec Baldwin bit on Saturday Night Live during the president’s first term than it does James Austin Johnson’s more recent interpretation. Within his district, Massie loves to tell voters how cheap he is. The first story he shared during his speech in Grant County was an elaborate yarn about the time he’d spent as judge-executive—essentially the mayor—of Lewis County in the years before he ran for Congress. The water heater at the county jail had broken down, leading the jailer to complain to Massie because the inmates were refusing to shower and “were getting kind of rank,” Massie said. Massie didn’t want to bill taxpayers the $12,000 quoted as the cost of a replacement, so he found a water heater on eBay for $5,500. To save more money, he installed it himself and then invited the inmates to strip the old water heater “for everything it’s worth” so that the county could sell the parts. “I know you were in here for stealing copper and whatever,” Massie said he told them, “so you probably know everything that's worth anything on that hot-water heater.” For good measure, they peeled the green inspection sticker off the old heater and slapped it on the new one. “They said, ‘Judge, you could go to jail for this,’” Massie said. To which he replied, “I’ll have a hot shower, though, won’t I?” The prison tale reminds voters about the fiscally prudent conservative they first sent to Washington in 2012. Kentucky’s fourth district covers a chunk of the triangle between Cincinnati, Louisville, and Lexington in the northwest corner of the state and then stretches east through several rural counties close to the West Virginia border. Massie rode the tail end of the Tea Party wave, dominating a seven-way primary and a special election to replace a retiring Republican who was more closely aligned with the part…