Donald Trump’s least favorite House Republican, Representative Thomas Massie of Kentucky, likes to do an exaggerated impression of the president. As he recounted a long-ago phone call from Trump before a crowd of supporters in his district, Massie dropped the register of his voice to an octave resembling Yogi Bear’s. “It started out with: I’m more libertarian than you are,” Massie said. “And it ended with: Well, you’re going to get a primary if you vote for this.”
The eruption that followed created a scene that you’re unlikely to see anywhere else in America these days: a roomful of Republicans laughing at Trump’s expense.
The 54-year-old has been frustrating Trump since the beginning of the president’s first term. The two are now fighting over the extent of Trump’s war powers—Massie called the air strikes on Iran unconstitutional—and the president’s “big, beautiful bill,” which the seventh-term lawmaker opposed, one of just two House Republicans to do so.
Massie is frequently a lone critic of the president in the 220-member House GOP caucus. But he’s not such a solitary voice in the Kentucky delegation. The Bluegrass State backed Trump by 30.5 percentage points last year—one of his largest margins in the country. Nationwide, Republicans are more united around Trump than they’ve ever been. Yet Kentucky has become a rare hotbed of GOP resistance to the president’s agenda.
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Senator Rand Paul of Kentucky, an early Trump presidential rival in 2016, is an ideological ally of Massie’s; he’s criticized the president’s tariffs, his expansion of executive authority, and the deficit-busting legislation that contains the bulk of Trump’s economic agenda. Then there’s the state’s senior senator, Mitch McConnell. Liberated from his commitments as Republican leader, the soon-to-retire McConnell has denounced Trump’s Ukraine policy and his tariffs. He voted against more of the president’s Cabinet nominees—Pete Hegseth, the defense secretary; Robert Kennedy Jr., the health secretary; and Tulsi Gabbard, the director of national intelligence—than any other GOP senator.
McConnell, Paul, and Massie occasionally oppose Trump from different sides. But together they form a powerful bloc among the seven Republicans in Kentucky’s eight-man congressional delegation, and their stands against the president are angering many of Trump’s diehard supporters in the state, who feel oddly unrepresented by the lawmakers they’ve sent to Washington. “We voted for Trump to straighten some things out,” Devon Cain, a 77-year-old retiree, told me outside a farm-supply store in Winchester, a small town outside of Lexington. “Why a Republican would want to buck him, I don’t know.” Mark Wallingford, a physician in rural Mason County, is even more livid. “I will not vote for Thomas Massie. And if he is unopposed, I just wouldn’t vote,” he told me after a local GOP meeting.
The clashes between Trump and the Kentucky trio are a sensitive topic among state GOP officials, many of whom are hesitant to take sides against either the popular president or their influential local leaders. “I’m MAGA all the way, and I’m Massie all the way,” Ken Moellman Sr., a retiree and one of Massie’s constituents in northern Kentucky, told me. He compared the Trump-Massie relationship to a marriage. “Sometimes you disagree, but when you disagree, that doesn’t mean you get divorced.”
The twice-divorced president seems to be pining for a breakup, however. He has repeatedly called for Massie’s defeat in a primary—“GET THIS ‘BUM’ OUT OF OFFICE, ASAP!!!” Trump posted on Monday—and two of his top allies have formed a Kentucky political action committee to recruit a GOP challenger in Massie’s district. The group began running a 30-second ad last week urging voters to “fire Thomas Massie.” Although Massie has aggressively raised money off the president’s attacks, he professes to not care about the threat to his seat. Trump, Massie likes to boast, earned fewer votes in Kentucky’s Fourth Congressional District than he did. “I’m not worried about losing,” he told me last month in the Capitol.
To outsiders, Kentucky’s politics can be hard to grasp. In some respects, the state is no different than any other Republican stronghold. Outside of the urban centers of Louisville and Lexington, Kentucky is largely rural and conservative. The state has not backed a Democrat for president or for the U.S. Senate since the 1990s. All but one of Kentucky’s six House members are Republican, as are the majorities in both chambers of its legislature.
But even as the state has gone decisively for Trump the past three elections, it has twice elected a Democratic governor, Andy Beshear. And the pair of Republicans that voters have sent to the Senate, McConnell and Paul, are as different from one another as any two senators from the same party in the country. McConnell is the institutionalist: a Reaganite and a Kentucky power broker who is now one of the last members of the GOP’s old guard still serving in Congress. Paul arrived in Washington as part of the Tea Party wave of 2010, having upset a McConnell-backed front-runner in the primary by campaigning as a spending hawk. Massie won election to the House two years later on the Tea Party banner. “We’ve always been a bit all over the place in the candidates that we support,” Rick VanMeter, a strategist from Kentucky who has worked for several Republicans in the state, told me.
Although McConnell and Paul vote with Trump more often than they cross him, the president lacks a loyalist in the state’s most powerful offices. That will probably change after next year’s election to fill McConnell’s seat, which Republicans will be heavily favored to win. The two leading candidates, Representative Andy Barr and Kentucky’s former attorney general Daniel Cameron, are each stressing their support for Trump’s agenda. Another contender, Nate Morris—who has ties to Vice President J. D. Vance and Donald Trump Jr.—joined the race this week.
None of them is likely to highlight their connection to McConnell, whose popularity among Kentucky Republicans has plummeted in the years since he steered Trump’s tax cuts and the president’s three Supreme Court nominees through the Senate. (In fact, McConnell has been America’s least popular senator for more than four years, according to one metric.) McConnell blamed Trump for the Capitol riot on January 6 (although he voted to acquit him in the Senate’s impeachment trial), and he endorsed Trump only reluctantly last year. Multiple falls and freezing spells have slowed the 83-year-old, contributing to his decision not to seek an eighth Senate term in 2026. As I traveled around Kentucky last week, a few Republicans hailed McConnell’s past leadership and the billions in funding that he’s secured for the state. But hardly anyone I spoke with was sad to see him go. “I can’t stand him. He’s a traitor,” Don Reilly, a Trump backer and former president of the Boone County Business Association in northern Kentucky, told me.
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The conflict among Republicans has put Kentucky Democrats in the awkward position of rooting for Paul, Massie, and McConnell to hold the line against Trump, with the hope that their opposition could force him to retreat on tariffs or sink the president’s megabill. Last week I found a group of Democrats demonstrating outside of McConnell’s office, urging him to reject the GOP legislation that would slash Medicaid while extending Trump’s first-term tax cuts and boosting spending on immigration enforcement and the Pentagon. They were unimpressed by McConnell’s more recent criticism of Trump. “He gets credit for that, but it’s too little, too late,” Leah Netherland, a 69-year-old retiree, told me. “He is in large part responsible for Trump.”
Beshear, whose success in a deep-red state has attracted national notice, seems to be watching the GOP infighting with some bemusement. “If Senator Paul, Senator McConnell, and I all say that tariffs are a bad idea, it’s because they’re a really bad idea,” the governor told me after a Juneteenth event in Lexington. Yet Beshear can only cheer them on so much. None of the Republicans battling Trump are centrists; Paul and Massie are opposing the president’s bill because it doesn’t cut spending deeply enough. “The bill needs to die, but not for the reasons they’re talking about,” Beshear said.
The louder voices of discontent in Kentucky, however, are coming from Trump’s base, which is heeding the president’s call to ramp up pressure on his Republican critics. With McConnell retiring and Paul not up for reelection until 2028, the immediate target is Massie. Trump’s backers in Washington and Kentucky are casting about for a serious challenger in Massie’s district, and a few state legislators are considering the race, Republicans in the state told me. (One conservative, Niki Lee Ethington, a nurse and former parole officer, has launched a campaign, but she is not well known throughout the district.) Massie’s base in northern Kentucky has a large libertarian contingent, and since his first reelection in 2014, he’s never won fewer than 75 percent of votes in a primary.
But a well-funded, Trump-backed campaign, should one emerge, would be something else entirely. In addition to motivating the president’s frustrated base, a challenger could activate local Republicans who believe Massie’s refusal to fight for the district’s share of federal spending has hurt its bid for needed infrastructure projects. “They’re kind of over Massie’s schtick,” VanMeter, the GOP strategist, told me.
Gallatin County, which sits along the Ohio River about an hour’s drive south of Cincinnati, is the second-smallest of Kentucky’s 120 counties. It’s one of 21 counties in Massie’s congressional district, which stretches nearly 200 miles from the outskirts of Louisville to the state’s eastern border. Last week, the quarterly meeting of Gallatin’s Republican Party drew just eight attendees, who sat around folding tables at the public library in Warsaw, the county seat. The main order of business was a vote on whether to spend some of the roughly $1,800 that the committee had in its campaign account—a number nearly equivalent to Warsaw’s population—on new signage for the party to display at festivals, county fairs, and other events.
The bickering between Trump and Kentucky’s GOP rebels did not come up, and perhaps that was for the best. Like many party organizations in the district, Gallatin’s Republicans are divided over the Trump-Massie feud. The committee’s vice chair, Wayne Rassman, told me he had grown frustrated with Massie’s opposition to the president. “He’s not listening to the people in his district,” Rassman told me. “I don’t know what made him go off the deep end.” The party treasurer, Donna Terry, said that she used to be for Massie but no longer is. “I’m a little fed up,” she told me. Both of them said they would probably back a primary challenger next year.
The chair of Gallatin’s GOP is Jim Kinman, a 51-year-old delivery specialist. He accepted the post reluctantly, explaining to me that the state party had told the county committee that it would be disbanded if it didn’t elect a slate of officers. When I caught up with Kinman after the meeting, he lowered his voice before wading into the Trump-Massie fracas. He said that he had never gotten into the “cultish” dynamic surrounding Trump, whom he did not support in 2016. “Generally, he’s done a good job,” Kinman said of the president. But, he added, “when the rubber meets the road, I’m going to be with Thomas.”
Kinman told me that his loyalty to Massie has caused consternation among his fellow Republicans in the area, but he wasn’t budging. “Thomas legitimately is the only person I trust more than myself,” Kinman said. Whereas many Kentucky Republicans want their representatives to back Trump unconditionally, Kinman said he admired Massie’s adherence to his longtime principles. He compared him favorably to Paul, who is often aligned with Massie but has been a bit more open to compromise during the Trump era. (Kinman had nothing nice to say about McConnell, referring to him both as “a snake” and “the turtle.”) “We got plenty of people that are for rent,” Kinman said of politicians who too easily trade away their values. “I’m glad that Thomas is not.”
Massie was about to go bowling last weekend when Trump bombed Iran. With the House on recess, he was back in his district for an event with the Northern Kentucky Young Republicans, a group filled with his acolytes. The gathering was a relaxed affair—Massie nursed a Michelob Ultra and wore an untucked turquoise polo shirt—and represented a small show of force for his standing in the area. The organization has hosted other prominent Kentucky Republicans, including each of the major potential GOP contenders to replace McConnell in the Senate. But its president, T. J. Roberts, told me that Massie’s event was the best attended.
At 27, Roberts is the second-youngest state legislator in Kentucky history and one of several conservatives known as “Massie’s Nasties” for their loyalty to the seven-term representative—and for their occasional hardball campaign tactics. Like many at the bowling alley on Saturday night, Roberts said that he admires Massie and Trump with equal fervor. He told me that he didn’t take the president’s demand for a primary challenge seriously. “President Trump is using this as a pressure technique against other members who may sway,” Roberts told me. “It’s a smart move. If I were in his shoes, I’d do the same thing.” As for Massie, Roberts said: “He’s inoculated from primaries.”
Yet without impugning Trump, Roberts made sure to remind the crowd of around 80 people of Massie’s MAGA credentials. “There is no one who represents MAGA in Congress better than Thomas Massie,” Roberts said. “He was MAGA before MAGA was a thing.”
Massie began his speech by reminding the crowd of his overall support for Trump, but he tackled their disagreements head on, starting with the impending confrontation with Iran. Touting the resolution that he had introduced to block the president from ordering a unilateral military attack, Massie said, “I have his respect, and he has mine, but he cannot engage us in a war without a vote of Congress.” The crowd applauded his stance. But unbeknownst to Massie, his argument was all but moot: Soon after he left the stage, Trump announced that U.S. warplanes had already struck Iran’s nuclear sites.
Like Trump, Massie is a storyteller who revels in sharing behind-the-scenes anecdotes that many politicians prefer either to keep private or to divulge without their names attached. Sass is a core part of his image, both in person and on social media, where he frequently uses the tagline #sassywithmassie. (Earlier this week when Vance wondered whether other vice presidents experienced “as much excitement” as he has, Massie responded on X: “Ask Mike Pence about his last month,” referring to January 6.)
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During his speech, Massie argued that Trump respected him “because he knows I’m not a yes man” while also slyly mocking the president in ways that few Republicans dare to do in public. Massie described a House Republican conference meeting last month during which Trump droned on about him for so long that he had assumed the president was talking about someone else. At one point, Trump compared Massie with Paul. “They’re both from Kentucky, you can never get them to vote for anything, and they basically have the same hair,” Trump explained, according to Massie. “Actually,” the president quickly added, “I like Massie’s hair better.” As the crowd at the bowling alley laughed, Massie quipped, “Take the wins where you can get them!”
Despite Massie’s outward confidence about the prospect of a Trump-backed primary challenge, he has made some small moves that suggest a desire to declare a truce. He agreed to withdraw his war-powers resolution after Trump announced a cease-fire between Israel and Iran, at least temporarily abandoning the Democrats who planned to push it forward anyway. And although Massie voted against Trump’s megabill when it passed the House last month, he insisted that he was open to supporting its final passage if the Senate makes changes to his liking. “I’m a gettable vote!” he told me after his speech. (He explained his thinking this way to his supporters: “I’ll vote for a crap sandwich. I just want a pickle and two slices of bread.”)
I posed to Massie the question that had brought me to Kentucky in the first place: Why does a state that voted so strongly for Trump have such a disproportionate share of the president’s GOP critics in high office? He replied by invoking Kentucky’s divided status in the Civil War. “We were a border state,” Massie said. “We are independent in Kentucky, and I don’t think you can take our vote for granted, whether it’s representatives or constituents.” The coming months will test if that long-ago legacy still applies. Kentucky has clearly picked a side in the modern political wars, and its Republican voters must decide whether to force their remaining elected holdouts to join them.
*Lead image credit: Illustration by Allison Zaucha / The Atlantic. Sources: Tom Williams / CQ-Roll Call, Inc / Getty; Kevin Carter / Getty; Chris Kleponis / CNP / Bloomberg / Getty; Sepia Times / Getty
