A few steps from the Boone County Courthouse in the northern Kentucky town of Burlington, Representative Thomas Massie was about to hold a public event a little over a week before voters would decide whether to keep him in office.
A boy walked up and offered him a piece of Pez candy.
“You know, President Trump hands out endorsements like you hand out candy,” Mr. Massie told the boy with a wry grin as he accepted the gift. “Just not to me.”
Mr. Massie was referring to Mr. Trump’s support for his opponent Ed Gallrein, as payback for his frequent apostasies. Mr. Massie had voted against the president’s tax legislation, calling it not frugal enough. He had voted repeatedly against the war in Iran and condemned aid to Israel as a misuse of taxpayer money. Most conspicuously, Mr. Massie had helped lead the charge to compel the release of the Epstein files despite the president’s resistance.
Mr. Trump has vowed to replace the man he has variously termed a “moron,” “loser” and “total disaster” with someone more loyal. In October, he settled on Mr. Gallrein, a dairy farmer and retired Navy SEAL captain.
The result is that Mr. Massie, who has never faced serious opposition since first winning office in 2012, now finds himself in a tough fight. He says his campaign’s internal polling shows the race deadlocked, but some recent public surveys have shown Mr. Gallrein ahead.
The Republican contest for the Fourth Congressional District is likely to be remembered as one of the costliest, ugliest and most consequential primaries this year. It also serves as the latest indicator of Mr. Trump’s political clout, which showed continued durability over the weekend when Senator Bill Cassidy of Louisiana, whom the president had targeted for defeat, lost his primary and a Trump-backed challenger was the top vote-getter.
A victory by Mr. Gallrein would be seen by other Republicans as the latest evidence that the president’s hold over the party remains absolute, even in the face of his sagging approval ratings. Mr. Massie hopes voters will opt to keep him and prove the opposite.
“You can send him a message,” Mr. Massie told his audience inside the courthouse last week, referring to the president. “He needs to work with me because I ain’t going anywhere.”
‘He Can’t Get Anything Done’
The race is also a referendum on Mr. Massie.
Despite being a seven-term incumbent, the Kentucky maverick is more comfortable in the role of outsider.
An eccentric who lives off the grid on a small cattle ranch and guzzles raw milk, the 55-year-old West Virginia native holds an engineering degree from the Massachusetts Institute of Technology as well as several patents.
Trey Grayson, a Republican and former secretary of state in Kentucky who lives in the district and is neutral in the race, recalled once seeing Mr. Massie tell a classroom of teenage students that he had disliked cleaning his room when he was their age and therefore invented a robot to do the job for him.
Like his political mentors Ron and Rand Paul — the former a retired Texas congressman, the latter a U.S. senator representing Kentucky — Mr. Massie has libertarian leanings.
In Congress, he quickly developed a reputation for opposing nearly every federal spending measure that came up for a vote. In an interview, Mr. Grayson recalled the senior Kentucky senator, Mitch McConnell, once asking Mr. Massie: “Thomas, have you voted ‘yes’ to anything since I last saw you?”
Mr. Massie said his independent streak was very much in keeping with the anti-establishment predilections of Mr. Trump’s base.
“I’m not a go-along-to-get-along congressman,” he said in an interview. “And that has endeared me to a lot of the constituents who are part of this coalition that put us in the White House.”
But it has also tested the patience of fellow Republicans.
“I backed him for a number of races,” said Steve Frank, a former city commissioner in Covington who now supports Mr. Gallrein. “But the heart of the problem with Massie is that he has no throw-weight. He can’t get anything done.”
Mr. Grayson concurred with Mr. Frank’s assessment.
“He has allies, but he hasn’t turned them into an effective coalition,” he said.
His defenders argue that Mr. Massie should not be faulted for being the rare officeholder in Washington to refuse to compromise.
“Massie’s principled,” said Patty Brueggemann, who attended the congressman’s event at the Boone County Courthouse with her teenage son. “Everybody knows where he stands.”
As evidence that Mr. Massie could in fact get things done, Ms. Brueggemann said, “He got the Epstein files released. For me, that’s big.”
But Mr. Massie did so alongside Democrats, and in defiance of Mr. Trump’s wishes, which did not sit well with every constituent.
One such voter, Elizabeth Smith, a graphic designer and former candidate for Boone County commissioner, said in an interview that she had voted for Mr. Massie in the past but was now “on the fence.”
“I’ve just felt like as of late he’s been grandstanding,” she said. “But maybe — I’m kind of having an epiphany right here — maybe it takes a strong personality to work with President Trump.”
Ms. Smith said that she admired Mr. Massie’s willingness to take nearly two hours’ worth of questions from constituents that evening, while his opponent, Mr. Gallrein seemed to shy away from such engagement
“He just doesn’t impress me at all,” she said.
‘For Thomas or Against Thomas’
In March, Mr. Trump, a former reality TV star, bestowed the ultimate compliment on his handpicked opponent to challenge Mr. Massie, saying on social media that Mr. Gallrein was out of “central casting.”
He is a fifth-generation farmer, a recipient of four Bronze Stars, at least one from Afghanistan, for valor in combat and a churchgoing conservative with a ramrod bearing. The 68-year-old war veteran has been known to bring along his military regalia to campaign events and to litter his monologues with references to corn-growing and hay-baling.
Mr. Gallrein is also quick to say, “I’m not a politician,” though this is his second attempt at elective office after being defeated in a State Senate primary two years ago.
His most salient credential is Mr. Trump’s seal of approval. In speeches, the candidate often points out that 85 percent of the district voted for Mr. Trump in the 2024 primary, asserting that residents deserved a congressman who would be in lock-step with the president.
Mr. Massie, he said, “has a problem for every solution.”
Mr. Massie has maintained, in turn, that his opponent would be little more than a yes-man to the president. When a New York Times reporter put this claim to Mr. Gallrein, he bridled.
“I guess I should have gotten five Bronze Stars to demonstrate my personal courage and independence to act on my own,” he said, adding: “I am no rubber stamp. Will never happen.”
However, when asked in a brief interview what House committees he would like to serve on, Mr. Gallrein said he would defer to the president and his allies, including Speaker Mike Johnson and Vice President JD Vance.
“I’m gonna go to Speaker Johnson and the president and JD,” he said. “I’m gonna say, ‘Where do you need me, coach?’”
Mr. Gallrein had not been the president’s first choice to run against Mr. Massie. That distinction went to the man who defeated Mr. Gallrein in his 2024 State Senate race, Aaron Reed, who is also a retired Navy SEAL as well as a gun store owner.
In an interview, Mr. Reed said he had visited the White House last summer to discuss challenging Mr. Massie in the Republican primary but had ultimately decided against it and was staying neutral out of respect for Mr. Trump. Still, Mr. Reed’s assessment of Mr. Gallrein was less than glowing.
“He has the personality of a rock,” he said. “I don’t think anybody’s going to vote for Ed Gallrein. They’ll either vote for Thomas or against Thomas.”
The minimalist nature of Mr. Gallrein’s campaign seems to be an implicit acknowledgment of his limitations in retail politics. His encounters with the district’s voters have been closed to the media. He has skipped all eight scheduled debates with Mr. Massie. He planned to appear on Monday at an event in Hebron, Ky., alongside Defense Secretary Pete Hegseth.
But what the Gallrein campaign has lacked in large rallies and spicy dialogues, it has made up for in donations. To date, over $14 million has been spent by the campaign and affiliated outside groups, an astronomical figure for most any congressional campaign but particularly so for a district whose largest city, Covington, has a population of fewer than 50,000.
A vast majority of that sum has gone to negative ads and mailers that have branded Mr. Massie an obstructionist to the Trump agenda and an ally of Democrats.
One A.I.-generated ad showed a likeness of Mr. Massie and two progressive Democrats, Representative Alexandria Ocasio-Cortez of New York and Representative Ilhan Omar of Minnesota, holding hands while checking into a hotel together.
“It’s made a dent,” Mr. Massie conceded of the Gallrein campaign’s fusillade. “They have definitely damaged my image in the district. Fifteen million dollars of negative ads leaves a mark, OK?”
To the surprise of many, the Massie campaign has nearly matched his opponent’s war chest with a prodigious fund-raising effort. But while the online “Massie Moneybomb” appeal has relied on donations averaging about $100, Mr. Gallrein has received checks ranging from $250,00 to $1 million, via a high-dollar political action committee funded by three billionaires animated by Mr. Massie’s votes against aid to Israel: John Paulson, Paul Singer and Miriam Adelson.
A Republican Family Feud
Mr. Massie is not without resources of his own. In campaign ads, he has condemned “woke Eddie Gallrein” for “abandoning President Trump’s Republican Party” by changing his party affiliation to “independent” after Mr. Trump became the nominee in 2016 and waiting until Joseph R. Biden Jr. took office in 2021 before rejoining the G.O.P.
Mr. Massie has also emphasized that he sides with Mr. Trump “a whole lot more than I disagree with him.”
In the closing days of his campaign, he has been joined by Senator Paul as well as a fellow conservative firebrand, Representative Lauren Boebert of Colorado.
In a statement posted on X on Friday, Ms. Boebert said that she supported both Mr. Massie and Mr. Trump. “And if that makes you angry, bless your heart.”
Mr. Trump responded by calling her “Weak Minded” in his own social media post in which he threatened to unendorse her.
“It’s like watching Mom and Dad getting a divorce,” said Mr. Reed. “You just wish they’d come back together. I think this race is really ripping our party apart.”
Robert Draper is based in Washington and writes about domestic politics. He is the author of several books and has been a journalist for three decades.
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