U.S. Rep. Thomas Massie (R-Ky.) speaks at a press conference on the Epstein File Transparency Act prior to the House vote on releasing files on the late convicted Jeffrey Epstein at the Capitol in Washington, DC, on November 18, 2025.
Annabelle Gordon Reuter
After a string of victories in this spring’s Republican primaries, President Donald Trump is preparing for the next stop on his revenge expedition: Kentucky. There, Rep. Thomas Massie, always a thorn in the side of the House Republican leadership and the president, is embroiled in a fierce battle for his political future.
This month alone, Mr. Trump successfully led an attack to expel a group of Indiana Republicans who opposed his redistricting push and helped block the re-election of Sen. Bill Cassidy, the Louisiana Republican who voted to convict Mr. Trump in his second impeachment.
President Trump is now setting his sights on Massey, a libertarian-leaning Republican with fierce independence leanings, and is scheduled to face Ed Gullane, a former Navy SEAL who the president scouted for his campaign, on Tuesday.
Massey is an anti-abortion, pro-gun and fiscal conservative who is known for wearing a handmade debt clock on his chest around the Capitol. But he has opposed the president over the release of files on sex offender Jeffrey Epstein and regularly votes against Republican priorities.
Trump wants him out of office. And on Monday, he began a series of posts targeting Massey.
“The worst Congressman in the long and storied history of the Republican Party is Thomas Massie. He is an obstructionist and a fool. Tomorrow, Tuesday, we will vote him out of office. It will be a great day for America! President DJT,” Trump wrote in one article.
“We’re running against the worst congressman in the history of this country. His name is Thomas Massie, and he’s from Kentucky. We want him out of business tomorrow. He’s really bad,” Trump said in a video posted late Monday afternoon, sitting in the Oval Office.
Primaries like the one in Kentucky on Tuesday are effectively referendums on President Trump’s control over the Republican Party.
President Trump’s approval ratings have plummeted in recent months as prices rise due to his response to the Iran war, and Republican defectors in Congress have at times turned against him on tariffs and foreign policy ahead of crucial midterm elections in November. Republicans are trying to protect their slim majorities in both houses of Congress.
But with two and a half years remaining in his second term, his influence on Republican electoral politics is hard to deny. A recent CBS News poll found that 63% of those surveyed disapproved of President Trump’s handling of his job.
The same poll found that 85% of Republicans approve of Trump’s job, and that Trump has held sway in the primaries and expressed support for Truth Social.
“I think he has less and less power every day in his second term, but he still has a lot of power among Republican primary voters,” said John Feehely, a Republican strategist and former aide to House Speaker Dennis Hastert. “It’s politically unwise to pick a fight with the president.”
Massie’s race will be the most expensive House primary in history, with pro-Trump and pro-Israel factions pouring money into unseating the incumbent, according to AdImpact. More than $32.6 million has been spent on advertising, including $7.9 million targeting Massey.
And it took an ugly turn. One of MAGA KY PAC’s AI-generated ads targeting Massey accused him of having a “threesome” with liberal Democrats Rep. Ilhan Omar of Minnesota and Alexandria Ocasio-Cortez of New York.
The attack ad against Mr. Galine depicts Paul Singer, a Jewish billionaire donor who donated to candidates supported by Mr. Trump, with a rainbow-colored Star of David in the background. Singer has a gay son.
Massey’s and Galane’s campaigns did not respond to requests for comment. The White House referred to President Trump’s Truth social posts when asked for comment on the Kentucky race.
In an unusual move, Defense Secretary Pete Hegseth was campaigning with Garrein in his Massey constituency on Monday. Sitting Cabinet members tend not to engage in political campaigns, and a federal law known as the Hatch Act prohibits Cabinet members and other executive branch officials from engaging in political activity in their official capacity.
“Secretary Hegseth is attending this event in his personal capacity. No taxpayer dollars will be used to facilitate his visit,” Pentagon spokesman Sean Parnell said in a statement. “His participation has been thoroughly vetted and cleared by legal counsel, including the Department of the Army’s Office of General Counsel, and does not violate the Hatch Act or any other applicable federal law.”
Meanwhile, Massey pointed to an influx of money from the Israel Lobby, which includes Singer and billionaire Miriam Adelson, and organizations such as the American Israel Public Affairs Committee. Although Massey generally opposes foreign aid, he opposes military aid to Israel and has voted against symbolic resolutions supporting Israel.
“(The primary election) is going to be a referendum on whether Israel can bully its members of Congress and decide its foreign policy,” Massey told ABC News on Sunday. “But the polls show that I’m ahead and they’re desperate. That’s why they’re sending the army chief to my district tomorrow.”
Recent polls on the race show Galine with a slight lead, but it will be difficult to unseat the prominent incumbent who has represented the district for more than a decade.
But Mr. Feeley and another Republican operative, who requested anonymity to speak candidly, both predicted that Mr. Massey lacked sufficient loyalty and would fail.
“My understanding of that district is that (Massey) is well-liked. He has a small base of people like Massey who respect him for sticking to his guns,” the operative said. But given the amount of money spent on the campaign and the quality of Garlein’s candidacy, it will be difficult for Massey to overcome, the operative said.
“I think it’s going to be a pretty tough fight. I expect him to lose tomorrow,” the Republican operative said.
Feeley agreed. Massey, like Cassidy, may have taken too great a political gamble by opposing the president, even though the clock is ticking for the Trump administration.
“If you piss Trump off, at the end of the day, he’s going to come after you,” Feeley said.
