Kentucky Republican Thomas Massie is the next target of Trump’s revenge tour

After a string of wins in the Republican primary this spring, President Donald Trump is preparing for the next stop on his revenge tour: Kentucky, where Rep. Thomas Massie, a perennial thorn in the side of House GOP leaders and the president, is locked in a tough fight for his political future.

This month alone, Trump successfully led the charge to oust a group of Indiana Republicans who opposed his redistricting policy, and helped end the reelection bid of Sen. Bill Cassidy, a Louisiana Republican who voted to acquit Trump of his second impeachment.

Trump is now turning to Massie, a libertarian-leaning Republican with a strong independent streak, who will face off Tuesday against Ed Gallrein, a former Navy SEAL recruited to the presidential race.

Massie is an anti-abortion rights, pro-gun, conservative conservative known for wearing a homemade debt clock on his badge around the Capitol. But he has criticized the president over the release of files related to sex offender Jeffrey Epstein and regularly votes against GOP priorities.

Trump wants him gone. On Monday, he fired off a series of posts targeting Massie.

“The worst Congressman in the long and storied history of the Republican Party, Thomas Massie. He is a obstructionist and a fool. Vote him out of office tomorrow, Tuesday. It will be a great day in America! President DJT,” Trump wrote in another.

“We are dealing with the worst congressman in the history of our country, his name is Thomas Massie, who is from Kentucky. I hope he puts him out of business tomorrow. He is very bad,” Trump said in a video, posted Monday afternoon, while sitting in the Oval Office.

Primaries like Tuesday’s in Kentucky are a test of Trump’s hold on the Republican Party.

Trump’s approval ratings have fallen in recent months as prices have risen over the Iran war, and GOP defectors in Congress have at times charged the president on taxes and foreign policy ahead of key midterm elections in November. Republicans are trying to protect many minorities in the House and Senate.

But with two and a half years left in his second term, his influence on Republican electoral politics is hard to deny. A recent CBS News poll found that 63% of those polled disapprove of Trump’s handling of the job.

The same survey found 85% of Republicans approved of the job done by Trump, which made him influential in the primary election, where he was issuing recommendations on Social Truth.

“I think every day in the runoff he has less and less power. But he still inspires a lot of enthusiasm among Republican voters,” said John Feehery, a Republican strategist and former aide to House Speaker Dennis Hastert. “It is not politically smart to argue with the president.”

Massie’s race is the most expensive House primary in history, according to AdImpact, as pro-Trump and pro-Israel groups poured in money to unseat the incumbent. More than $32.6 million was spent on advertising, including $7.9 million directed at Massie.

And it took a bad turn. One AI-generated ad targeting Massie from the MAGA KY PAC accused him of being “in league” with Democratic Reps. Ilhan Omar of Minnesota and Alexandria Ocasio-Cortez of New York.

The anti-Gallrein attack ad features billionaire donor Paul Singer, who gave to the Trump-backed candidate and is Jewish, with a rainbow Star of David in the background. The singer has a gay son.

Massie’s and Gallrein’s campaigns did not immediately respond to requests for comment. The White House referred to Trump’s Truth Social posts when asked to comment on the Kentucky race.

In an unusual move, Defense Secretary Pete Hegseth was down in Massie County on Monday campaigning with Gallrein. Sitting Cabinet officials tend not to be involved in political campaigns, and a federal law, known as the Hatch Act, prohibits cabinet secretaries and other senior branch officials from engaging in political activities in their official capacity.

“Secretary Hegseth is personally attending this event. No taxpayer dollars will be used for his attendance,” Pentagon spokesman Sean Parnell said in a statement. “His participation has been thoroughly vetted and cleared by attorneys, including the Department of Defense’s Office of General Counsel, and does not violate the Hatch Act or any other applicable federal law.”

Massie, meanwhile, pointed to an influx of money from the “Israeli tourism industry,” including the likes of Singer and billionaire Miriam Adelson, as well as organizations like the American Israel Public Affairs Committee. Massie, an opponent of foreign aid, opposed military aid to Israel and voted against landmark resolutions supporting the country.

“[The primary]it’s going to be a referendum on foreign policy, whether or not Israel can say that by harassing members of Congress,” Massie said on ABC News on Sunday. “But you can tell I’m ahead in the polls and they’re desperate, that’s why they’re sending the Secretary of Defense to my district tomorrow.”

Recent polls in the race appear to give Gallrein a slight edge, though it will be difficult to unseat the incumbent who has represented the district for more than a decade.

But Feehery and a second Republican official, who asked not to be identified to speak candidly, both predicted Massie would fail by not being credible enough.

“My understanding is that region [Massie] you are loved. He has his own small base of people like Massie who respect him for sticking to his guns,” the nurse said. But the money spent on the race and the level of Gallrein’s candidacy will make it difficult for Massie to win, the worker said.

“I think it’s going to be very difficult. I expect him to lose tomorrow,” the GOP operative said.

Feehery agreed. Even as the clock ticks on Trump’s reign, Massie, like Cassidy, may have taken a big political gamble by opposing the president.

“At the end of the day, if you upset Trump, he will come after you,” Feehery said.