Annabelle Gordon | Reuters
This month alone Trump has successfully led the charge to oust a group of Indiana state Republicans who opposed his redistricting push, and helped end the reelection bid of Sen. Bill Cassidy, a Louisiana Republican who voted to convict Trump in his second impeachment.
Now Trump has his sights set on Massie, the Libertarian-leaning Republican with a fierce independent streak, who will face off on Tuesday against Ed Gallrein, a former Navy SEAL who was recruited to the race by the president.
Massie is an anti-abortion rights, pro-gun, fiscal conservative known for wearing a homemade debt clock on his lapel around the Capitol. But he has bucked the president on the release of files related to sex offender Jeffrey Epstein and regularly votes against GOP priorities. Trump wants him gone.
“The worst Congressman in the long and storied history of the Republican Party, is Thomas Massie. He is an obstructionist and a fool. Vote him out of office tomorrow, Tuesday. It will be a great day for America! President DJT,” Trump posted to TruthSocial on Monday, the latest in a series of attacks the president has aimed at Massie in the last few days.
Trump’s approval ratings have plummeted in recent months as prices rise in response to the Iran war, and GOP defectors in Congress have at times bucked the president on tariffs and foreign policy ahead of November’s pivotal midterm election. Republicans are trying to defend slim majorities in both the House and Senate.
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 disapprove of Trump’s handling of the job.
The same poll found 85% of Republicans approve of the job Trump is doing, making him influential in primary elections, where he has been doling out endorsements on Truth Social.
“I think every day in a second term you have less and less power. But he still packs considerable punch among Republican primary voters,” said John Feehery, a Republican strategist and former aide to House Speaker Dennis Hastert. “It’s not politically smart to get into fights with the president.”
Massie’s race is the most expensive House primary on record, according to AdImpact, as pro-Trump and pro-Israel groups have poured in money to oust the incumbent. More than $32.6 million has been spent on ads, including $7.9 million targeting Massie.
And it’s taken an ugly turn. One AI-generated ad targeting Massie from MAGA KY PAC accused him of being in a “throuple” with liberal Democratic Reps. Ilhan Omar of Minnesota and Alexandria Ocasio-Cortez of New York.
An attack ad against Gallrein portrays the billionaire donor Paul Singer, who gave to the Trump-backed candidate and is Jewish, with a rainbow Star of David in the background. Singer has a son who is gay.
The Massie and Gallrein campaigns didn’t immediately respond to requests for comment. The White House referred to Trump’s Truth Social posts when asked for comment on the Kentucky race.
In an unusual move, Secretary of Defense Pete Hegseth was on the ground in Massie’s district on Monday campaigning with Gallrein. Sitting Cabinet officials tend not to get involved in political campaigns, and a federal law, known as the Hatch Act, bars cabinet secretaries and other executive branch officials from engaging in political activities in their official capacities.
“Secretary Hegseth is attending this event in his personal capacity. No taxpayer dollars will be used to facilitate his visit,” Pentagon spokesperson Sean Parnell said in a statement. “His participation has been thoroughly vetted and cleared by lawyers, including the Department of War Office of General Counsel, and does not violate the Hatch Act or any other applicable federal statute.”
Massie, meanwhile, has pointed to an influx of money from “the Israeli lobby,” including from the likes of Singer and the billionaire Miriam Adelson, as well as organizations like American Israel Public Affairs Committee. Massie, who is generally against foreign aid, has opposed military aid to Israel and voted against symbolic resolutions in support of the country.
“[The primary]will be a referendum on foreign policy, whether Israel gets to dictate that by bullying members of Congress,” Massie said on ABC News on Sunday. “But you can tell that I’m ahead in the polls and they’re desperate, that’s why they’re sending the Secretary of War to my district tomorrow.”
Recent polling on the race appears to give Gallrein a slight edge, though it will be difficult to unseat a high-profile incumbent who has represented the district for more than a decade.
But Feehery and a second Republican operative, who requested anonymity to speak candidly, both predicted that Massie would fall short for not being sufficiently loyal.
“My understanding of that district is [Massie] is well-liked. He has his own little base of Massie-like people who respect him for sticking to his guns,” the operative said. But the amount of money spent in the race and the quality of Gallrein’s candidacy will be tough for Massie to surmount, the operative said.
“I think it’s going to be pretty hard. I expect him to lose tomorrow,” the GOP operative said.
Feehery concurred. Even as the clock ticks on Trump’s time in power, Massie, like Cassidy, may have taken too big a political gamble by opposing the president.
“At the end of the day if you piss off Trump he’s going to go after you,” Feehery said.