Thomas Massie's Chances of Defeating Trump and the Billionaires
Representative Thomas Massie is set to face off against Trump-backed challenger Ed Gallrein in the Republican primary for Kentucky's 4th Congressional District next week and polls show a close race for the solidly conservative seat.
Massie is one of the most conservative members of Congress but has been at odds with President Donald Trump over foreign policy and the Department of Justice's handling of the Epstein files. The clash, amplified by the involvement of wealthy conservative donors, highlights a deeper struggle over the future direction of the Republican Party.
Trump's endorsements have historically carried significant influence in Republican primaries, particularly among the party's conservative base. But the upcoming May 19 primary will test the power of Trump's influence as his national approval rating wanes.
Newsweek reached out to the Massie and Gallrein campaigns for comment via email.
Thomas Massie vs. Ed Gallrein: What Polls and Prediction Markets Show
The GOP primary enters its final stretch this weekend as Massie and Gallrein work to turn out their base of supporters to the polls. The race is viewed as competitive, with recent surveys suggesting a tight contest.
Todd Belt, director of the Political Management Program at George Washington University, told Newsweek that Trump's endorsement has made Massie vulnerable.
"This is becoming the most expensive House primary race this cycle, and with that kind of money, you can never be certain," he said. Trump is "very powerful" and can "use his endorsement and fundraising capacity to purge the party of those he finds disloyal."
Gallrein led the latest poll from Quantus Insights. It found that 53 percent of respondents planned to support him, compared to 45 percent who planned to vote for Massie. Only 2 percent were undecided. It surveyed 908 likely voters May 11-12 and had a margin of error of plus or minus 3.3 percentage points.
The pollster noted that Massie holds a "durable base" but that Gallrein still holds a lead on both the initial ballot and when leaners are pushed.
"In a nationalized Republican primary shaped by Trump's endorsement, outside spending, and Massie's independent brand, Gallrein enters the final stretch with the advantage," the pollster wrote.
Shauna Reilly, a political scientist at Northern Kentucky University, told Newsweek that there has been a "shift" toward Gallrein in the past few weeks amid polling showing his surge and an increased ad buy in the district.
"This is the first significant challenge that Massie has faced either in a primary or general election,” she said. “I have no doubt of the connection between his opposition to President Trump’s agenda is part of that drive."
The race could be seen as a referendum on Trump or a "cautionary tale for folks who want to oppose his agenda or stand up to him," Reilly said.
"Should Massie lose, it will be clear that Trump still has a hold on the Republican Party even in the twilight of his presidency," she said.
An earlier Quantus Insights gave Massie a lead but found a larger number of undecided voters. It found Massie with 47 percent support to Gallrein's 38 percent, while 14 percent said they were undecided. It surveyed 438 likely Republican primary voters April 6-7 and had a margin of error of plus or minus 4.4 percentage points.
Meanwhile, a Big Data Poll survey gave Massie a nearly 5-point lead. Massie received support from 52.4 percent of respondents, while 47.6 percent said they would vote for Gallrein. It surveyed 433 registered likely voters April 3-7, with a sampling error of plus or minus 4 percentage points.
The poll's director, Rich Baris, wrote in the memo that the district, which is based around Northern Kentucky and includes the suburbs of Cincinnati, is "known for its independent streak."
Massie is favored in prediction markets. He has a 64 percent chance on Kalshi and a 65 percent chance on Polymarket of defeating Gallrein in the primary.
Prediction markets allow traders to buy and sell contracts tied to political outcomes and current events, aggregating real‑money wagers into probability estimates.
Prices fluctuate as traders react to polling, fundraising, candidate developments and broader political trends. They measure trader sentiment at a given moment but do not always accurately predict the future.
Whoever wins the primary will be the significant favorite against a Democrat in the general election. The district is solidly Republican, backing Trump by more than 35 points in the 2024 presidential race.
Billionaires Fund Expensive Kentucky House Primary
The high-profile contest has drawn significant spending, with several billionaires investing in the race. According to The Cincinnati Enquirer, billionaires Paul Singer and John Paulson have donated to a pro-Gallrein PAC called MAGA KY. Meanwhile, the Preserve America PAC, funded by billionaire Mirian Adelson, also donated to the PAC.
Massie has support from one billionaire, as well, with businessman Jeff Yass donating to the Protect Freedom PAC, which has funded the pro-Massie Kentucky First PAC, according to the newspaper.
The pre-primary Federal Election Commission (FEC) filing by Massie's campaign showed that he has raised $5.5 million in the campaign. Gallrein's campaign reported nearly $3.2 million total receipts in the pre-primary filing.
Trump and Massie’s Fallout Explained
Trump has long had a rocky relationship with Massie, whose libertarian-leaning principles have not always meshed well with Trump's MAGA style of politics. Their first major clash came in March 2020 after Massie voted against the Save Our Workers Bill, a $2 trillion COVID-19 relief package. Trump called him a "third rate Grandstander," urging the GOP to "throw Massie out" of their party in a post to X, then known as Twitter.
By the 2024 presidential race, their relationship had improved, with Massie endorsing Trump's campaign.
He said Trump would "put Americans first by securing our liberties at home and preventing needless wars abroad" and "make America Healthy Again by empowering small farmers and taking on special interests that have corrupted our healthcare system" in a statement widely reported in October 2024.
But their relationship has since deteriorated. D. Stephen Voss, professor of political science at the University of Kentucky, previously told Newsweek that the fallout occurred as Trump "shows little tolerance for dissent, including when it’s motivated by conservative principles."
"By the time the Epstein files started stealing headlines, Trump had targeted Massie so many times that it just made sense for the congressman to take the gloves off and fight back," he said.
Massie has voted against parts of Trump's agenda, including the One Big Beautiful Bill Act, which Congress passed last year. Known for a more Libertarian approach to global affairs, Massie has also opposed Trump's foreign policy actions, including military strikes on Iran. He supported a War Powers Resolution aimed at curbing Trump’s ability to declare war on Iran.
The Iran war threatens to be a challenge for Republicans this year, as polls show it is unpopular. It has sent global oil prices surging, leading to higher gas prices for Americans, doing little to quell concerns about inflation and the high cost of living.
Massie led an effort alongside Democratic Representative Ro Khanna of California to force the Justice Department to release the files related to Epstein, a sex offender and disgraced financier who died by suicide in a New York City federal jail in 2019 while awaiting trial on charges of sex trafficking.
Belt pointed to the Epstein files discharge petition as a key turning point in their relationship.
"Trump can’t handle anyone in his party not falling in line-just ask the state legislators in Indiana who didn’t support redistricting," he said, referring to Trump-backed challengers unseating five GOP incumbents in the primary election early this month.
Trump has repeatedly attacked Massie on social media.
"I predict that ‘Representative' Thomas Massie will go down as the WORST Republican Congressman in the long and fabled history of the United States Congress, even worse than Crazy Liz Chaney [sic], Cryin' Adam Kinzinger, and Marjorie "Traitor" Brown (Remember, Green turns to Brown under stress!). They are all misfits and losers, but Massie, who is running against a great American Patriot in the Kentucky Primary, will hopefully lose BIG," Trump wrote on March 11.
Trump has been a vocal proponent of Gallrein, a farmer and veteran who has garnered support from other prominent Kentucky Republicans such as Representative Andy Barr. Senator Rand Paul is backing Massie.
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This story was originally published May 17, 2026 at 5:00 AM.