The latest test of President Donald Trump’s enduring hold on the Republican Party will be on full display in Kentucky on Tuesday night as Rep. Thomas Massie, R-Ky., fights for his political life in a race that has become a proxy war against the sitting president.

Massie is locked in a tight fight to be reelected to his ninth term as he attempts to head off a challenge from a Trump-backed candidate in what has become the most expensive primary race in U.S. history. Trump has personally gotten involved in the fight, repeatedly telling voters in Kentucky’s 4th District to throw Massie out of office.

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“Thomas Massie is a disaster for our party,” Trump told voters during a campaign event in March. “He comes from a state that I won by a landslide. We got to get rid of this loser. This guy is bad. He’s disloyal to the Republican Party.”

This isn’t the first time Massie has faced a primary challenger. But it is the first time he has faced a real threat.

Rep. Thomas Massie, R-KY, speaks to reporters after a Kentucky Educational Television (KET) debate, Monday, May 4, 2026, in Lexington, Ky. | Jon Cherry, Associated Press

While Massie says his internal polling shows him in a dead heat with retired Navy SEAL Ed Gallrein, who has Trump’s endorsement in the race, some public polls show Gallrein ahead.

Massie has tried to position himself as a political outsider unafraid to break with party leadership, a reputation that has thrust him into the crosshairs with Trump over the last year and a half.

The Kentucky Republican voted against Trump’s massive tax package last summer, the centerpiece of the president’s agenda. He has also opposed military action in Iran despite the president defending U.S. operations.

But the final nail in the coffin was likely Massie’s role spearheading the effort to release all of the Justice Department’s files on convicted sex offender Jeffrey Epstein — something Trump tried to write off as a hoax and a waste of time.

That effort has also split congressional Republicans, as some of Massie’s colleagues joined him on the campaign trail over the weekend to endorse his reelection, much to Trump’s dismay. At least one Republican, Rep. Lauren Boebert of Colorado, was condemned by Trump for supporting Massie’s bid, and he even went so far as to call on someone to challenge her for reelection.

Rep. Thomas Massie, R-KY, exits the studio after a Kentucky Educational Television (KET) debate, Monday, May 4, 2026, in Lexington, Ky. | Jon Cherry, Associated Press
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“I support both of these men,” Boebert wrote in a social media post afterward. “And if that makes you angry, bless your heart.”

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Massie’s bid will be the latest test of Trump’s hold over the Republican Party after successfully ousting Sen. Bill Cassidy, R-La., who lost his primary on Saturday.

Cassidy came in last in a three-way race for the Republican nomination, failing to qualify for a run-off next month. He was defeated after Trump-endorsed Rep. Julia Letlow and state Treasurer John Fleming notched the top two spots.

That has put Trump on a winning streak, especially after ousting a number of state lawmakers in Indiana who opposed his bid to redraw its congressional map to notch more Republican wins in the midterms.

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