With one weekend and a day before the Kentucky primary elections, Rep. Thomas Massie (R-Ky.) has found himself with fewer and fewer friends and allies as President Donald Trump has actively sought to primary him over a number of open disputes.
Massie, who has served in Congress since November 2012, faces three Republican challengers in next week’s primary voting to decide who will be the Republican contender to serve Kentucky’s 4th congressional district in the House. They are: Trump-endorsed former Navy SEAL Ed Gallrein, Dennis Jackson, and Robert Wells. Trump went so far as to attend a rally in support of Gallrein.
This isn’t just a petty dispute between politicians. When Trump tried to get his “One Big Beautiful Bill” passed in 2025, Massie was one of two Republican congressional reps who voted against it. When Trump authorized military action to prevent Iran from getting a nuke, Massie co-sponsored a bill, and he voted for a “bipartisan” resolution to limit Trump’s war powers. Even back in 2020, at the height of the COVID-19 pandemic, Massie stymied Trump’s efforts to fund a $2.2 trillion relief bill.
Through it all, Massie has framed himself as “the principled one” in Congress. My colleague Scott Pinsker nailed it when he summed up Massie’s schtick:
Rep. Thomas Massie (R-Ky.) built his brand on being so dedicated to transparency, integrity, and libertarian values that not even the president of the United States could get him to budge. Love him or hate him, Massie lives by a moral code: He believes what he believes, and if you don’t like it, too frickin’ bad.
And for a very long time, this brand identity kept his congressional seat safe. Even as he (repeatedly) infuriated the Republican Party by voting against key bills and policies, most conservatives shrugged their shoulders, figuring, ‘Sure, it’s a shame Massie didn’t support it, but we’ve gotta respect his heartfelt convictions… right?’
But that’s the problem with schticks, isn’t it? At some point, you start to repeat the schtick, and then people start to realize it’s not about the principle at all – in fact, it’s never been about the principle. Rather, it’s always been about you and getting attention for yourself.
Once the voters get wise to this, you’ve pretty much dug yourself into a deep hole. Everyone can predict you now, and worse, they know exactly why they can predict you. When this happens in Washington, friends and allies start to distance themselves from you.
So who does Massie blame for all of this? Himself? No. Does he blame Trump? Sort of, but not this time. Would you be surprised if I said Israel?
Thomas Massie claims Israel is trying to buy his seat in Congress: “By the time this is over, they will probably have spent $20 million and come up short.” pic.twitter.com/WWnHXYMOBz
— TheBlaze (@theblaze) May 15, 2026
Massie has lost a lot of people who might have had his back. Marjorie Taylor Greene cut her time in Congress short when she realized she had hit her own self-imposed glass ceiling by taking on the president. Her actions since leaving Congress have been telling as well. These are decisions you don’t make hastily or in a huff over a principled political dispute. In any event, she’s gone.
One of Massie’s longtime allies in Washington has been Sen. Mike Lee (R-Utah), who endorsed Massie in 2012 when he first ran for Congress. Lee, a major conservative stalwart and ally of the president’s, has not publicly endorsed Massie this year as he has in the past.
Massie does still have a friend in Rep. Lauren Boebert (R-Colo.). On X, Boebert shared a selfie of her with Massie, while trying to appease the president at the same time, sharing a photo she took with Trump.
Below is my friend Thomas Massie. He loves America and is fighting to save it.
Also below is my friend and President, Donald Trump. He’s put his life on the line to save this great country.
I support both of these men. I’ve worked with both to preserve freedom and liberty.… pic.twitter.com/i1lkTfO9V4
— Lauren Boebert (@laurenboebert) May 15, 2026
Below the “Show More” line, she wrote, “And if that makes you angry, bless your heart.”
You don’t have to work very hard to read between the lines here. The two pictures were for public consumption to make you think she’s trying to play both sides and be the neutral middle. She knows Trump well enough to know that if you’re not with him, you’re against him. So, she has to know that when he sees this post (and he will), it will make him angry.
The only question for Trump is: How angry at her can he afford to be? He needs every Republican vote he can get in this Congress and the next. Her primary doesn’t happen until late June, and she has no serious opposition. Trump will not alienate Boebert at this point. He can’t afford to. So when Boebert says, “Bless your heart,” she’s talking to Trump and pretty much all of MAGA. And she knows how it will be received.
We get the message, Lauren. You don’t need to say it again. You picked a side in this dispute, and it very well may be the losing side.
Meanwhile, Boebert will be campaigning with Massie in the home stretch.
I’ll be in Shelby and Oldham County tomorrow with @laurenboebert and @tichenor4ky.
Hope to see you there!
There will be a surprise endorsement announced! pic.twitter.com/wEZB6VpRgc
— Thomas Massie for Congress (@MassieforKY) May 14, 2026
English poet John Donne is the one who wrote in 1624, “No man is an island.” He could have added that no congressional rep is an island, even if she isn’t being primaried, and Trump may need her for the rest of his term.
Still, with all of the success the Republicans have had with redistricting efforts of late, there is a reasonable chance that the Republicans could end up with enough of a majority in Congress that Trump may not have to cater to Boebert.
If that’s the case, she may still have her seat, but she will no longer be a rising star. Since I’m so far outside the Beltway, I can’t even speculate on what her options may be when her time in Congress is up, but I’m sure she already has a sense of what she’ll do next. The only question is, how long will it be before she eventually follows Marjorie Taylor Greene to greener pastures?
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