President Donald Trump’s yearslong revenge tour against select members of his own party faces big tests in May as Trump looks to oust multiple Republican lawmakers who have crossed him in the past.

Primaries in Kentucky, Indiana and Louisiana are the president’s best chances at beating Republican apostates on issues from redistricting to Jeffrey Epstein to impeachment, as he looks to further tighten his stranglehold on the GOP. Trump has issued endorsements in a slew of races, and he and his political machine encouraged some candidates to run and others to drop out, deployed top lieutenants to outside groups and spent millions of dollars on the airwaves.

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“I don’t know if I would nickname it,” a Trump political adviser said about the idea of a “revenge tour.” “But the president and many people around him have been very clear what happens to those who do not stand up for his agenda.”

These include state legislators in Indiana who stood up to Trump on redistricting and Sen. Bill Cassidy, R-La., who voted five years ago to convict Trump on impeachment charges. But few people fit that description more than Rep. Thomas Massie of Kentucky, who is in the toughest fight of his political career: a primary against Trump-backed Ed Gallrein, a former Navy SEAL.

Massie suggested the effort to take out lawmakers who oppose the president has a chilling effect on GOP lawmakers in Congress, noting in a recent interview that Republicans who might be inclined to vote against Trump are afraid to become the president’s next target.

“They tell me that. I mean, they’ll tell me to my face while we’re voting,” Massie said. “They’re like, ‘Well, you’ve got the right vote here, but, you know, this is not a hill I’m going to die on.’”

Massie believes his colleagues are watching his race closely: “They’re trying to decide, could they win an election?”

The seven-term congressman believes they’ll feel freer to cross Trump if he wins. But in the meantime, he’s going it alone.

“If 10 of them would go over the wall with me, the resources would be split 10 ways, and we would, all 10, survive easily,” Massie said, describing a scenario in which Trump allies were forced to play in more House primaries rather than just one in Kentucky. “But because I’m the only one over the wall, all of the ire — and with the exception of, like, the Indiana state Senate and Bill Cassidy, there’s nobody in the House that’s gone over the wall with me. They’re all toeing the line. And that’s why they’re trying to take me out.”

“If I win, it means we have a legislative branch again that can function independently,” Massie said.

Sam Markstein, the national political director for the Republican Jewish Coalition, which is opposing Massie, said Massie’s suggestion that primaries have a chilling effect on the conference was “almost laughable.”

“Republicans that are representing the people of their districts who wildly and overwhelmingly support President Trump and his agenda, they are in a position to win all of their elections,” Markstein said.

May tour stops

The first stop on Trump’s revenge tour will be May 5 in Indiana, where Trump has endorsed primary challengers against seven of the eight GOP state senators on the ballot who opposed the president’s push to redraw state congressional lines and boost Republicans in this year’s battle for the House.

Next, on May 16, Cassidy will fight for the GOP nomination for his seat against Trump-backed Rep. Julia Letlow and state Treasurer John Fleming. Cassidy is one of seven GOP senators who voted to convict Trump during his 2021 impeachment after the Jan. 6 Capitol riot. Four of those seven have since left the Senate.

And, perhaps fittingly, the revenge tour culminates with Massie’s race on May 19.

Trump and Massie have feuded on and off for years. Most recently, Massie opposed Trump’s sweeping tax cut and spending legislation dubbed the “big, beautiful bill.” Massie has also opposed the war in Iran, and he led the effort that forced the Justice Department to release files related to the late sex offender Jeffrey Epstein, which at the time was against Trump’s wishes.

“He views Thomas Massie in a way that compares to few others. [Trump] has skin in the game in a lot of races over the primary season, but few mean as much as that Massie fight,” said the Trump adviser. “He always wants to win, but this is different.”

That has spawned a concerted outside effort to take on Massie, led by senior Trump political adviser Chris LaCivita, who is running the super PAC MAGA KY. The group has spent more than $3 million on ads attacking the congressman, according to the ad-tracking firm AdImpact.

Trump was also involved in recruiting Gallrein, who told The Washington Post that he met with Trump in the Oval Office in October and that the president said “he needed me to run.”

Gallrein’s résumé as a military veteran, combined with the well-funded outside effort, have given Massie’s opponents their best shot yet at defeating him.

“Thomas Massie’s in the political fight of his life,” said Markstein, adding that Gallrein is “shoulders above” the congressman’s previous primary challengers. The Republican Jewish Coalition has opposed Massie in past elections and spent more than $4 million on ads against him in this race.

Ads and pressure campaigns

As loyalty to the president has defined GOP primaries in the Trump era, Trump himself has dominated the airwaves in Massie’s race and the other contests in Indiana and Louisiana, with 70% of TV ads in those races mentioning the president by name, according to an analysis of television spots tracked by AdImpact.

Even candidates Trump is trying to defeat are invoking him in their ads.

Cassidy, the senator facing a Trump-backed challenger, name-checked the president in a recent ad that featured one supporter saying Cassidy “worked with President Trump to pass tax cuts.”

Indiana state Sen. Linda Rogers has a TV ad that says she worked on “extending President Trump’s big, beautiful bill to Indiana,” even though Trump has endorsed her primary challenger, physician Brian Schmutzler.

Outside groups have spent more than $6 million on ads against the seven Indiana state lawmakers Trump is opposing after his redistricting push there failed, according to AdImpact. Two of the major groups, Hoosier Leadership for America and American Leadership PAC, are overseen by Andrew Surabian, a top adviser to Donald Trump Jr. and Vice President JD Vance.

Trump’s team was also actively involved in encouraging — and discouraging — candidates in the Indiana races, bringing several contenders to the White House in early March. Photos of these candidates and the president have popped up in ads and mail pieces. Trump’s political team also actively pressured a candidate to drop out of a primary to avoid splitting the anti-incumbent vote in one district, though that candidate stayed in the race.

In Louisiana, Fleming, the third major candidate in the Republican Senate primary, told NBC News that someone “around” the Trump administration offered him a job as an enticement to drop out, which could have eased Letlow’s path against Cassidy. Fleming declined to disclose other details. If no candidate wins a majority of the primary vote on May 16, the race heads to June 27 runoff between the top two finishers.

Trump endorsed Letlow in the race and encouraged her to run. The president also appeared in a TV ad from an outside group called the Accountability Project saying directly into the camera that Letlow has his “complete and total endorsement.”

But aside from the TV ad, Trump’s orbit does not appear as invested in the race against Cassidy, especially compared to the onslaught that has been unleashed against Massie.

“There is no way he views Cassidy and Massie the same,” Trump’s political adviser said, noting the president has done very little to try and sway the race or attack the three-term senator.

Cassidy has noted on the campaign trail that he broadly supports Trump’s agenda. When asked at an event this month if he regrets his 2021 impeachment vote, Cassidy said he makes his decisions based on the information he has at the time.

“A subtext of this is, how well do I work with President Trump? I work really well with President Trump,” Cassidy said. “I voted with President Trump over 90% of the time in his first term.”

Letlow, meanwhile, recently told NBC News that Trump’s endorsement “has been a huge source of energy for our campaign.”

But some of Letlow’s allies are frustrated that the president has not done more to boost her in the race. And they’re concerned that the president is focused more on Cassidy losing and is agnostic about whether Letlow or Fleming ends up beating him.

Cassidy and an allied super PAC have dominated the airwaves in the meantime, providing a test for whether Trump’s endorsement alone can be enough for a primary challenger to sail to victory — or if that endorsement also has to come with a well-organized, well-funded outside effort.

“His name and endorsement still has good pull,” said one senior GOP strategist. “The problem is, it’s gotten really expensive to let people know about it.”

Devoting the party’s precious resources to primaries in places the GOP is all but guaranteed to win in November is frustrating some Republicans, who want the president to be more focused on battleground House and Senate races, the strategist said.

Republicans are increasingly concerned about their midterm prospects, particularly amid the Iran war and the president’s struggles on the economy. And while the White House has suggested that Trump will hit the campaign trail, his involvement so far has varied.

Most recently, the president stayed on the sidelines as Republicans tried to block a redraw of Virginia’s congressional lines. Trump just held a tele-rally on the eve of the election, which Republicans ultimately lost.

Markstein, of the Republican Jewish Coalition, dismissed concerns that these primaries were drawing focus and resources away from key battlegrounds.

“We will absolutely have the resources necessary to play in several key battleground races,” he said.