Trump v Massie: Could president's Republican nemesis survive $20m attack to oust him?

"It's not that you have to agree on every single issue, but at a certain point you've got to look at the big picture and say, how can we move this ball forward?"

If Republicans had a comfortable majority in the House of Representatives, as they did when Massie was first elected to the chamber in 2012, such apostacy might be considered a quirky annoyance. But with his party holding power by the narrowest of margins during Trump's second term, the Kentuckian has become a constant headache – delaying or outright derailing Trump's congressional agenda.

"I just can't stand this guy," Trump said at a Kentucky rally with Gallrein in March. "We've got to get rid of this loser."

On Tuesday, that day of reckoning may arrive. If Massie loses, he would become just the latest in a long line of Republicans who crossed Trump and were subsequently vanquished – by resignation, forced retirement or defeat in Republican primaries.

If Massie survives to face a Democrat in November, however, it could serve as a sign that Trump's power over his party is not limitless. It could stiffen the spines of other congressional Republicans who may be seeking to distance themselves from a president who, while still beloved by many in his party, has sagging overall approval ratings that could be a liability during a general election campaign.

"This race has come down to a Trump versus Massie dynamic," said Shane Noem, chairman of the Kenton County Republican Committee. "It's a 'pick a side' moment for a lot of voters."

To get to this point, Massie has had to walk a fine line. In 2024, Trump won Kentucky's Fourth Congressional District over Democrat Kamala Harris by 35 points. On the campaign trail, Massie and his political allies have tried to emphasise the areas he agrees with Trump and explain away the high-profile breaks.

He has said that Trump has admiringly called him a "tough cookie" in private conversations, punctuating the point with a serviceable impersonation of the president.

"I voted with the party 90% of the time," Massie said during his Shelbyville appearance. "The problem we have is not that I'm voting against the Republican Party up there, it's that the Republican Party up there is sometimes voting against Republican people back home. That's the 10% of the time."

He said that his votes against massive spending packages that contain provisions he opposes meant that critics can attack him for blocking popular measures also in the legislation. But his opposition, he contended, made the final versions of the legislation better.

"The negotiation starts when one person says no," he said. "And if nobody says no, then you get the whole standing pile of crap."

It's a nuanced view that doesn't lend itself to easy explanations – and has opened up Massie to withering attacks from Trump-aligned Republicans, a criticism his allies seek to dispel.

"They don't explain why he voted for smaller government," said congressman Warren Davidson of Ohio, who campaigned with Massie in Florence. "You only get yes, no or present. You don't get an essay."

By comparison, Gallrein's task has been much simpler. He is campaigning almost entirely on being Trump's choice. It's printed on his yard signs. It's featured on his website and at the top of his social media profiles. It's a central fixture in his television and internet advertising campaigns.

"This district is Trump country," Gallrein said when announcing his congressional bid. "The president doesn't need obstacles in Congress, he needs backup."

The former Navy Seal - who owns a farm in Shelbyville with a market cafe, plant store, petting zoo, and pavilion that hosts corporate events – has run a low-profile campaign that borders on invisible. His events are small and seldom announced in advance. He has skipped almost all the scheduled debates and forums with Massie. He declines most media interview requests.

"At the end of the day, Gallrein's best argument is that Trump wants him," said Trey Grayson, who served two terms as Kentucky's secretary of state and is now a Republican strategist. "I think their theory is there are enough folks for whom that's enough that you get to 51%."

They may be right.

Loren Becker, a semi-retired registered nurse, had ducked into the Black Goose coffee shop in Union, Kentucky, to escape a downpour on Saturday morning. He said he admired Massie's independence and willingness to "stand up for what he believes in".

So was he supporting Massie?

"I'm a little bit conflicted," he said after a long pause. "I was very conflicted. I definitely wouldn't be opposed if he ends up in November. And that being said, I did not vote for him."

He said he couldn't abide by Massie's votes against legislation that funded immigration enforcement – one of those big bills that Massie had tried to block.

"That tore me up," he said.

In these final days on the campaign trail, Massie's events have seemed a bit like a collection of misfit toys.

The politicians who joined Massie have all had their clashes with Republican leadership – either in Washington or in local Kentucky politics. There's Boebert, in a black cowboy hat, talking about how she strategised with Massie to handle the intense pressure the White House brought on her to drop her support for releasing the Epstein files.

Indiana congresswomen Victoria Spartz delivered a frenetic Massie endorsement with a thick Ukrainian accent.

"It's very easy to be a rubber stamp, get that cheque, be nice to everyone else and just go along and be re-elected," Spartz said. "It's much harder to say no, guys, that's not what we are elected on. People rely on us, people are struggling, people are really getting hurt."

Senator Paul, one of the original grassroots "Tea Party" conservatives who organised against President Barack Obama and the Democratic congressional majority in 2010, has, like Massie, also bucked his party's leadership.

"We did not come to Congress to join the club," he said. "We did not come for fame or fortune. We came for one purpose, and that is to defend the Constitution."

If Massie's campaign team made for a strange assortment, those in the audience were an even more unusual collection.

Stewart Rhodes, the leader of the fringe right Oath Keepers who was convicted of sedition for his involvement in the 2021 attack on the US Capitol and pardoned by Trump, repeatedly showed up in a Massie campaign T-shirt. Kyle Rittenhouse, who gained notoriety for shooting three protesters during the Black Lives Matters demonstrations in Kenosha, Wisconsin, made an appearance in Florence.

Former congressman Matt Gaetz, who resigned from Congress in 2024 amid a congressional ethics investigation over claims of sexual misconduct, which he denied, interviewed Massie for his show on the right-wing One America News.

He asked the congressman if he was going to run for president in 2028. Massie demurred.

There were blue-blazer-wearing libertarians too young to shave and a tattooed man wearing an "American Reich" shirt.

Dashing around behind the scenes were a team of online influencers and content creators who had travelled to Kentucky from across the country to show their support for Massie, live-streaming all the way.

"We won't tell people in Kentucky who to vote for, but we will tell them where the polls are," said Tiffany Cianci, who drove to Kentucky from Maryland. "We will remind them what's at stake, and we will tell them their vote matters."

In American politics, the stakes can often be measured in dollars – and this Kentucky race is no exception. It has become the most expensive House primary in US history, with more than $32m spent by the candidates and affiliated committees.

As Massie frequently notes, the bulk of the outside money arrayed against him has come from three billionaires – Las Vegas casino tycoon Miriam Adleson and hedge fund managers Paul Singer and John Paulson.

On the stump, Massie calls them "globalists" and notes their past ties to Democratic candidates and issues. Their money has been funneled through Kentucky MAGA, a committee set up by former Trump campaign director Chris LaCivita, and the pro-Israeli lobbying group Aipac, which objects to Massie's opposition to military aid to Israel.

They've inundated the airwaves with negative adverts targeting Massie, including one that used AI to create fake images of Massie checking into a hotel room with Democratic congresswomen Alexandria Ocasio-Cortez and Ilhan Omar – a "throuple" that "betrayed President Trump".

Massie has raised enough money to fight back with his own ad campaign, in part because of his elevated national profile over the past year.

"If he hadn't stood on the principle that the Epstein files ought to be brought out, I doubt anything else he's done would have attracted the sort of national following that would have gotten him the support he needed," said Stephen Voss, a political science professor at the University of Kentucky.

His campaign and affiliated groups have aired ads painting Gallrein as a puppet for the wealthy elite and "woke Eddie", suggesting he was the real closet liberal. One spot placed a rainbow Star of David behind Singer, calling him a "major pro-gay, pro-trans activist".

On the campaign trail, Massie – who has denied accusations of anti-Semitism - has largely avoided talking about Israel, instead focusing on local issues. But in Florence, he joked that Gallrein's phone number "has a Tel Aviv area code".

"I better quit making jokes right here on the spot," Massie quickly said, as the crowd laughed and cheered. "I better try these out on the staff first."

Recent polling suggests the race between Massie and Gallrein is a dead heat.

According to Voss, the nature of the Massie's district – with its more affluent, educated voters in the Louisville and Cincinnati suburbs and fewer of the lower-income, low-propensity voters that Trump brought into the Republican fold – might be more hospitable grounds for a conservative who defies Trump.

In addition, the president's recent polling dip, attributable in part to rising petrol prices and an Iran war that is dividing his base, could bolster Massie's anti-interventionist brand of foreign policy.

Massie's leadership on the Epstein files has let him position himself as an outsider, doing battle against the wealthy and well-connected.

If all that doesn't matter, and Massie is defeated on Tuesday, Trump's grip on the Republican party will remain solid – and his critics among Republican ranks will have all the more reason to watch their words.

"We don't officially have a filter on us," congressman Davidson said, "but everybody knows there are consequences."

But if Massie succeeds, for whatever reason, he will be breaking new ground in the Trump era as a national Republican who fought the president and survived to tell the tale.

"A single house member going against the president of the US and prevailing?" said Grayson.

"That's a tell that maybe you can stand up and get away with it."