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Jon Tester
Donald Trump has his heart set on ousting Sen. Jon Tester. Matthew Brown/AP

There Is One Senate Race Trump Is Very Personally Invested in Winning

“There’s almost nothing that DJT enjoys more than exacting vengeance on his enemies,” a source close to Trump told NOTUS.

Donald Trump has his heart set on ousting Sen. Jon Tester. Matthew Brown/AP

The Montana Senate race is special to Republicans for a few reasons. For starters, it’s the party’s top prospect to flip the Senate, with a vulnerable Democrat running for reelection in a decidedly red state.

But for Donald Trump, he’s not campaigning in a state he won by 16 points just because he wants to extend his margins. He’s going because beating Sen. Jon Tester is personal.

As a source close to Trump put it to NOTUS, “There’s almost nothing that DJT enjoys more than exacting vengeance on his enemies.”

“You screw him today, and you can rest assured that your day is coming,” this source continued. “Might not be tomorrow, might not be next week or next year, but it’s coming.”

Trump’s grudge against Tester goes back to 2018. Back then, Tester, the top Democrat on the Senate Veterans’ Affairs Committee, opposed Trump’s nominee to run the Department of Veterans Affairs. The pick — then-White House physician Ronny Jackson — faced allegations that he inappropriately prescribed pain medication and created a toxic work environment. (Jackson has denied those allegations, but an Inspector General report later substantiated some of the claims.)

Jackson withdrew his candidacy. A livid Trump blamed Tester and called on the senator to resign. And then, when that failed, the former president fought to oust him.

Trump rallied in Montana four times that election cycle to topple the well-liked farmer turned lawmaker. Vice President Mike Pence and Donald Trump Jr. each made multiple trips to Big Sky Country to boost Tester’s opponent, Rep. Matt Rosendale.

Tester won by three and a half percentage points anyway.

But Trump hasn’t forgotten.

Sources familiar with the GOP candidate’s thinking told NOTUS he’s eager for a rematch and is taking the fight back to Tester’s home turf with a Friday rally in Bozeman. He’s even bringing Jackson with him.

Jackson told NOTUS he was attending the rally in Bozeman to support GOP Senate candidate Tim Sheehy and to stand against Tester, who Jackson called “a national embarrassment in the Senate.”

“He portrays himself as a moderate, but is a rubber stamp for Biden/Harris and the disgusting agenda of the progressive left. He does not deserve to represent the fine America First people of Montana. It’s critical we vote out anti-veteran, destructive, boot-licking radicals like two-faced Tester,” Jackson said.

But it’s not just Jackson who despises Tester.

“Trumpworld will never forget what Jon Tester did to Ronny Jackson,” a Trumpworld adviser told NOTUS, “and everyone in the orbit, from Trump on down, are looking forward to getting revenge on him by helping send him into retirement come November.”

Trump Campaign Spokesperson Karoline Leavitt told NOTUS that, “It’s going to get testy for Jon Tester. Stay tuned!”

Trump’s ire adds to the already exorbitant stakes of the Montana Senate race. The contest has long been framed as a must-win for Republicans as they endeavor to reclaim the Senate. Democratic resources are spread around the country as the party stares down a bruising map that features a slew of vulnerable incumbent Democrats in Ohio, Pennsylvania and Nevada battling in costly media markets.

Additionally, Trump and his GOP seem to be learning from their 2018 mistakes. Instead of letting the staunchly conservative Rosendale run again, top Republican brass intervened, recruiting former Navy SEAL and businessman Tim Sheehy.

But even in Trump-loving Montana, Sheehy is no shoo-in. A June memo from the Senate Republican’s campaign arm reported that both Tester and Sheehy are polling at 46% and called the race a “statistical tie.” More recent polling from The Hill has shown Sheehy up 48% to Tester’s 46%, but the results are within the margin of error. It will almost certainly be a tight race.

Just as much as Trump wants to tear Tester down on Friday, he also needs to prop Sheehy up.

“I’m going out to certain places to help certain senators get elected,” Trump told reporters Thursday. “Not even for me. I’m trying to help when I go out to Wyoming, or when I go out to Montana, or I’m going to different places to help people.”

Sen. Steve Daines — a fellow Montanan and the chair of the National Republican Senatorial Committee — told NOTUS in July that Trump understands “the importance” of having a Republican majority and that he and his team have been great partners when it comes to taking back the Senate.

“We really feel like we’re flying as a tight formation. If we were the Blue Angels, we’re in a tight formation of President Trump, the NRSC and even seen some outside groups [Senate Leadership Fund] and so forth,” Daines said. “It seems like we’re all on the same page.”

Trump has already rallied for the GOP candidates in Ohio, Pennsylvania and Nevada, who are running behind him with the apparent hope that rising tides will lift all ships.

But that hope couldn’t be truer than in Montana, where Trump is running 15 points ahead of Vice President Kamala Harris. Armed with a Trump endorsement, Sheehy has been closely aligning his campaign with the former president’s.

“Montana stands with President Donald J. Trump, and I’m proud to stand strong with President Trump in the fight to save America,” Sheehy said in a statement to NOTUS, adding that he plans to campaign with Trump to beat inflation, end illegal immigration and stop taxing tips.

For their part, Democrats have tried to focus the race on local issues rather than national politics. Operatives are highlighting Tester’s long-standing state bona fides and record of deliverables on issues like infrastructure and veterans affairs rather than any beef with Trump.

“Whether it’s today or three months from now, Montana voters will still be choosing between a third-generation dirt farmer who’s worked with Democrats and Republicans (including President Trump) or a living embodiment of every shady, rich out-of-stater who moved to Montana to live out their Yellowstone cowboy fantasies,” Senate Majority PAC spokesperson Sarah Guggenheimer said in a statement to NOTUS.

“And Washington Republicans know it too,” she added.

Trump’s popularity with Montana Republicans, however, is undeniable. The trip to Montana will fire up the MAGA base and give Trump time to attend a swanky fundraiser with North Dakota Gov. Doug Burgum. (Event ticket prices range from $100,000 to $844,600.)

Still, Tester is angling to siphon GOP votes in his own race against Sheehy and is betting on Trump voters splitting their ticket. This week, his campaign launched “Republicans for Tester” with over 100 GOP members, including former Gov. Marc Racicot, who will highlight his experience in Montana.

“No matter who is in the White House, Jon Tester always does what’s right for Montana,” Tester campaign spokesperson Monica Robinson said in a statement to NOTUS.

“It’s why President Trump signed more than 20 of his bills into law,” she said, also emphasizing that Montana Republicans endorsed Tester earlier this week.

The focus on local issues is not to say Tester hasn’t sparred with Trump. In 2018, for example, he caught flack for a Pearl Jam poster depicting the senator flying on a tractor above a White House engulfed in flames with Trump lying dead on the front lawn. (Pearl Jam used the poster to fundraise for Tester, though the senator’s campaign did not give any input on the design.)

“Though the poster was off message,” Tester wrote in his 2020 book, “I didn’t want to admit to her that I actually loved it.”

As Election Day nears, Tester has tacked to the center. He was among the first senators to call for President Joe Biden to withdraw his campaign. He was also the first Senate Democrat to co-sponsor a GOP-led Laken Riley Act that would crack down on undocumented immigrants who commit crimes like burglary or shoplifting.

In a statement to NOTUS, the NRSC would rather keep the conversation on Tester’s two votes for Trump’s impeachment and Pearl Jam poster.

“Tester spent the last five years exposing himself as the radical liberal he is, and I look forward to hearing President Trump’s response,” NRSC spokesperson Mike Berg said.

But it appears this race isn’t primarily about policy for Trump; it’s about pride.

That’s not a new ethos for Trump, who has made no secret of his proclivity for revenge. His Truth Social page is littered with suggestions that he’d seek retribution, open “Pandora’s Box” and bring back “televised military tribunals” against rivals who cross him.

Trump’s mantra has been well-documented: “IF YOU GO AFTER ME, I’M COMING AFTER YOU!” he said in a 2023 Truth Social post.

However, Trump’s mission to remove his enemies from positions of power has only found middling degrees of success. While he was able to take down Rep. Liz Cheney for sitting on the Jan. 6 committee, Sen. Lisa Murkowski — whom Trump vowed to beat in 2022 after she voted for his impeachment — is comfortably serving her fourth term in the Senate.

Tester is another name on Trump’s target list. But the former president’s latest hits against him have been scattershot. At a May fundraiser for Jackson — who is now a U.S. congressman from Texas — Trump said Tester “looks pregnant to me.”

Whether Trump strikes a more pointed tone against Tester on Friday remains to be seen. Plenty of eyes will be on Trump, though, during his first rally since Harris named Minnesota Gov. Tim Walz as her running mate.

The message from the Trumpworld source, at least, is clear: “Jon Tester’s time has arrived.”


Riley Rogerson and Reese Gorman are reporters at NOTUS.