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March 5, 2026
Al Olszewski insists he saw it coming.
As the rest of Montana was gasping at news that U.S. Rep. Ryan Zinke, and later U.S. Sen. Steve Daines weren’t seeking reelection, Olszewski was scrambling to register his candidacy for the state’s Western U.S. House District. The former Kalispell legislator, who narrowly lost to Zinke in the 2022 primary, needed to get in front of Zinke’s anointed successor, conservative talk show host Aaron Flint.
“My general consultant, who ran my campaign against Ryan Zinke, had heard this rumor a year ago in Washington D.C.,” said Olszewski, a three-time federal office seeker and orthopedic surgeon who goes by ‘Dr. Al.’ “My team has been ready to go, and we were planning to push the button at three o’clock. Less than 48 hours to go and every other incumbent has filed, but he hasn’t filed yet? This was highly unusual.”
The record shows that it was “Dr. Al” who filed first. Zinke posted his retirement announcement on his campaign website shortly before 1 p.m. on Monday. Olszewski got his candidacy officially registered with the secretary of state’s office at 3:22 p.m. Flint wouldn’t file until the following morning, but at the moment of Zinke’s Monday mic drop, Flint rolled out a polished campaign ad and endorsements from Montana’s Republican political elites: Zinke, Daines and Gianforte. And he has a super PAC.
When Montana Secretary of State Christi Jacobsen, who has been touting her relationship with Trump, launched her bid Tuesday, Flint one-upped her with his own Trump endorsement.
Could anything top that? Yep.
On Wednesday, just minutes before the 5 p.m. filing deadline, two-term U.S. Sen. Steve Daines also withdrew his reelection bid. It was surprising, in part, because Daines seemed to be operating at peak power. He chaired the National Republican Senatorial Committee in 2024 when the GOP took back the Senate. And he managed to oust former Democratic Sen. Jon Tester in the process by recruiting current U.S. Sen. Tim Sheehy, also a newcomer, who beat Tester by 46,000 votes. Except for Max Baucus, no Montana senator elected since 1988 has lasted more than 18 years.
Not to be outdone, Sheehy also had quite a week, as a video of him contributing to the removal of a protester from a Senate confirmation hearing turned him into a trending keyword.
Open Senate seats are rare in Montana. The state hasn’t had one since 1977 when Democrat Mike Mansfield retired as Senate majority leader. By keeping his plans secret until it was too late for anyone else to file, Daines effectively boxed out experienced politicians. He also paved the way for his chosen successor, Kurt Alme, a consummate Republican worker bee who had never been a candidate.
“When King Daines and when King Zinke decided that they get to anoint the prince, everybody in Montana doesn’t like that, Republicans, Democrats, independents,” said former Democratic Gov. Brian Schweitzer in an interview Wednesday night. “Let me be clear about something. It is too late to file as a Democrat or as a Republican. And obviously Daines knew that all the way down to the last 20 seconds.”
Zinke, he observed, was pulling off something similar — with a bit more warning.
Who are the anointed ones? And do they have anything in common?
Former Kalispell Mayor, Republican Tammi Fisher, tells Capitolized that Gov. Greg Gianforte is the common denominator. Both Flint and Alme worked for Gianforte. Flint worked for the governor when Gianforte served in the U.S. House. Alme served as budget director.
But they couldn’t be more different. Alme is a Crescent wrench of a Republican servant, best known as revenue director for former Gov. Judy Martz and Trump’s pick to be Montana U.S. Attorney for both of Trump’s presidential terms.
Alme was also president and general counsel for the Yellowstone Boys and Girls Ranch, a nonprofit children’s mental health organization. Before returning to the U.S. DOJ, Alme worked for the National Christian Foundation as executive president for planned giving. NCF reports having distributed $14.5 billion since 1982 through donor advised funds to groups aligned with its Christian ideology.
Like Daines and Gianforte, and Martz, Alme is a Christian conservative, not a MAGA, not a Tea partier. He’s the soft riding Lincoln Navigator to shock jock Flint’s Ford F-150.
“I would classify [Alme] as a pretty traditional right of center, Reagan Republican, 10 or 15 years younger than me,” said Jeff Essmann, former legislator and former Montana Republican Party chair. “Obviously good judgment. And I think a great heart, a good heart.”
Both Essmann and Alme live in Billings. Essmann said that the night Daines withdrew, Alme called Essmann for advice. Essmann said it didn’t sound like the plan for Alme to run was more than a couple days old.
“I urged him to look people in the eye and tell them the truth. It’s always good advice,” Essmann said. “I made a couple recommendations about who he should be working with in a campaign. I asked him, ‘When did this all go down?’ And he said, ‘Well, we’ve had a busy couple of days.’ I believe that’s the truth. I think it was a last-minute decision by Steve. And I think the proof of that is the contrast between Aaron Flint’s rollout, which was polished complete and had been in the works for a while, versus what happened yesterday in terms of Kurt entering the race 10 minutes before the filing closed.”
In contrast to Alme, Flint is well known. His program “Montana Talks,” is the one of the most widely distributed talk radio shows in the state and a mainstay of the conservative culture. It’s not uncommon for someone to call into Flint’s show and suggest that a specific legislator, if listening, call in and join the program. Within minutes, the legislator is often on the line.
Flint’s guests range from state lawmakers to U.S. House Speaker Mike Johnson and Agriculture Secretary Brook Rollins. There is a sentiment in conservative circles that liberals don’t recognize the clout that someone like Flint packs. The person he’s compared to frequently is former Republican U.S. Sen. Conrad Burns, a farm radio man who snuck up on the liberal townees in 1988 and unseated Democratic U.S. Senator John Melcher.
“Aaron Flint is obviously of the Conrad Burns mold,” Essmann said. Burns had “been working the rubber chicken circuit, speaking at every FFA and Farm Bureau awards ceremony in every county across the state for decades, everybody knew him.” Flint works the same circuit.
Flint, a former local TV journalist, was working for Burns on Sept. 11, 2001. He enlisted in the ROTC at the University of Montana, his alma mater, and then went to Iraq as a reservist. He has two Bronze Stars.
In addition to Burns, he worked in the congressional offices of both Gianforte and Zinke. His wife, Jessica, is a former Daines employee, who also worked for Burns and former U.S. Rep. Denny Rehberg. She is currently the representative civil rights advocate for the state Criminal Justice Oversight Council. Her appointment drew controversy because she replaced a representative of the ACLU. Jessica Flint handles communications for Alliance Defending Freedom, a conservative legal organization that “advances every person’s God-given right to live and speak the truth.”
Candidate Flint’s opening campaign ad echoes his talk radio show rhetoric.
“Donald Trump is doing a great job, but radical politicians like AOC, Mamdani and Bernie, they’ve taken over Washington. But here’s the deal, they’re coming for Montana next, sanctuary cities, boys in girls’ sports, public lands being fenced off, locals priced out, and our way of life being pushed aside.”
Will this type of commentary win him the Republican votes he needs? Jeremy Johnson, political scientist at Carroll College, is not so sure. The radio barbs that have fueled Flint’s popularity may also offend some.
“It’s kind of a two-edged thing, right? You become known as a radio host, but you also make enemies that way too,” he said.
–Tom Lutey
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