'The right path for all Montanans:' Longtime Dem state lawmaker enters eastern district race

Amid two political newcomers competing in the Democratic primary to replace Republican Rep. Troy Downing, one of Montana’s longest-serving Democratic legislators has now entered the race.

Sen. Jonathan Windy Boy of Box Elder, who first ran for the state Legislature in 2003, has won every legislative race he’s pursued since then, alternating between both the House and Senate. After 12 sessions and 40 successful bills and resolutions, he believes his legislative history speaks to work he’s done for his home state when national politics doesn’t. It’s part of why he’s running, he said.

“We’re heading down a path that just isn’t Montana,” Windy Boy said in an interview with the Billings Gazette.

He said politics have become polarized and that current congressional incumbents are contributing to it rather than addressing Montanans’ needs. He described polarization being an issue on both sides.

If Windy Boy wins the primary, his formidable experience at the Legislature will still be weighed by a district that’s shown little support for Democrats in the last two election cycles in which it has existed. Downing won the last eastern congressional district race with 66% of the vote. In 2022, an independent candidate took second place with 22% of the vote over a Billings Democrat.

While his campaign announcement described him as a moderate, he cast doubt on the term. Instead, he called himself a “true Montanan thinking of the right way for the right path for all Montanans, on or off reservations.”

He pointed to the property tax relief Democrats and several Republicans passed last session as an example of putting the state’s interests first.

Alongside Billings, Helena and Great Falls, the eastern district contains five of Montana’s seven reservations. Windy Boy is part of the Chippewa Cree tribe residing on the Rocky Boy’s Reservation. The longest-serving member of the Montana American Indian Caucus, Windy Boy’s passed legislation includes support for the Montana Indian Child Welfare Act, regulations and additional funding for Indian Education for All and bolstered community health efforts.

His past legislation reflects his priorities, he announced in a news release. Those involve a focus on the Native American population, health care, education and tax relief for business and agriculture equipment. He serves as the Chippewa Cree Tribe’s historic preservation officer.

An example of relative ideological independence, in his announcement, Windy Boy described himself as a “pro-life” Democrat. It’s a break from a party that is set on restoring or maintaining reproductive rights after the Supreme Court’s overturning of Roe v. Wade.

“It just shows the values that I was brought up with,” the 67-year-old explained. In his first legislative session in 2003, tribal elders asked him whether he had the same values as they did with his votes on anti-abortion bills.

“And then they asked me, ‘What do you pray for?’ I said, ‘Good health and life.’ And nothing more needed to be said,” Windy Boy said. “And so, as my track record has proved, if a good idea makes sense, then I'll get behind it.”

Similarly, he pointed out how he carried a bill in 2017 to establish public charter schools, traditionally a more Republican cause. In 2023, Windy Boy filed a brief in support of the state’s public charter school law, the only lawmaker to do so at the time.

Windy Boy’s entrance continues a trend similar to the other two Democratic contenders in the race — mostly avoiding the growing unpopularity associated with Democrats that isn’t helped in a majority-red district. Instead, candidates have emphasized independence and focused on policy issues, while quietly running as part of the party.

Democratic contender Sam Lux on his campaign website emphasized that “he doesn’t want to be a politician” who “have too often proven to be corrupt, self-serving and detached from the realities faced by everyday Americans.” Besides the Democratic party’s logo at the bottom of each page, his campaign website doesn’t mention the party a single time.

The other contender, Brian Miller, describes in his campaign bio his time volunteering for Republican George H.W. Bush in high school and his overall respect for that presidency. While he later notes that future campaigns he’s worked on were all Democrats, his bio notes, "today I would consider myself an independent-minded Montanan, as I think both parties have lost their way and are in need of reform.”

Legislative support

Windy Boy had been encouraged to run against Downing for the past few weeks before he announced plans to file Tuesday. He had been on the fence but then he saw an article by the Gazette last week on Downing and his run for reelection. The story noted the race has relatively few entrants, with the Downing touting his past wins in Congress.

“That was the straw that broke the camel's back for me, and his intention to proceed with the same agenda as you had in the past year,” Windy Boy said.

He said the tax cuts brought by the One Big Beautiful Bill will increase the federal debt, while Montanans will struggle with the non-renewal of marketplace health plan subsidies. A majority of 78,000 Montanans relied on subsidies to reduce the cost of their healthcare plan prior to 2026.

Meanwhile, the nonpartisan Congressional Budget Office projected the 2026 budget deficit as $100 billion larger than what was projected a year ago, with the tax cuts attached in the summer policy bill a significant part of that.

Next year, if he doesn’t succeed in the House race, Windy Boy is currently set to be the Senate dean, an informal title reserved for the longest-serving active legislator. Compared to the federal government, it’s a point of pride for him that he’s helped the state maintain a balanced budget during all that time.

State Sen. Ellie Boldman, D-Missoula, was one of a few legislators who had been pushing Windy Boy to run weeks ago. She and other legislators noted there was so much focus on the four-way Democratic primary challenging Rep. Ryan Zinke it seemed little was going on in the eastern district.

Democratic legislators, including Boldman, Bozeman Sen. Cora Neumann and Butte Sen. Derek Harvey thought Windy Boy might be the best option for the district.

In a statement to the Gazette, Boldman described Windy Boy as a lifelong Montanan, a respected tribal leader and a proven legislator that focuses on what matters to people within the state.

“And Jonathan, whether you're on the right or the left, you know that he's gonna follow his own heart,” she said in a subsequent interview. “He's not listening to any of those lobbyists, or necessarily a Republican or a Democrat.”

In 2018, Windy Boy was also the subject of a sexual harassment investigation for text messages he reportedly sent, telling the recipient they were “gorgeous” and a “sight for My Sore Eyes.” In another text message he reportedly told someone, “You can step all over me and there are no boundaries” in response to a female lawmaker wondering if she was overstepping boundaries in resolving an unrelated issue.

Legislative leadership confirmed at the time Windy Boy was the subject of the investigation and said he resigned as chair of the Tribal Relations committee before it could be stripped of him. However, the investigation prompted lawmakers to establish a new process for reporting and investigating sexual harassment.

"I've always pursued issues that positively impacted the people in my district and succeeded. Things come up in life and no crimes have been committed. My focus is to to move Montana issues forward to D.C.," Windy Boy stated in a text to the Gazette.

Relatively few Native Americans have been elected to Congress in U.S. history — around 20 — despite the millions of Indigenous people in the nation. Meanwhile, American Indians make up about 6.4% of Montana’s population, but about 8% of state legislature members are in the American Indian Caucus. The caucus’s share has mostly grown since Windy Boy started serving in the Legislature in 2003.

More than 20 years ago, Windy Boy ran out of frustration with current politicians too, challenging an incumbent. In 2001, he was chairman of the Montana Wyoming Tribal Leaders Council and went to Helena to testify on a bill that was shut down that same day. Expressing frustration after the hearing, he remembered being told by his representative that Windy Boy didn’t understand how things worked.

“And I told him straight up, ‘Well, I may not understand how things work here, but when you go for re-election next year, I'm going to take you off.’” Windy Boy said. “My reasoning for that is, if there's going to be any decisions on the people who I serve, then I want to be at the table making those decisions.”