This July, Jonathan Kreiss-Tomkins spent four days and 450 miles (725km) wending his way down the Yukon River in a 24-ft Alweld skiff, a flat-bottomed aluminum boat built for shallow Alaska rivers.

Starting in Koyukon Athabascan country, he passed through Indigenous Deg Hit’an communities like Anvik, before ending among the Yup’ik villages of the lower river, Russian Mission and Pilot Station among them. The boat carried him through 11 villages – some only reachable by water or small plane, and most with fewer than 300 residents, and fewer still who could recall the last time they had seen a candidate for Alaska governor, Republican, Democrat or independent.

The 37-year-old former state representative is hopping on snowmachines – only people in the lower 48 call them snowmobiles – as well as boats and floatplanes to accomplish what Alaska Democrats have failed to do for nearly a generation: win the governor’s office.

“Alaskans are hungry for change,” Kreiss-Tomkins said. “We’ve been running the same campaign since we launched in February, and I don’t take anyone’s vote for granted.”

Just two years after Donald Trump carried Alaska by 13 points, his approval rating there has collapsed – a net 21- to 22-point swing, among the steepest drops in any reliably Republican state he won.

In August, Kreiss-Tomkins came in first ahead of his Democratic and Republican rivals in the state’s nonpartisan primary. Now, “JKT”, as he’s known in his home town of Sitka, is betting that an old-fashioned exercise in retail politics – traveling the vast expanse of a state larger than Texas, California and Montana combined and asking voters for their support in person – will help him do it again in November.

But a question looms over the race: how much of his strength is a reflection of the changing national political environment, and Americans’ broad dissatisfaction with Trump, and how much is particular to the candidates, personalities and particular electoral system of the last frontier?

Unlike nearly every other US state, Alaska no longer holds a traditional party primary followed by a winner-take-all general election. Under the ranked-choice voting system adopted by voters in 2020, the top four candidates from an open primary advance to the general election. Voters then rank candidates in order of preference, and votes can transfer to their next-ranked candidate as lower-placed contenders are eliminated.

Though reliably Republican, the state has a long independent streak. The outgoing governor, Mike Dunleavy, an early supporter of Trump, leaves office deeply unpopular, largely for his unfulfilled promise to increase the amount of oil-dividend money Alaskans are given each year; in 2026, every eligible Alaskan received $1,000, with an additional $200 energy relief payment.

This localized frustration coupled with Trump’s sagging approval ratings, particularly on the economy, has created a potential opening for Democrats. A recent bipartisan AARP poll found Kreiss-Tomkins winning 40% of first-choice preferences, compared with a combined 41% for his three Republican opponents, Bernadette Wilson, Dave Bronson and Treg Taylor, all of whom will appear on Alaska’s general election ballot.

Kreiss-Tomkins grew up in Sitka, a fishing town of 8,500 where compromise is required. It’s wedged among the spruce and hemlock of the Tongass national forest and the open swell of the north Pacific, where you can’t escape political opponents in a town with just 14 miles of coastal road, accessible only by water or air. He entered politics in 2012, at the age of 22, winning a statehouse seat by defeating the Republican incumbent by 32 votes.

“JKT is the clear frontrunner for governor not because of anything Trump did, but because he’s running a good campaign,” said Larry Persily, who has watched Alaska politics since the 1970s, first as the owner of the Wrangell Sentinel newspaper and later as an editorial page editor at the Anchorage Daily News. “He’s energized a lot of young people. His Republican opponents are just a sorry lot. The Republicans just put up a bunch of political losers.”

Wilson, the top-finishing Republican candidate, would disagree.

The Anchorage garbage-hauling entrepreneur, who finished third in August’s primary, is a former competitive figure skater and the great-niece of the late Republican governor Wally Hickel. She has secured endorsements from the Arkansas governor, Sarah Huckabee Sanders, one of Trump’s press secretaries during his first term, and Alaska’s own Republican congressman, Nick Begich – along with Byron Donalds, the Florida congressman running to succeed Ron DeSantis as governor there.

Wilson casts Kreiss-Tomkins’s decade in elected office, and his elite educational background – he dropped out of Yale University in 2011, one credit short of graduating – as liabilities.

“Alaskans are looking for fresh leadership from the private sector,” she said in an emailed statement. “Not another ‘experienced’ politician who will wreck our energy economy, raise taxes, continue to fail us on the PFD [permanent fund dividend], and sell out Alaska to advance their career.”

Wilson’s relationship with one of her Republican rivals is tangled: she chaired Bronson’s 2020 campaign for Anchorage mayor. He won, arrived in office as a political newcomer, then spent his single term fighting the assembly over homelessness – at one point floating one-way plane tickets to the lower 48 for people living on the street – before losing re-election to the independent Suzanne LaFrance in 2024.

Republican candidate Taylor’s route to the ballot has been stranger still. The former state attorney general was elevated to the final slot after Tom Begich withdrew and endorsed Kreiss-Tomkins, only to be disqualified four days later over an undeclared rental income disclosure; briefly replaced by his own running mate; then reinstated after a department of law review – conducted by the office he used to run – found trivial but, he claimed, similar issues among dozens of other candidates.

The three Republicans’ competing campaigns have prompted efforts to consolidate conservative support behind Wilson. Alaska’s electoral history offers a precedent. In 1994, Democrat Tony Knowles won the governorship by just 536 votes after the conservative vote split between Republican nominee Jim Campbell and Jack Coghill, the sitting lieutenant governor, who ran on the Alaskan independence party ticket. Knowles, the last Democrat elected to the office, went on to serve two terms.

The governor’s race is unfolding against a national backdrop of declining approval for Trump. A Reuters/Ipsos poll published in September put his approval at 32%, with dissatisfaction over living costs among the principal concerns. But national figures alone cannot explain what is happening in Alaska, where the statewide candidates are also confronting distinctly local issues.

Electing a Democrat here is not as surprising as it is in some other red states, said Tom Kizzia, a longtime Anchorage Daily News reporter and Alaska historian. “It’s that Alaska iconoclasm that kicks in – the simmering resentment of big business ripping off our resources.”

The common thread, in Kizzia’s telling, is not a particular political party, but rather a distrust of whoever is currently perceived as extracting Alaska’s wealth without giving enough back – a role historically filled by outside oil and mining interests, and one conservatives have often redirected toward the federal government instead.

That history helps explain why Trump’s brand of politics has not translated into durable support for his allies on this year’s ballot. “Dunleavy hitched himself to the Maga wagon, which contained elements of that iconoclasm,” Kizzia says. “But Trump was mostly about non-Alaska things that don’t register strongly with Alaska voters.”

What does register, he argues, is Dunleavy’s failure to deliver on a hefty permanent fund check, the annual payment that Alaskans receive from the state’s oil-wealth savings each October. Dunleavy promised to up the amount of these checks, and even to pay Alaskans retroactively. None of this has come to pass. This same unresolved grievance now faces all three Republicans running to succeed him.

Kreiss-Tomkins argues for a dividend payment that can be maintained without destabilizing the budget.

“I want a permanent fund dividend that is meaningful and sustainable. We don’t need an election-year promise that blows a hole in the budget and is mathematically impossible,” he said.

His campaign blends the Alaska tradition of “visiting” with people, sometimes aboard his skiff retrofitted with a three-quarter-ply cabin with the amber varnish flaking off, with a volunteer operation nicknamed “Superpod”, built on the premise that someone responding to a campaign text should reach an actual human being rather than a bot.

That emphasis on personal contact was apparent to Debbie Moderow, who operates sled dog kennels near Denali national park and in Anchorage. At a meet-and-greet in Anchorage attended by about 30 people, she watched Kreiss-Tomkins climb onto a folding chair to address the crowd. “He was brimming with energy and wisdom, young and bright-eyed, and it was obvious that he had been obsessed with government in a geeky way for a long time,” she said. “I immediately thought, this guy has a vision, and a way to chart the way forward at a time when our state desperately needs it.”

Persily, the newspaper publisher, who keeps his 100-year-old Underwood manual typewriter atop a restored lead-type cabinet, and pops in CDs for music, sees the campaign’s emphasis on face-to-face campaigning as significant.

“Elections are determined by turnout,” he said. “If you can turn out people who wouldn’t otherwise vote, that will make the difference. The public in the state is looking for someone who is going to excite people who wouldn’t otherwise get engaged. On a boat, on a snowmachine, what have you – Jonathan Kreiss-Tomkins, from what I can see, is making that happen.”

It hasn’t been without hiccups. Kreiss-Tomkins’s campaign has attracted criticism over its finances. He outraised the entire field during the primary, drawing substantial contributions from outside Alaska, including six-figure sums from employees of artificial intelligence companies.

He has responded by emphasizing his proposed moratorium on new Alaska datacenters and his support for regulations intended to protect Alaskans from harms associated with AI. His position is that the donations reflect support for his proposals rather than an effort to influence them.

Asked about his priorities in office, Kreiss-Tomkins returns to two concerns familiar to Alaskans: education and the cost of living.

“Our top-of-mind campaign issues are supporting our schools and lowering everyday costs for Alaskans,” he said.

Whether dissatisfaction with Trump translates into votes for Democratic candidates remains a separate question from whether Kreiss-Tomkins can assemble a coalition of his own. The governor’s race will test both possibilities, alongside the ability of Alaska’s ranked-choice system to accommodate three Republican candidates competing for many of the same voters.

For Moderow, Kreiss-Tomkins’s relative youth is less significant than his years of experience in Juneau. “People frame it as giving a young guy a chance,” she said. “For me, it’s the opposite. It’s giving a professional an opportunity when Alaska needs a leader.”