The Alaskan Who Could Lead Progressives Out of the Wilderness

The Alaskan Who Could Lead Progressives Out of the Wilderness

By Nick Fouriezos

Jonathan Kreiss-Tomkins is a 28-year-old legislator orchestrating a progressive surge from his home on a no-internet, no-cell-service island.
SourceNick Fouriezos/OZY


Because he has plans — and Democratic leaders are listening.

By Nick Fouriezos

Welcome to The Wilderness, an OZY original series charting how Democrats are trying to climb out of their historic hole. Read more.

Jonathan Kreiss-Tomkins is known to run marathons up mountain trails for fun. He once climbed Argentina’s Ojos del Salado, the tallest volcano in the world, to definitively prove it was higher than a neighboring Chilean peak. He was a skilled cellist, a regional champion debator and an online organizer for a U.S. presidential campaign, all before graduating high school.  

In a mythic land known for its larger-than-life characters, this 28-year-old is already one of the most interesting men in Alaska. And when all is said and done, he could wind up one of its most consequential.

Not that you’d know it meeting the soft-spoken state representative in his hometown of Sitka, a former Russian settlement accessible only by plane or boat. Clad in running shorts and a United Fishermen of Alaska cap, the youngest member of the Alaskan legislature somehow seems even younger as he chats up a crusty, bearded fisherman in the Back Door Café. He asks questions as often as he answers them, listening intently, his skinny arms tucked into the pockets of his teal windbreaker. It boggles the mind that almost six years ago, as a Yale senior one credit shy of graduation, he quit school to challenge the incumbent Republican co-chair of Alaska’s powerful state finance committee — and won by 32 votes.

Since pulling that upset, Kreiss-Tomkins has put remote Sitka on the national radar. The Nation called him “Alaska’s Lesson for the Left,” and he was named to the Washington Post’s “40 under 40” in 2014. More tangibly, he led the passage of a bill that made 20 Native dialects official languages of Alaska, a win for his indigenous-heavy district and no small task coming from a legislator stuck in what was then the minority party. Despite his youth, Kreiss-Tomkins has emerged as one of the strategic players keying a resurgence for liberals in Alaska — a turnaround that culminated with a November takeover of the Alaska House by a Democrat-led coalition of liberals, independents and moderate conservatives.

How can the lower 48 left replicate progressive successes in Alaska? The answer is complicated.

It’s true that party leaders brokered the final deal restoring Democrats to power in the state capital, the nation’s only blue legislative chamber in a Trump-backing state. But that shift would not have been possible without Kreiss-Tomkins — the person to identify, and convince to run, the two elected independents who eventually formed the backbone of the coalition. He also played a role in persuading the three moderate Republicans who joined in the compromise, says Democrat Bruce Botelho, the former Alaska attorney general and mayor of Juneau: “He is a pollinator. His mind is constantly engaged in trying to figure out connections.” 

What’s more, Kreiss-Tomkins is only getting started, speaking weekly with influential Democrats, including former DNC chair Howard Dean, about solving this not-so-simple question: How can the lower 48 left replicate progressive successes in Alaska? The answer is complicated, but the diminutive lawmaker is charting a path forward — one that, if successful, could bring the eyes of the nation to this remote island chain in the Last Frontier. “It’s absolutely replicable,” says Dean, who is working with Hillary Clinton’s new political group Onward Together to champion liberal candidates and causes. “Jonathan actually is a model for what we’re trying to do.”


Kreiss-Tomkins is packed into his Sitka office, cluttered with trinkets, including a 64-ounce growler from Baranof Island Brewing Company (filled with water) and a pop-up White House card auto-signed by the Obamas. One feature stands out: Tacked to the wall are printouts of Excel broadsheets showing his predictions for the winner of every governor and U.S. Senate election. The year? It was 2002, when Kreiss-Tomkins was in middle school. 

His projections were only 80 percent correct, but the exercise reflects the near-obsessive quality that threads through his life. As a 6-year-old, Kreiss-Tomkins says he memorized the population of every American city with more than 20,000 residents, poring over the census data in his parents’ Rand McNally atlas (his dad, an occasional commercial fisherman, his mom, a Yale-trained doctor with the Indian Health Service). Later, online chess and fantasy baseball fed his fervor and, the summer between seventh and eighth grades, Kreiss-Tomkins stumbled on an online progressive message board called Democratic Underground. 

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Alaskan Rep. Jonathan Kreiss-Tomkins meets with constituents on a retrofitted helicopter barge.

Source Nick Fouriezos/OZY

There, Kreiss-Tomkins began forming his political philosophy. After memorizing the names of all 100 U.S. Senators, 50 state governors and attorneys general and hundreds of members of Congress, he set to figuring out who could be the next president. Using an online questionnaire he created, he quizzed people from every state, digging into the political demographics of the nation. His research told him that the Iraq War was going to tank in popularity, and a socially progressive, fiscally moderate governor could beat George W. Bush in the 2004 presidential election. 

So, in December of 2002, Kreiss-Tomkins threw all his (adolescent) weight behind the Democrat he thought was most electable: Howard Dean. He reached out and then visited Burlington, Vermont, the next year, around the time Al Gore endorsed Dean for president. “I was like, ‘Holy shit,’ ” Dean remembers, both impressed and concerned about having a teenager on the campaign trail. “We had tons of young people coming from all over the country living in crash houses and rented apartments — not appropriate for a 14-year-old.” 


Despite Dean’s loss, the experience proved instructive when Kreiss-Tomkins, by then a Yale political science major, had to decide whether to wage a campaign of his own. In 2012, eight-year incumbent Bill Thomas was well-moneyed, and no Democrat had stepped up to challenge him. One week before the filing deadline, a state party member and Gershon Cohen, a clean-water activist who had met the high school debater years earlier, approached Kreiss-Tomkins about a run. “He was bright, articulate,” Cohen says, and it was clear the kid was passionate about politics. In part due to recent redistricting, Kreiss-Tomkins saw a path for victory where few did. After studying Thomas’ positions, he took the chance. 

Kreiss-Tomkins never did graduate. But after knocking on thousands of doors, calling out his opponent for supporting a tax break for big oil companies and canvassing his archipelago district in a float plane, he squeaked out his surprising victory.


Today, Kreiss-Tomkins stands aboard a retrofitted helicopter landing barge, listening to two constituents talk about converting the vessel into a mobile, floating seafood processor. He believes the process could revolutionize Alaska’s fishing industry by shifting power from foreign mega-corporations to mom-and-pop vessels. The day before, he was huddled over a computer screen, working with staffers on a proposal to convert 800 miles of service road along the Trans-Alaska Pipeline into a “recreation corridor” — hiking, cross-country skiing, dog mushing, fatbiking — to attract money to the state’s second biggest industry, tourism, amid a budget crisis caused by plunging oil prices.

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Kreiss-Tomkins takes a call while boating to his home on Big Marshall Island in Sitka. 

Source Nick Fouriezos/OZY

To some of his critics, Kreiss-Tomkins has yet to bring home the bacon. The pipeline trail wouldn’t be based in Sitka, for one. And the man who calls his ideology “socially progressive, fiscally moderate, politically pragmatic” hasn’t broken through partisanship to pass legislation, except for the Native Languages bill. That’s made him “no innocent bystander” to the legislature’s dysfunction, as Republican Sheila Finkenbinder said while opposing him last election, and she stands by her criticism today.

Kreiss-Tomkins responds by saying “those first four years, it was much more about stopping bad things,” such as an education reform that would have closed 10 schools in his district. Most of his projects — from fellowships drawing more than 100 interns to Sitka to plans for an entirely student-run college in his district — seem aimed at bringing the world to his tiny hometown. And while his early efforts are modest, Kreiss-Tomkins is currently engaged in a task that could launch him and his backyard to national prominence: creating the path for a progressive resurgence in America. 

It’s a tall task even for this mountain climber, and Kreiss-Tomkins is more likely to fail than not. Nationally, Republicans control two-thirds of state legislatures and 34 governorships — tying their all-time high from 1922. What’s more, there are 25 Democratic-controlled U.S. Senate seats up for grabs next year, including 10 in states Trump won. While national winds appear to be blowing in Democrats’ direction in 2018, they failed to convert anti-Trump energy to victories in five closely watched special congressional elections this year.

This Alaskan believes it starts with drafting talented candidates, which sounds obvious, but sometimes that means backing non-Democrats — as Kreiss-Tomkins did when helping independents Dan Ortiz and Jason Grenn seize previously Republican seats. Blue State Digital CEO Joe Rospars, the former new media director for both of Barack Obama’s presidential campaigns, agrees: “My suspicion is you’re going to see this wave of people running for office who look like those textbook civic leaders,” rather than strict partisans. In Alaska, Kreiss-Tomkins already sees lawmakers working with people who, elsewhere, would be “separated like cats and dogs, Montagues and Capulets.” 

Like Dean’s 50-state strategy, the goal is to target areas typically forgotten and overlooked. But Kreiss-Tomkins takes it one step forward: Candidates should reflect the values of their voters — even if it makes Washington Democrats uncomfortable (see the recent debate over whether the party should back anti-abortion candidates). Small states are key, he insists, where just a few voices can make an outsize difference. Adds Dean: “It’s a lot easier of a political environment, because people first look at you as a person, and only later as some category.” The strategy has to change with the demographics, Kreiss-Tomkins believes: “It makes sense to work with people in the moral foundations they have.” That’s the Cliff’s Notes version of the strategy that, to this point, Kreiss-Tomkins has circulated in Democratic circles but otherwise has kept close to his chest. 

As Kreiss-Tomkins waits to see whether his national playbook gains traction, his days mostly end like this one: Revving the 50-horsepower motor on his aluminum skiff, Kreiss-Tomkins bears south to the island, where he lives alone. If he has his way, this two-room rented shack with no internet or cell service will be an unlikely way station on the Democratic Party’s path back to power.