Democrat Steve Bullock Won a Red State in 2016. Can He Beat Trump in 2020?

The governor of Montana thinks there’s still room for one more in the crowded Democratic primary field.

Steve Bullock, seen here campaigning in 2016, believes a red-state governor can beat Trump in 2020. (William Campbell / Corbis / Getty)

HELENA, Mont.—Yes, another Democrat running for president. Another white guy. Another politician most of the country has never heard of. Another candidate who doesn’t have a lot of money to start with, or any real hopes of meeting the low bar to make the stage for the first debates next month. Another dude whose last name begins with B who thinks that entering the 2020 race after 21 others makes perfect sense.

That’s Steve Bullock, the Democratic governor of Montana, who was elected to his second term in 2016 by four points on the same day Donald Trump won the state by 21 points. Bullock is not so subtly inching toward a presidential announcement expected for this week. On Friday afternoon, a Bullock aide and I rode in a slow-moving car while the likely 2020 candidate was literally running down the side of the highway as part of a charity race, a clip of which was then tweeted from his account with the caption “Feels like a good season to run.”

A few hours later, Bullock and I settled into a table at Jesters, a dive here a few blocks from the capitol building. “Hey, Steve!” the young bartender with the black baseball cap and the neck tattoos said. Supporters talk up how Bullock un-ironically wears cowboy boots. His natural affability was on display Friday afternoon at the bar. “Happy birthday, Sheila’s mom!” he said to a woman introduced to him by her daughter, who recognized his face. “Are you going to buy me a drink?” Sheila’s mom asked. He laughed. “I may have to!” Many others approached him during our conversation.

“Trump may have been right in diagnosing the frustration,” Bullock told me. “A whole lot of those folks were like, ‘All right, he’s somebody new. We’re going to drain the swamp.’ Don’t kid yourself: Their lives have not gotten better because of his actions and activities.”

Bullock currently sits at 0 percent in the few polls that have included him as an option, but 2020 is proving to be a race where even the expected heavyweights are struggling to break through. Bullock is poised to enter this week with a network of top advisers and the clear support of Iowa Attorney General Tom Miller, the longest serving Democrat currently elected statewide in the first caucus state. And he’s hoping to lean into a distinction that no one else in the field can claim.

“You look at this field, and there’s only one that’s won in a Trump state when Trump was on the ballot, or won statewide in a Trump state, period,” Bullock told me.

The competition skews so blue that Elizabeth Warren’s campaign was able to make a big deal in March that she’s the only candidate who has beaten an incumbent Republican—and that was in Massachusetts, for Teddy Kennedy’s old Senate seat. Of the Democrats running serious campaigns, Indiana’s Pete Buttigieg, Ohio’s Tim Ryan, and Texas’s Julían Castro and Beto O’Rourke are the ones who have been elected anywhere in a state Trump carried in 2016. To kick the president out of the White House, Democrats would need to flip at least three of the 30 states Trump claimed in 2016.

Like every other Democrat running, Bullock is pro–abortion rights and eager to tackle the human causes of climate change, and worries about Trump’s encouragement of hatred and lies. He can hold up the executive order he signed on net neutrality. He doesn’t support Medicare for All, but last week signed an expansion of Medicaid to provide coverage to 96,000 people in Montana. That doubled the number covered in the initial expansion Bullock signed back in 2015. The new law passed with eight Republicans in the state Senate and 20 Republicans in the state House; it joins laws signed in the past few months reducing pharmaceutical costs and reining in private-insurance-rate increases, which also passed with Republican support.

Bullock is not delusional. He understands that most political insiders think that a smart lawyer running on governing a Republican state with all of a million people might have been the perfect fit for, say, the 1992 presidential election, but not so much for where the Democratic Party seems like it’s headed in 2020. His emerging campaign is operating on such a shoestring budget that HQ staff is technically renting only half of a wide room in the former Blue Cross Blue Shield space in downtown Helena, not far from the city’s main drag, named Last Chance Gulch after 19th-century prospectors who found gold. It’s more than enough room, since four employees work out of the space right now. (Another eight, including a state director, spent the past weekend training in Iowa.) “It’s daunting,” Bullock acknowledged.

The 2020 field is full of legislators who have been part of Washington, and in the minority for most of their years there. To Bullock, that’s the essence of the problem. “Not doing a damn thing works for a lot of people. And it works really well for a lot of the interests that support the Republican Party. When government can’t work, [Republicans are] winning,” Bullock told me. “D.C. is now set up to have grand speeches, but not actually get anything done.”

Montana is a place where even the speaker of the statehouse lists his cell number on the government website. Before I flew out, it wasn’t hard to track down a few Republicans directly to see what they made of Bullock talking up his record on the new health-care laws, building up pre-K programs, and creating some of the nation’s tightest state-level restrictions on dark money, including rules that say all unofficial spending must end 90 days before an election. Bullock himself was a top target of the libertarian billionaire Koch brothers in 2016—more money was spent against him than any other candidate in Montana history.

Among the state’s GOP leadership, there’s frustration with the members who have worked with Bullock, common complaints of renegade “RINO” Republicans (Republicans in name only) who gave him his victories. State House Majority Leader Brad Tschida told me their behavior reminded him of an expression he heard used about some jocks back when he was a high-school administrator: “He looks like Tarzan, but plays like Jane.” On top of that, Tschida complains, it’s those Republicans who are taking the lead, not Bullock. “They create ideas for him rather than him saying, ‘Here’s what I want to get done,’” he says.

Tschida has more animosity toward Bullock than most other people, though his feelings of being sold out aren’t unique. “When [Bullock] says it’s a bipartisan way,” says Scott Sales, the president of the state Senate, “it isn’t like it’s the lion’s share of Republicans that have enabled him to claim that bipartisan way.” Then again, realistically, no Democrat would sign bills that a majority of Republicans support; Bullock’s boast isn’t that he’s cast a spell to convert everyone who disagrees with him, but that he has run the state and scored several progressive victories by getting enough Republicans in his corner. Of the other governors already in the presidential race, John Hickenlooper had some Republicans work with him on bills in Colorado, though he had Democratic control of one or both chambers of the legislature for his entire time in office, and Jay Inslee has been on a rapid run of progressive legislation in Washington in the past few months, since getting Democratic control of the state Senate.

“I’m not so naive to say, ‘Okay, we got this done in Montana—it’s going to be easy in Washington,’” Bullock told me. But he has a suggestion for how to start: new federal campaign-finance laws to fight the world that’s sprung up since the Supreme Court’s Citizens United decision, pushing members of Congress to put bills on the floor once they come through the committee process and not just at the whims of the leadership, and end the filibuster in the Senate to make more people answerable for their votes. All of that, of course, would be up to the Senate, which is a job that Bullock has forcefully rejected considering.

Indeed, a lot of Montana residents voted for both Bullock and Trump, but would any Trump voter actually pick Bullock over the incumbent president in 2020? Sales, who was about to take off for a trip down the Colorado River, told me he thought Trump would still win Montana, perhaps by 10 points. He’s not sure Bullock’s appeal will translate in other states, where he can’t meet as many voters, and where people aren’t as easily won over by a friendly presence. “Montana is like a 600-mile-long Main Street,” Sales says.

Montana is mostly white, mostly rural, mostly mountains. It’s a small enough state that a few weeks ago, a Boy Scout–troop leader reached out to Bullock online to ask the governor whether he could present a merit badge to a boy who’d missed a recent ceremony because he’d broken his leg, only to have his hamster die right before the make-up ceremony. Bullock showed up to do the deed.

“Even if we can cobble together 270 electoral votes, if you’re not winning back places that we’re not winning or competitive in, you’re not going to govern,” Bullock told me. The voters who feel that they’ve been left behind by the economy shouldn’t be supporting Trump, Bullock says, but it’s up to the Democrats to convince them of that. If “we’ve lost that voter, instead of saying, ‘We’ll actually give you a reason to vote for us,’ I think we’re missing something. And we’ll deserve to lose,” he says. He’s struggled to get national Democrats to agree with him.

“Initially, when I traveled and said 25 to 30 percent of my voters voted for Donald Trump, there was often a response of, ‘What’s wrong with those voters?’ or ‘What’s wrong with you?’” Bullock told me. “Never like, ‘How is it that we’re not sufficiently connecting with folks?’”

Bullock started thinking about running almost as far back as Election Night 2016. He was 50 years old, term-limited, and ambitious to do more, and had no interest in entering the Senate, no matter how many times Minority Leader Chuck Schumer tried to recruit him (many times).

He didn’t get serious about running for president until March, when he began staffing his PAC. He put off any campaign moves until after he finished his final legislative session. (The Montana state government meets for a few months every two years.) A planned teaser trip to New Hampshire a few months ago was scrapped because Bullock thought it would get in the way of Medicaid-expansion negotiations back home.

Realistically, Bullock’s run is all about Iowa, and it is the place he has so far invested in. An adviser told me Bullock will barely campaign elsewhere over the next 10 months—save for a few swings through New Hampshire, and perhaps the occasional stop in Nevada because it’s close enough to home. South Carolina is not on the table, nor is trying to mount the long-game operation some of the other campaigns have been building in anticipation of a drawn-out nomination process that could hinge on a rolling brawl for delegates all the way into next summer’s Democratic National Convention. This game plan seems out of sync with an election calendar that will include an intense month of coast-to-coast campaigning between the Iowa caucuses on February 3 and a Super Tuesday with more big primaries than ever before, on March 4.

Miller, the Iowa attorney general who’s been elected 10 times and is the godfather of Democratic politics in the state, says Bullock’s strategy is not crazy. He’s known Bullock for 10 years, and was already campaigning with him at the Iowa State Fair last summer. Miller told me he’s been getting calls from basically every other candidate, but refers to Bullock as “the package,” and says he’s confident Iowans will fall for the governor too. “With other candidates, they come to Iowa, they get a bump, and it fades,” Miller told me. “With Steve, because it’s all built on a strong foundation, it’ll continue to build, if it works.”

Bullock’s kitchen cabinet includes the Bill Clinton veteran Matt McKenna and Nick Baldick, who advised Al Gore in the 2000 election and served as John Edwards’s 2008 campaign manager. Jennifer Palmieri, Hillary Clinton’s 2016 communications director, is also serving as an informal adviser and sounding board. She knows most of the candidates in the field, has trained aides working on just about every other campaign, and wrote a best-selling book about political empowerment for women structured as a letter to the first female president. Currently six women are in the 2020 field, and Palmieri is one of the most prominent voices who have pushed back on those who say, “There’s just something about him I like,” because she thinks it’s the mirror image of the sexist “There’s just something about her I don’t like” that Clinton faced. Palmieri’s husband, Jim, used to talk up Bullock, and she says she used to roll her eyes, “skeptical that [Bullock] might be one of those red-state Democrats who wins by trashing the party. Obviously, he’s not.” She says Bullock feels “like a nice antidote to dark Trump times.”

Bullock and his team were relieved when Sherrod Brown decided not to run, since the Ohio senator would also have made the argument about being able to win in a Trump state. Joe Biden’s entry, meanwhile, didn’t change Bullock’s calculus. Bullock’s team likes the contrast—if Democrats are looking for a white guy making an electability argument, a Bullock adviser told me, he’d be there as one who’s younger and actually has a record of winning in Trump states.

“Montana, Montana, glory of the West,” croon the Helena Xpress Singers in four-part harmony inside the state capitol building. The dozen elder women wear matching blue, purple, magenta, and teal bedazzled shirts. “Of all the states from coast to coast, you’re easily the best.”

Upstairs in the old supreme-court chamber, Bullock hands out community-service awards. He delivers a line that he repeats often: “We have to act like our kids are watching. Because they are.” A conversation Bullock had with one of his teenage daughters was the catalyst for his 2016 campaign ad pushing for equal pay, against the advice of pollsters who told him it was the wrong way to go with Trump on the ballot. (His daughter narrated the spot.) Bullock is protective of his kids, and when I ask him what he tells them about a president and presidency that he thinks violates preschool lessons about how to behave, he freezes up, saying he’s reluctant to bring private parenting conversations into a political conversation.

Bullock’s relationship with his own father was more complicated, in a way that the governor’s friends told me might explain why Bullock is always hyperaware of what’s happening in a room, always checking in with people, asking about their lives. His parents divorced when he was in grade school, and 20 years later—after Bullock left for a job at a law firm in Washington following a failed first run for Montana attorney general—he moved back home to help care for his father, who was dying of cancer. Bullock says he never includes the words “I’m proud of” in speeches, because that makes it about him and not whomever he’s speaking about. I ask whether he thinks his father would be proud of him. He pauses for a beat.

“He would be proud that you walk through this place, and there’s folks I’ve never met that felt comfortable enough to say, ‘Thank you for what you do,’” Bullock told me. I ask whether his father would be surprised to see his son thinking about running for president. “Yeah,” Bullock says, though he points out that his father died 15 years ago. “In 2004, I’d be surprised that I was thinking about a presidential run.” When I ask how he’s going to understand or connect with a country that is so different from Montana, he speaks broadly about fatherhood: “The challenges might be different, but a parent still wants the same thing for their kids.”

Bullock has clearly practiced that answer, along with others. When asked about running as a long-shot candidate, he says that at the very least, maybe he’ll shape the debate. When pressed about entering the race as another white guy, he highlights his record, including an executive order tackling LGBTQ discrimination that the Human Rights Campaign cites as a model for others. He also says he often thinks about statistics such as the disproportionate rate of African American women dying in childbirth.

“When I’d get into ‘the white guy from Montana’ [conversation], I’d approach it that I’d show up, I’d listen more than I’d talk, and also understand that there are historical, systemic, and contemporary barriers we have to address,” Bullock says.

It’s safe to say we were the only people at Jesters talking about executive orders and white privilege—though the bar features gender-neutral bathrooms with We Don’t Care written on the doors.

“Finally, someone who agrees with me on shit,” another woman at Jesters told him, right before we headed for a table at the start of our conversation. “And in a Republican state.”

She handed Bullock a little plastic figurine of a man to balance on the rim of his glass. He adjusted it and thanked her. Bullock needs more voters like this woman—somewhere between 50,000 and 70,000 Iowans—to have a shot at this thing. And then, like, 65 million more people around the country.