This story was originally published in April. It has been updated. Montana's special election for the open US House seat is Thursday.

Hamilton, Montana (CNN) Rob Quist, a 69-year-old singer songwriter-turned-Democratic congressional candidate, recently delivered his stump speech on a trailer stage in a backyard in rural Ravalli County to a crowd that is a bit bigger than what one might expect in a place that voted by nearly 40 points in November to elect President Donald Trump.

"It's like the sleeping giant has awoken," Quist said looking into the audience. "It's truly amazing."

Quist waits for a campaign aide to fetch his guitar so he can perform his self-composed campaign song. In classic Quist form, he told a story you wouldn't expect from a politician about skinny dipping.

"The rule is, you know, I always try to jump into the water someplace in Western Montana before the first of June," he said. "We were hiking up one of these creeks up here and I realized it was the last day of May so I shucked off all my clothes. You can't dabble your toe in because if you do, you chicken out. So in I went and all of a sudden it was like my whole body contorted. I thought I was going to have a heart attack right there. It was definitely a baptism."

His audience roared in laughter.

This is Trump country through and through, but on a 45-degree Sunday evening in April, more than 100 supporters are standing around bonfires, hopeful that Quist could win the special election to replace Interior Secretary Ryan Zinke and send a warning shot to Washington that Democrats -- even in rural Republican strongholds where they haven't won a House seat in two decades -- are mobilized against the President.

"I have always had opinions, but until this Trump election, I've never done anything," said Joni Lubke, a 39-year-old Hamilton resident. "The Trump situation really fired me up because I can't stand the hatred that's been coming out from it. I just want to speak up for those people who don't have voices. ... Quist just feels like he's one of us."

Kierstin Schmitt, a 47-year-old from just outside Hamilton said her involvement in the Quist campaign has a lot to do with the fact Trump won too.

"It was a big reminder that the reason why he won was partially because we were a bit complacent with (President Barack) Obama in office and thought someone had our interests in mind," she said. "That's not the case anymore."

In the wake of a Kansas special election where the Democrat outperformed expectations and another special in Georgia where a Democrat is competitive, there are real opportunities for Democrats in Montana.

Democrats are hopeful that the populist streak that catapulted Trump to the White House in November and elevated independent Bernie Sanders in the Democratic primary may boost their unorthodox candidate, a banjo player and former member of the Montana-famous Mission Mountain Wood Band who is prone to quoting Hemingway, wearing the same shirt two days in a row on the campaign trail and reciting his own poetry on the stump.

Quist, who looks like he rode straight out of a 1970s-era Western, has a thick black mustache, white cowboy hat and silk handkerchief hanging from his neck. He's making a play for communities like Hamilton, places he says aren't that unlike the town of Cut Bank, where he grew up on the highline, a rural corner of the state that isn't always frequented by Democratic politicians.

Donald Trump Jr., Mike Pence campaign

Quist is facing a formidable opponent: Bozeman-based Republican Greg Gianforte, a tech entrepreneur and multi-millionaire who sold his self-made company RightNow Technologies to Oracle in 2012.

"He's got a track record of getting things done and problem-solving," said Patrick Johnson, a Helena resident who came to see Gianforte speak.

"Anything can happen, but boy, we got a good candidate," said Bridget Johnson, a 75-year-old Helena resident and another Gianforte supporter.

Gianforte has deep pockets and high name recognition after mounting an unsuccessful gubernatorial campaign in 2016. He's estimated to have spent more than $5.1 million of his own money on the governor's race and has outraised Quist $1.6 million to just shy of $1 million in the first quarter, which ended March 31.

Gianforte also got a boost from the National Republican Congressional Committee's campaign arm and Donald Trump's son, Donald Trump Jr., campaigned for Gianforte throughout the state the following week. Vice President Mike Pence also recently campaigned for Gianforte during a two-day swing.

Making matters even tougher for Quist is that the special election is on a Thursday in May just before Memorial Day weekend, a factor that some worry could cripple Democratic turnout.

Still, Montanans are known to have an independent streak. Trump won the state by more than 20 points in November and on the same night, Montanans re-elected Gov. Steve Bullock, a Democrat.

Hunting trophies and public lands

At his home in Bozeman -- the same one where Gianforte started RightNow Technologies decades ago with just $5,000 -- Gianforte points out the floor to ceiling collection of framed family photos he keeps of backcountry camping trips and hunting expeditions. In a game room, he proudly exhibits the hunting trophies he's shot over the years. An elevated white mountain goat greets visitors in the entryway along with a standing black bear Gianforte shot with his own bow and arrow.

Democrats have tried to cast Gianforte -- a 24-year Montana resident -- as a disconnected New Jersey outsider, a dangerous label in a state where residents prize deep roots above all else.

"We made the decision to start the business here," Gianforte said. "We made the decision to raise our family here."

Rob Quist, the Democratic candidate running for Congress in Montana meets with voters at a brewery in Phillipsburg.

But even some Republican voters are skeptical of Gianforte's wealth and willingness to run for governor in 2016, fail and then turn around and run for the open congressional job so soon.

"I like the guy with the cowboy hat, but he's a Democrat," said lifelong Republican voter Bob Hackel, a 35-year resident of Hamilton. "I don't like the millionaire because he's just wishy washy. He wants either to be governor or he wants to be this or wants to be that. He doesn't know what he wants. He just wants something."

Linda Vaughey, a Helena resident and Gianforte supporter, said that Republicans need to celebrate Gianforte's success not ridicule his ambition.

"His strengths are in his background, his ability to problem solve," Vaughey said. "He started out with nothing and so in this very complicated, complex world we're living in who would you rather have someone who doesn't know how to get ahead?"

Attacks against Gianforte have also included charges his family's foundation donated exhibits to a creationist dinosaur museum in Glendive that bills itself as the "the largest dinosaur and fossil museum in the context of biblical history."

When asked about his donation, Gianforte said his foundation donates to all kinds of causes, but in this case "there was an opportunity to do an economic development project in Glendive. And we supported it."

'A fight for the soul of Montana'

Democrats also argue that Gianforte is an enemy of public lands. It was a common refrain in the governor's race that Gianforte tried to block access to public lands after the Republican filed a lawsuit in 2009 over an easement boundary on a river near his house.

It's "a fight for the soul of Montana," Quist often tells voters on the stump.

Gianforte argues the lawsuit was little more than a misunderstanding in which he -- like a lot of Americans -- had a disagreement with a government agency. Gianforte said he filed the lawsuit against Montana Fish and Wildlife after spending 18 months writing letters and calling the agency to come out to the property to resolve a surveying issue.

"This is standard rhetoric from the left," Gianforte told CNN in an interview. "Let me be really clear. Public lands need to stay in public hands. Period."

If the Democratic playbook is to cast Gianforte as an outsider, the Republican one is to paint Quist as a foot soldier of Democratic leaders in Washington. An early GOP ad against Quist charged he was "out of tune" with Montana values.

On the campaign trail in Montana, Gianforte tells voters his opponent supports a gun registry as well as sanctuary cities.

"That's not a Montana value," Gianforte said at an event in Helena.

"My opponent has said we should have 100% government-run health care. You want to see what that looks like, all you have to do is look at the VA," Gianforte said.

"Democratic voters have shown that they are certainly energized in a lot of these special elections, but as it pertains to Montana you have a strong candidate in Greg Gianforte who has a strong message that appeals to a broad swath of Montana voters contrasted with a liberal musician with a dubious financial past," said Jesse Hunt, the national press secretary for the NRCC.

Quist responded to the gun control charge by calling it a "false attack."

"Greg Gianforte is putting out false attacks because he knows we have the momentum," Quist said in a statement. "I come from a ranching and farming household and I have guns older than the number of years Greg Gianforte has been in Montana. I am a stronger supporter of our Second Amendment rights."

A race about health care

Across the state, Quist talks a lot about health care. It's a major contrast from the strategy deployed by other rural, red-state Democrats who have traditionally shied away from Obamacare politics on the campaign trail.

But in the wake of Republicans' initial failure to repeal the law and polls showing record popularity for the Affordable Care Act, Quist has made Obamacare a centerpiece of his campaign, holding health care town halls, visiting American Indian health care centers and sharing his own story about how a bungled operation left him financially strapped. The House eventually passed a bill repealing and replacing Obamacare weeks later, but the Senate has yet to take up that proposal or unveil their own.

Quist has blamed a 16-year debt history that included unpaid property taxes and other bills reported on by the Billings Gazette and The Associated Press earlier this year, on health problems.

When asked about his long-history of financial problems, Quist argues it is just further proof that Americans need better access to affordable health care.

Greg Gianforte, the Republican candidate for Congress shows some old family photos of camping in the backcountry in his home in Bozeman.

"Even here tonight, people came up and said 'you know, I've had the same kind of issues that you've had, and finally we have someone who has kind of gone through that and can be a voice for us.' My opponent has no idea what people like this go through," Quist said.

Republicans say it shows Quist has a double standard for himself versus regular taxpayers.

"It raises a question of personal responsibility," said Montana Republican Party Executive Director Tim Gould. "Montanans don't want a Congressman who wants to raise their taxes but won't pay his own."

Voters across the state who spoke to CNN largely dismissed any presumption that Quist's financial history made him less qualified.

"You know he's going to be attacked by all this out of state, rich people's money and I hope it backfires on them because he just doesn't have the money. I mean literally, this guy has gone through a lot of financial hardships like a lot of people so they're using that against him," said Scott Thompson, a Democratic voter from Whitefish. "A billionaire is using the fact Rob Quist has had financial hardships against him. That's not compelling."

But Gianforte has also avoided fully embracing the Republican Party's plan to repeal Obamacare.

"I don't think we were there yet," the GOP candidate said of the House leadership's health care bill. "Obamacare is not working. It's in a death spiral. We need to repeal it and we need to replace it, but that replacement must bring premiums down and it must preserve rural access.

"This is just one guy's assessment, but I think there was a lot of work to try and get that plan pushed through on the seventh-year anniversary of Obamacare for some, and it was just a little too cute," he added. "That cake needed to stay in the oven for a little longer."