Still searching for their first major electoral victory against President Trump, Democrats are pinning their hopes on a cowboy poet to channel the energy of the grass roots into winning a Montana seat that Republicans have held for two decades.

After losing a Kansas race, being forced into a runoff in Georgia and all but ignoring a South Carolina special election, Democrats need a marquee win somewhere to show that anti-Trump anger can translate into votes at the ballot box.

Enter Rob Quist, a 69-year-old guitar-toting political newcomer who is the Democratic nominee for the May 25 showdown with Republican Greg Gianforte for Montana’s lone U.S. House seat.

“Montana’s special, maybe offers a little bit of an opportunity for [Democrats], because it is not as red as the Kansas 4th Congressional District. But nonetheless, Donald Trump won Montana by over 20 points,” said Geoffrey Skelley, of the University of Virginia Center for Politics.

Four Republican-held seats in the U.S. House opened up this year after their occupants took jobs in the Trump administration. Each of them was in fairly “red” territory, but Democrats predicted that an anti-Trump surge would energize their base and give them chances to fill those vacancies.

However, a Republican has already won the Kansas election and is expected to win the South Carolina race, leaving the Montana and Georgia contests as Democrats’ best bets.

Republicans are not taking anything for granted.

Donald Trump Jr., the president’s son, campaigned with Mr. Gianforte on Thursday for the second time in a less than a month. Vice President Mike Pence is slated to campaign on Friday with the Republican businessman, who lost his bid for governor last year.

The Congressional Leadership Fund, a political action committee dedicated to defending House Republicans, has emptied $2 million into the race, funding attack ads casting Mr. Quist as “more Nancy Pelosi than Montana.” The National Republican Campaign Committee rolled out a television ad Thursday raising questions about the singer-songwriter’s financial history.

“Rob Quist hired us to build a dance floor at his house,” a man named Kraig says in the ad. “After we completed the job, he stiffed us.”

Tina Olechowski, a Quist spokeswoman, said the attacks show that the Democrat is gaining ground in the race.

“The momentum is behind Rob Quist, with Montanans across the state supporting Rob as an independent voice who will protect Montana’s public lands, fight for affordable health care and support tax cuts for small businesses and working families, not millionaires,” Ms. Olechowski said.

The Democratic Congressional Campaign Committee has invested $600,000 into pro-Quist television ad buys and get-out-the-vote efforts, and populist Sen. Bernard Sanders of Vermont is slated to campaign with the Democrat this month.

Tightening polls

A Gravis poll shows that Mr. Quist has cut Mr. Gianforte’s lead to 8 percentage points in a district that Republican Rep. Ryan Zinke won by 15 points in November. Mr. Zinke stepped down to become Mr. Trump’s interior secretary.

“Our grass-roots momentum is unstoppable,” the Quist campaign said in one of a series of fundraising emails this week. “That’s why D.C. Republicans are scrambling to stop us — they’re terrified that we’re going to win this seat. So folks, let’s deal them a defeat that they won’t forget.”

Mr. Sanders and other liberal activists are hoping national Democratic power brokers don’t shortchange the race. They criticized the party for not putting more effort into the Kansas race last month, when Democrat James Thompson came within 7 percentage points of defeating Republican Ron Estes. Mr. Trump carried the district by 27 points in November.

Mr. Skelley said Georgia, where Democrat Jon Ossoff narrowly missed winning the race outright last month, is still the party’s best shot but that their battles are all uphill. Democrats now are struggling to find a balance between keeping activists bullish while tempering expectations.

“Most of the special elections are taking place in districts that Democrats would need absolutely everything and then some to go their way to actually win,” Mr. Skelley said.

The special election in Montana will be the first since the House narrowly voted last week to repeal and replace Obamacare, which has added to the liberal outrage against Mr. Trump and his Republican allies on Capitol Hill.

The New York Times reported last week that Mr. Gianforte has sent mixed messages about the health care bill, telling donors in a private phone call that he was “thankful for” its approval in the House, while his aides said he would not have voted for the bill because he did not know what was in it.

Tom Perez, chairman of the Democratic National Committee, blasted out a fundraising email this week reminding voters that the last time Democrats held Montana’s lone seat in the House was 20 years ago.

“But in a couple of weeks, we have a chance to flip that seat from red to blue and elect someone who will represent Montana values in Congress — standing up for working people, protecting affordable health care and Medicare, and demanding equality and fair treatment for all,” Mr. Perez said.

Christy Setzer, a Democratic strategist, said both parties could walk away from the special election season with bragging rights.

“In this case, everyone has reason for optimism: Republicans can take heart that Democrats haven’t yet outright won a new seat; Democrats can feel good about overperforming by double digits in deep-red states,” Ms. Setzer said. “These seats are the Everest of uphill climbs — seats that Republicans won by 20 points — which means that Democrats could go winless in special election season and still take back the House next year.”

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