SEYMOUR, INDIANA — Thirty one days out from the election, where he would try to unseat a two-term incumbent congressman, Andy Ruff waited for the voters of Jackson County to come to Gaiser Park and hear him out. No one showed, except for his ex-wife and a friend.
Ruff, 58, is a former 20-year Bloomington city councilor and honky-tonk musician on the side who is challenging current Rep. Trey Hollingsworth, R-9th District. He planned on spending the afternoon of Oct. 3 in the park playing music with his band, the Dew Daddies, and hanging out with voters in Indiana’s 9th Congressional District.
The event wasn't advertised well enough, he said, so they weren't expecting much of a turnout. The Facebook event page listed it for 3:30 a.m. instead of 3:30 p.m., but he went anyway in case anyone showed up.
A group of men played a game of horseshoes in the background, enjoying a quiet afternoon at a local park. Some kids kicked around a soccer ball, at times near the campaign’s table set up under the park shelter house.
Ruff’s race isn’t considered competitive. Across tens of thousands of simulations of the election, as forecasted by statistics website FiveThirtyEight, Ruff wins 2% of the time.
He said he knows some people in the district would reject him outright for being a progressive, universal health care-supporting Democrat in a reliably red state, but he’s running in part because he’s confident he can connect with voters on policies outside of party labels, when he can meet them face-to-face.
“People will say, ‘Oh, so you're a liberal,’ and I'm saying, ‘I'm not a label,’” Ruff said. “I am a person who's been here my whole life and interacted with ordinary people in Southern Indiana my entire life and has shared experiences and shared background and shared perspectives and shared values and shared beliefs. And I believe that we all want to move forward.”
Finding common ground out in the district was a much more achievable campaign strategy before the pandemic. Originally, Ruff envisioned campaigning at local fairs and festivals and across the district, playing music and connecting with voters beyond traditionally liberal-leaning Bloomington.
But the planned “Ruffhouse Tour” was forced to adapt its strategy after the COVID-19 pandemic caused mass cancellations this spring and summer and severely thinned the crowds of could-be constituents Ruff was planning to connect with one-on-one.
He’s made appearances where he can, through a slate of his own events and remaining community events such as farmers markets across the district.
The Gaiser Park appearance was scheduled alongside “No Fest,” a small socially distanced festival at local Brooklyn Pizza Company meant to stand in for the city’s canceled annual Oktoberfest. Ruff played and spoke there earlier to a decent sized crowd as that day's opener, but was accidentally only promoted by the festival as an appearance by the Dew Daddies instead of as a Congressional candidate.
Booths, food trucks and tables filled the lot behind Brooklyn Pizza, including a table for the Ruff campaign across from a lemon shake-up stand.
Near the table, Ruff started talking to three women, a grandmother, mother and granddaughter from Brownstown, Indiana, and giving them his pitch: He’s from the district, he’ll work for ordinary Hoosiers because he is one, take some literature and learn more.
The oldest of the three women, 67-year-old Becky Boas, hadn’t heard of Ruff before but said she was impressed with his approachability and would probably vote for him.
“He seems down to earth, not a politician,” she said. “He’s not running in a suit and tie.”
They took handouts with Ruff’s platform listed on the back with his slogan: In tune with Indiana.
“I appreciate you giving me a chance,” he said as they walked away.
As it became increasingly clear the campaign wouldn’t have as many opportunities to meet people in the now-distanced district, Ruff settled on his next step: he would campaign through song.
Written by Ruff and released in July, “Tennessee Trey” is criticism via country music. He filled the song with details about Hollingsworth’s voting record and personal history, including supporting a tax cut bill that benefited the wealthy, his comments on the pandemic from April and getting married on a South Carolina plantation.
Hollingsworth moved to Indiana’s 9th District from his home state Tennessee shortly before running for office, stoking criticism from both sides that he was a carpetbagger swooping in to "buy" the district. Ruff’s song embraces the dig.
“Tennessee Trey, Tennessee Trey, gonna send you back to Tennessee on Election Day,” Ruff sings in the chorus. “For the volunteer state you might be okay, but we need a Hoosier in the House, not Tennessee Trey.”
The music video features Ruff’s son Hank, a senior at IU, playing guitar and singing alongside him. Hank grew up running around in the city council chambers and playing music with his dad, eventually majoring in political science and interning for the late Rep. Elijah Cummings, D- Md., and forming his own band, Hank Ruff and the Hellbenders. He now joins his dad for musical appearances on the campaign trail, digital or otherwise.
Ruff was born and raised in Bloomington, and said he gravitated toward nature:
riding his bike out to Griffy Lake and fishing in the morning as the sun rose, swimming when it got too hot to fish, eventually staggering home sunburned and happy. He graduated from Cornell University in 1987 with an undergraduate degree in natural resources, wanting to work in the outdoors.
A bad car accident kept him from accepting a post-graduation job offer with the U.S. Forest Service, and he was a teacher at North Central High School in Indianapolis for a year before moving back to Bloomington and getting involved with local government.
At first, he was a concerned citizen strongly opposed to the proposed, and now years underway, expansion of Interstate 69, and later — he said at the urging of the local Democratic Party and former Bloomington mayor and six-term Rep. Frank McCloskey, who represented the 8th District when it included the city — he won a seat on Bloomington City Council in 1998.
While on the council, Ruff was key in developing Bloomington’s living wage ordinance, which requires the city, its contractors and beneficiaries of city subsidies to pay employees a calculated, annually increasing living wage now standing at $13.21.
Ruff now sells himself as “an anti-establishment Hoosier progressive,” an often-repeated tagline, and his platform includes endorsing a Medicare for All style system, legalizing marijuana, addressing climate change and keeping big money out of politics.
Hollingsworth said in a recent interview with WTIU/WFIU that despite Ruff’s local background, his policies don’t match the interests of voters in the district.
“I think that what people care about is someone matching their values and focused on their priorities,” he said. “And I think if Mr. Ruff traveled outside of Bloomington's city limits nearly any time, he would recognize that the rest of the district feels very differently about socialized medicine than his proposals.”
Hollingsworth’s campaign is instead emphasizing economic recovery from the pandemic and keeping the country the land of opportunity by avoiding what he called “a more socialized-focused government.”
Ruff said he has to explain to some voters he meets that his policies aren’t socialist, but in line with Midwestern values.This realignment is a key strategy for Ruff. After all, isn’t it the Hoosier thing to care about your neighbor?
“They say, ‘Well, I don’t want socialized medicine, but don’t you dare do anything to my Medicare,’” he said. “I say, ‘Wait a minute. That’s exactly what we’re talking about. Do you consider public schools to be socialism?’”
Starting conversations across partisan lines can be difficult, Ruff said. It’s why he’s made music such a central part of the campaign: it’s a way to crack open the door.
If someone watches “Tennessee Trey” and likes the same country music Ruff has loved his whole life, ever since he would listen to Johnny Cash and Roger Miller on the eight-track player in his dad’s green Mercury Montego as a child, he said maybe they’ll see he’s not a monster — just a Democrat.
Ruff isn’t the first progressive to try to unseat Hollingsworth. People remind him about the 2018 midterm elections all the time, when Hollingsworth defeated Democratic labor attorney Liz Watson.
Watson, who was born and raised in Bloomington, generated national excitement as a young, progressive woman trying to flip a red district as hype built for Democrats ahead of an expected "Blue Wave." Sen. Bernie Sanders, I-Vermont, even campaigned for Watson in IU's Dunn Meadow.
The Blue Wave gave Democrats a sizable advantage in the House of Representatives, but didn't touch Indiana’s 9th District. Hollingsworth kept his seat, winning 56.5% of the vote.
A little over a year later, and seven months after he lost his city council seat to IU graduate student Matt Flaherty, Ruff announced his campaign in late 2019 after checking that Watson and her 2018 primary opponent Dan Canon weren’t challenging Hollingsworth again.
“We felt like standing idly by and watching that opportunity pass would be more painful than running,” Ruff’s wife Susan Bollman said.
While in office, Hollingsworth has mostly voted across party lines, including voting against impeaching President Donald Trump, expanding the Affordable Care Act and extending housing assistance during the pandemic. His website says he believes in shrinking government, Christian family values and America.
He made national news in April after telling Indiana radio station WBIC that while he appreciated the input of scientists, prioritizing reopening to get Americans back to work was “the lesser of these two evils.”
“It is policymakers’ decision to put on our big boy and big girl pants and say it is the lesser of these two evils,” Hollingsworth said. “It is not zero evil, but it is the lesser of these two evils and we intend to move forward that direction.”
Ruff said the comments and the political climate of the pandemic itself make Hollingsworth a different candidate than he was two years ago.
And, Ruff said, isn't he with his flannel shirts and country music a different kind of candidate than Watson, a Georgetown-educated lawyer and policy adviser with D.C. bonafides? Wouldn't that have a different appeal in some parts of the district?
“It all adds up, to me, to be a very different election cycle than 2018,” he said.
Most mornings, Ruff says, he tries to be at his computer within 30 seconds of waking up, chipping away at the mountain of tasks a Congressional campaign entails.
One day, a little over two weeks out from the election, revolved around a two-hour drive to New Albany, Indiana, and back for a radio interview to reach voters in the southernmost part of the district. Later, Ruff and Bollman would head up to Avon, Indiana, not for the campaign, but to take their turn spending the night with Bollman’s father, who has advanced Parkinson’s and needs nightly in-home assistance.
Ruff’s schedule is largely guided by a list he handwrites every night of tasks for the next day: calls to prospective donors whenever possible, thank you notes to staffers, all the politicking he can fit around his life and day job as an academic adviser for students studying human biology at IU.
Before he hit the road that morning a little after 10:30 a.m., he already fit in advising sessions with five students. Another night, he had an 11 p.m. call with a student.
That evening, heading up to Avon, Bollman drove so Ruff could fit in some extra donor calls. Bollman said her chief role in the campaign is driving her husband around the district, talking strategy and direction as they roll along.
As an academic adviser running against a wealthy incumbent, Ruff is working with a fraction of Hollingsworth’s resources. Hollingsworth's campaign has received more than $1 million since Jan. 1 compared to Ruff’s $122,843.10, which includes $1,000.40 in candidate contributions.
The lack of funding means money goes where it’s most needed. Ruff had a full-time campaign manager at first, but said he decided after the primaries that the money could be better used elsewhere. The campaign now runs on a committee structure, with committee heads each paid a smaller amount for captaining a specific aspect of the race.
There isn’t money for full-time hires, communications director Jake Rossman wrote in an email. The campaign has seven or eight people consistently on-call who have been paid once or twice they refer to as staff and more than a hundred volunteers, including IU students.
If Ruff isn't careful, he can miss a schedule item entirely. One night, he was visiting his elderly parents’ house in Bloomington after an event, a rare moment to relax and just talk to mom and dad, when he glanced down at his phone.
“Andy, you’re supposed to be on a Zoom fundraiser call right now,” read a message from a staff member. He unsuccessfully tried to join on his phone before racing home to join late and apologize profusely.
The campaign decided to not spend money on polling, either. Bad results would just dishearten the campaign team, Ruff said, and good results wouldn’t change anything.
“Say that it said I had a chance,” he said. “Are we going to work any harder? No. We can’t work any harder. We’re doing everything we can.”
Nestled between Tunnelton Road and U.S. Route 50, the six arches of Bedford, Indiana’s Otis Park bandshell was hand-cut from hundreds of tons of local limestone and built in the 1930s, as part of the New Deal's Works Progress Administration, to highlight whatever takes place at the center of the stage.
The day before, it had been a wedding. On Oct. 18, 16 days out from the election, it was Andy Ruff for Congress.
With yard signs flanking the stage and a banner of Ruff holding a bass he caught secured across the front with bungee cords, they waited for Lawrence County to show up. Some did, less than 25 in all, trickling in to sit on yard chairs and blankets in the asphalt lot in front of the stage, but it was enough. Kim Grey, Ruff's ex-wife and Hank's mom, stood a few feet from the bandshell, recording the show on an iPhone at his request.
Clarice Guy, event attendee and Lawrence County Democratic Party Chair, said she’s seen Ruff connect with voters across party lines firsthand, but she's expecting the county to go to Hollingsworth.
“We may not see a big crowd, but we're going to give it all we got,” Ruff said at the opening of the show, having changed from a casual outfit into his specially embroidered Western shirt, part of a collection he shares with Hank, ready to honky-tonk.
Accompanied by Hank on vocals and the electric guitar, the band played a mix of covers such as John Prine’s “Paradise,” and original songs, including tracks from the Dew Daddies' albums and “Tennessee Trey.”
The Bedford concert wasn’t supposed to happen at all. It was originally canceled after a prediction of rain and low temperatures.But as the skies cleared, Ruff decided the concert should go on after all. Despite a fear of low turnout from a reversed cancellation, he figured they should go through with it: they had the bandshell reserved and it was the final stop of the Ruffhouse Tour, the campaign’s last in-person event before the election.
“We’ll do the best we can,” Ruff said before the show, while unloading audio equipment himself.
Every day brings another to-do list, more to chip away at as the election grows closer and closer.
The Ruff campaign’s priority now is trying to get as much material out as possible: paying for the “Tennessee Trey” music video to be a promoted post, sending one last targeted mailing to independents and Republicans they might be able to sway.
Ruff is realistic about his chances. He said his confidence has been shaken by seeing polls placing Trump still comfortably ahead in Indiana as the election approaches, and he can’t expect many voters to not vote straight ticket. But there’s always a chance.
“Maybe it won’t be that way,” he said. “Maybe the polls are wrong. It could be that there’ll be a surge, and people come out and while they’re out voting to get the country back on the rails, by getting Trump out of office, they’ll vote for me, too.”