Last September, Joseph Albert Hollingsworth III, better known as Trey, registered to vote in Jeffersonville, Indiana. He had moved from South Carolina, though he is by birth and most any other measure a Tennessean. By October Hollingsworth was running for Congress in the Indiana 9th, a mostly rural (and safely Republican) district that stretches between Indianapolis and Louisville. Hollingsworth is a 33-year-old businessman. He is worth at least $58.5 million and probably much more; even that first number would make him one of the Congress’s richest members. And Hollingsworth really, really wants to be a congressman. On May 3, the day Trump clinched his nomination in Indiana, Hollingsworth won a five-way GOP primary. “Tennessee Trey,” as both Republicans and Democrats have taken to calling him, has now loaned his campaign almost $3 million. A friendly super PAC has added a million more.
Historically, a carpetbagger was a Northern opportunist who moved to the Reconstruction South, hoping to seize wealth and power. This makes Trey Hollingsworth a neat inversion in that he’s a Southern opportunist who’s come to prey on the North. It’s become an interesting experiment in Indiana: If spotted a personal fortune, a sophisticated campaign, a gerrymandered district, and a squishy campaign finance system, can a man literally buy himself a seat in Congress?
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Hollingsworth has a perfect candidate biography, if only he were running in Tennessee. He was born in 1983 and grew up near Knoxville, in the small town of Clinton, where his father operated an industrial development firm, the Hollingsworth Companies. Joe Hollingsworth Jr. clearly loved his business, his family, and the South. He gave money to politicians from both parties and cultivated a large influence in local politics; some thought he might run for governor, though he never did. Joe owned a 118-foot yacht and named it Savannah. Each year, he threw a lavish Big Orange gala to celebrate the University of Tennessee’s football team.
At those galas, Trey Hollingsworth would often serve as a host, mingling among the orange jerseys and the Mayberry-inspired décor. He attended a private school in Knoxville, where he rowed, played soccer, and demonstrated an astonishing degree of ambition. One summer, when he was 15, he went to a summer camp for young entrepreneurs. Hollingsworth told a reporter there that he tried to sleep only three hours a night in order to work on his internet startup. But he refused to describe the startup itself since he was worried someone might swipe his idea.
Hollingsworth never did make it to Silicon Valley. Instead, he went to Wharton, then started a new company shortly after graduation. His father played a crucial role. While the Hollingsworths have not shared many details from this period, an old press release on his father’s website says, “Hollingsworth Capital Partners was formed with Joe’s son, Trey, as managing partner and majority owner.”
The passive voice is doing a lot of work in that sentence. But regardless of how much help Hollingsworth got, he became a successful businessman in his own right. His company has specialized in finding and refurbishing abandoned factories and warehouses from all over. Much of Hollingsworth’s wealth now comes from his real estate holdings in Indiana, Ohio, Michigan, Kentucky, Georgia, South Carolina, North Carolina, Alabama, Virginia, and of course Tennessee, among others.
At some point, Hollingsworth identified another neglected asset: Indiana’s 9th Congressional District. Last summer, the incumbent, Todd Young, announced he was running for the U.S. Senate, opening up a district that Republicans had redrawn after 2010 and that Young had carried by 28 points in 2014. Hollingsworth seems to have been living in South Carolina at the time; he’d married his Louisville-born wife there, in a garden party-ish ceremony at Charleston’s Lowndes Grove Plantation, complete with “Southern-style hors d’oeuvres.” But it wasn’t long before Hollingsworth moved to a rented luxury condo in Jeffersonville, a town just across the river from Louisville. Because he’d never voted in a Hoosier primary, Hollingsworth needed the blessing of a Republican county chairman before he could legally run for Congress. He called the chairman in Jeffersonville’s Clark County, though at first Hollingsworth refused to give his name. He also hinted that if the chairman didn’t sign off on his candidacy he could just move to another county in the 9th District where someone else would. The chairman agreed to help, provided Hollingsworth sign a GOP loyalty pledge.
Once approved, Hollingsworth hit the trail hard. His campaign in short order hired a media firm from New Jersey; a financial firm from San Diego; an opposition research firm from Dallas; and a pollster, a lawyer, and a digital media specialist from Washington, D.C. By the end of 2015, Hollingsworth had given or loaned his campaign $685,577. In that same period, his campaign reported exactly one donation from an Indiana resident, a thousand bucks from a Jeffersonville retiree.
Most of Hollingsworth’s money went to TV ads, and on this front he received some mysterious help. His media firm started throwing sumptuous B-roll up on YouTube—Hollingsworth touring his Indiana industrial sites, Hollingsworth sitting in his expertly staged condo, Hollingsworth strolling through downtown Jeffersonville with his wife. In January, a new super PAC, Indiana Jobs Now, began running commercials that used this footage. No one knew who was behind the super PAC until it filed its first quarterly Federal Election Commission report in April. All of the money, eventually more than a million dollars, had come from Joe Hollingsworth Jr. It’s hard to think of a better campaign finance farce than a father supporting but not “coordinating” with his son.
The ads provided a huge advantage. One thing that’s helped Hollingsworth in the 9th District is that the only way to get real TV coverage is by making expensive and inefficient ad buys in Louisville and Indianapolis. Hollingsworth’s financial edge let him run so many commercials that Jeffersonville residents soon recognized the footage of him walking their city’s streets—even though no one in town seemed to have had any interaction with him in real life.
Another perk of the 9th District is that it doesn’t have much local media, and Hollingsworth frequently dodged what media there was. When he did agree to interviews, he often evaded, even on seemingly benign questions. He declined to release his tax returns. When someone asked him to name his three favorite Hoosiers, he declined to do that, too. One reporter asked him where he’d lived before moving to Indiana; “I’ll have to go back,” Hollingsworth said, speaking about his own life, “and check the record.” Pressed on when exactly he moved to Indiana, he finally answered with early summer. Another reporter tried to clarify whether that meant June or July. “I think that’s a good characterization,” Hollingsworth said.
Still, Hollingsworth eventually settled on an effective message. One of the stranger things about his congressional dreams is that Hollingsworth doesn’t have much history of political interest or ideology. The Indianapolis Star found no trace of his having ever voted in a Tennessee primary, Republican or Democrat. But on the issues, he opted for standard Republican—Christian, conservative, angry at Obama. On his background, he said he moved to Jeffersonville to be closer to his wife’s family in Louisville. (Of course his earlier threat to move elsewhere in the 9th District complicated that story.) He talked about the 11 years he’d spent renovating businesses in Indiana, and he never mentioned his holdings in many other states.
In a crowded primary, that was enough. His Republican opponents called him a “carpetbagger” and “Tennessee Trey” and even a “political scam artist.” But Hollingsworth won with 34 percent of the vote. As of this writing, he has given his campaign $102,072 and loaned it another $2.7 million. He is also in a dead heat with the Democratic candidate, Shelli Yoder, who grew up in Indiana, teaches at Indiana University, and is a former Miss Indiana to boot.
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I happen to live in the 9th District, and one October day I drove to Brownstown, Indiana, to watch Hollingsworth interact with some Hoosiers.
Brownstown (population 2,947) is the kind of place where you see a few signs for Hillary Clinton, a fair number for Donald Trump, and an overwhelming number for the high school football team (currently ranked ninth in 3A!). It’s one of the nicest county seats in the district, with a downtown that’s small but mostly full, and a big reason for all this civic spirit is Brownstown’s Exchange Club. Each Tuesday, the club meets at Michie’s Diner to eat breakfast, plan its latest community fundraiser, or talk with a guest.
On the Tuesday I visited, there were about 15 members in attendance, most of them retired or close to it. Hollingsworth showed up early, wearing nice jeans and a smart button-down. In his TV ads he can seem a bit robotic, but in person he quickly revealed himself to be an excellent retail politician. It helped that he’d had lots of practice; according to his campaign, he’s called 15,000 voters and knocked on 25,000 doors.
Once it was time to start, everyone stood up. Hollingsworth hammered his hand over his heart—a bit too quickly since the sequence was actually prayer, then pledge. Those preliminaries completed, he began to talk. “My campaign’s about two things,” he said. The first was his business background. “I’ve been building and renovating businesses in Indiana for 11 years,” he said, and he explained his frustrations with America’s tax code and over-regulation. He promised he could keep jobs “from going overseas or, God forbid, going to Illinois.”
The second thing was public service. Too many in Washington were political insiders—people worried about moving to a corner office “instead of serving Hoosiers.” It was odd to see someone who’d spent so much time and money in search of a congressional seat accusing others of careerism. But Hollingsworth also promised to push for term limits. In fact, he signed a term-limits pledge at each door he knocked on. After four terms, he said, he would “re-engage with the private sector.”
Hollingsworth agreed to take questions. At first it went as you’d expect in a small Midwestern town. The first question was on immigration. (“I believe the first step,” Hollingsworth said, “is securing our Southern border.”) The second was on federalism and returning power to the states. (“A bureaucrat a thousand miles away doesn’t know how to solve Brownstown’s problems.”)
Before long, though, the discussion shifted. One person asked about Obamacare. “I’m a repeal-and-replace guy,” Hollingsworth replied. But that elicited only more responses. Another person pointed out that the law guaranteed a range of benefits, including the 80/20 rule, the ban on gender rating, and coverage for pre-existing conditions. Hollingsworth—and a couple of the club’s more conservative members—offered counterpoints, including the number of insurers leaving the marketplace and the fear that doctors were facing new restrictions on what services they could provide.
One man, whom everyone called simply “pastor,” emerged as Hollingsworth’s main interlocutor. The pastor, whose name is Kevin Stiles, explained how he’d retired from Brownstown’s United Methodist Church, which meant he and his wife had lost their insurance. While he’d returned to the pulpit part-time, they hadn’t been able to find coverage because his wife’s heart problem was considered a pre-existing condition. They’d spent a year in financial and medical terror, until Obamacare came along. Hollingsworth listened patiently but took a longer view. “I don’t believe government mandates and government monopolies will deliver the best outcome over the long term,” he said.
“Right, now my wife is insured,” Stiles replied. “Before she wasn’t.”
“A single instance doesn’t mean it’s working,” Hollingsworth said.
“That’s the instance I care about.”
We were reaching some kind of philosophical limit—a place where two worldviews simply couldn’t be reconciled. Still, the conversation had been civil and deep and free of cross talk. It was a nice reminder that even in place like Brownstown, a place that had gone for Romney by more than 20 points, there were still hundreds of people who’d voted for Obama and then found a way to get along with their neighbors, and their neighbors with them.
There was one more lively exchange that morning. “Would you agree that money is a corrupting influence in politics?” another left-leaning club member asked.
“I do not know that I would say that,” Hollingsworth said. The candidate who had seemed so crisp, talking health care and cracking jokes about Illinois, turned abstract and evasive. He started sounding a lot like he did when reporters inquired about his old addresses. Someone brought up the Koch brothers and their right to spend their money—to express their free speech. “That’s an argument that’s been made,” Hollingsworth said, “and I have some sympathy with it.” But couldn’t that kind of money buy a politician’s ear, asked someone else? “I think it’s a fair point,” Hollingsworth said, “and there are a lot of people who are concerned.”
What was striking about the conversation (and the whole morning) was that it could’ve taken place anywhere—in Indiana or Tennessee or South Carolina or any other state. No one asked Hollingsworth about his money corrupting politics, and no one asked about his relocation, either. I don’t think this was just Hoosier politeness. Hollingsworth’s biography clearly bothers some voters. After all, the race is close, and in one recent poll of the 9th District a quarter of respondents brought up the carpetbagging by themselves. But educated and passionate voters like the guys in the Exchange Club? They care more about partisan issues. Later, when I asked them about Hollingsworth’s Tennessee-ness, they all admitted they’d been thinking about it at the breakfast. One guy said he’d listened for any traces of a Southern accent. (It’s gone.) Another conceded that Hollingsworth’s move made him uncomfortable. But then he turned defensive. “Hillary Clinton broke the mold when she ran for Senate in New York,” he said. “She’s a lot more of a carpetbagger than Trey.” Even the pastor said that Hollingsworth’s move didn’t bother him as much as his ideas. I asked if he’d vote for Yoder, the Democrat, if she were the carpetbagger. “I’d probably do it with a guilty conscience,” Stiles said, “but I’d still vote on the issues.”
Hollingsworth may not get his seat, but there’s no question his bid was made easier by the fact that, more and more, all politics is national. There are lots of reasons for this—the gravitational pull of the presidential election, the hyperpolarization of our politics in general, Congress’s post-2010 ban on earmarks. Earmarks let representatives score cash or tax breaks for pet projects, often back home in their districts. A pork-free or pork-light politics is a politics coming unmoored from the straightforward votes-for-stuff transactions at the heart of local representation. In their place we get appeals to our tribal (i.e., national) loyalties. In the Indiana 9th election, neither Yoder nor Hollingsworth has spent much time talking district-level issues. When Yoder has hit him on the carpetbagging, he’s countered by linking her to Clinton and the Democrats. Joe Hollingsworth’s super PAC has even given her her own alliterative nickname: “Socialist Shelli.”
At the Brownstown breakfast, Hollingsworth fielded other questions, on Social Security and Syrian refugees. But eventually he had to head to his next campaign stop. There was time for one last order of business: the weekly drawing. The Exchange Club has been doing this for years now. At the start of each breakfast, the members chip in a buck apiece, with half the pot going to charity and the other to the winner of next week’s drawing. Stiles asked Hollingsworth to do the honors, and the candidate reached in and drew a name out of an old Folger’s can: the club’s secretary, Steve. Before anyone could congratulate him, Steve admitted that he’d skipped last week’s meeting and shouldn’t be eligible. He proposed they roll the prize over to the next breakfast. “Now that,” someone said, “is an honest man.”