Tim Evans, and Mark Alesia

IndyStar

Shortly after he moved to Jeffersonville last fall, Joseph Albert "Trey" Hollingsworth III had a problem only a GOP county chairman could solve.

The 32-year-old multimillionaire from Tennessee wanted to run for Indiana's 9th District congressional seat, but because he'd never voted in a primary here — let alone, perhaps, anywhere else — he needed the permission of an established GOP stalwart.

So he sought out Clark County GOP Chairman Jamey Noel. And Hollingsworth, Noel said, made one thing clear: If Noel didn't approve the candidacy, someone else would.

“I know he was looking at moving possibly to other parts of the 9th District," Noel said, "to find a county chairman that would sign off on him if I would not have done it.”

So Noel obliged, and Hollingsworth launched his campaign, supported by $1.5 million of his own money — and $500,000 of his father's, angering three opponents and setting off a series of questions.

The other GOP candidates in the 9th District Republican primary race — Attorney General Greg Zoeller, state Sens. Erin Houchin and Brent Waltz, and Robert Hall — have long histories in Indiana. And they're taking aim at the new arrival, with his background being the central question of the campaign.

Is Trey Hollingsworth a breath of fresh air, a successful businessman and political outsider? Or is he nothing more than than a rich Tennessee carpetbagger using his family wealth to try to buy a seat in Congress?

And, by the way, who is this new Hoosier who calls himself Trey?

Small-town southern boy

Hollingsworth grew up in Clinton, Tenn., a small town about 30 miles northwest of Knoxville. It is notable in part for the "Clinton 12," who in 1956 became the first African-American students to desegregate a public school in the South, a rancorous saga commemorated by a statue of the students.

Hollingsworth, however, didn't attend Clinton High School. He went to the private Webb School in Knoxville, Tenn., whose alumni include a former governor, a state Supreme Court judge, CEOs, the owner of the Cleveland Browns and professional athletes.

By all accounts, Trey lived what can fairly be described as a privileged life and his father, Joe Hollingsworth Jr., appears to have had big plans for his son.

Joe Jr. is known for soaring ambition, business acumen and political involvement in Tennessee. His name was mentioned as a potential candidate for governor in 1998 — as a conservative Democrat.

At the time, he was upset with the Republican incumbent, who did not heed the advice of an economic advisory committee Hollingsworth Jr. chaired.

The elder Hollingsworth, a long-time Democrat before switching parties, did not end up running. But he remained engaged in politics, giving money to various causes and candidates from both parties. Trey Hollingsworth said his father's record of political contributions shows he is a "staunch conservative."

In 2003, Joe Jr. wrote a book called “The Southern Advantage” that extolled the benefits of doing business in the South, without a strong union presence. The cover is a slice of the country on a map, with the southern states shaded and others, including Indiana, left blank.

In addition to business and politics, Joe Hollingsworth Jr. has a voracious appetite for adventure.

He was featured in Megayacht News in 2009 for his 29-day chartered cruise of the Caribbean aboard the 118-foot boat Savannah. He divided the trip into segments, inviting different groups of family and friends.

Joe Jr. also has a decades-long annual tradition of hosting an extravagant party before a University of Tennessee football game. A news account of the event in 2009 listed people who attended, including politicians. The Mayberry-themed party, described as the 32nd annual, had invitations delivered as a “summons” by an actor playing deputy Barney Fife.

His adventures aren't even limited to Earth. A 2012 story posted on his company's website described Joe Jr. as among 300 people who signed up for a space flight on Virgin Galactic. The price for the two-and-a-half-hour ride: $200,000.

Now he's spending heavily to help launch his son's political career.

Businessman Trey Hollingsworth, his dad spend heavily on Indiana 9th District seat

New super PAC goes after 'Tennessee Trey'

How I Got Rich On My Summer Vacation

Trey Hollingsworth made a mark early. When he was 15 years old, he was touted as someone to watch in a Washington Post article headlined “How I Got Rich On My Summer Vacation.” The story was about high school students in a summer entrepreneurship camp in Oregon.

Hollingsworth was working on an Internet start-up, according to the story, but he would not reveal details for fear someone would steal his idea. He told the reporter he worked on the business “from 1-3 a.m. each morning, after a daily marathon of classes, work on his high school yearbook, soccer and cross-country practice and four hours of studying.”

After Hollingsworth graduated from the University of Pennsylvania's prestigious Wharton School, his father set him up in business. The younger Hollingsworth's personal worth, according to campaign documents, is at least $58 million.

Hollingsworth said he raised funds for his real estate business at first by feverishly pitching potential investors and scouring the Midwest and South for vacant industrial sites that could be rejuvenated.

But his father also helped finance the start-up business. A press release from Hollingsworth Cos. noted that in 2005 "Hollingsworth Capital Partners was formed with Joe's son, Trey, as managing partner and majority owner."

The company grew rapidly, and was recognized by Inc. magazine in 2007 as the 12th fastest-growing private company in the U.S.

Hollingsworth's first business foray into Indiana came that year when he registered a company with the secretary of state. In March 2008, Hollingsworth’s business purchased its first Indiana property, a former Verizon warehouse in Westfield. The 33,000-square-foot facility had been listed for about $8 million.

That year, Hollingsworth and a group of partners opened Alexin, an aluminum casting plant in Bluffton, collecting more than $800,000 in state incentives from 2008 to 2012.

His opponents have touted that as an example of Hollingsworth having accepted "government handouts."

The company also received a 10-year personal property tax abatement, but missed a filing deadline in 2013 that prompted a two-year legal battle. In December, the Indiana Tax Court ruled his company — from which Hollingsworth reported earning an annual salary of between $100,001 and $1 million — owed more than $90,000.

Campaign records also show Hollingsworth received salaries in that same range from three of his other companies with Indiana ties — in addition to earning between $1 million and $5 million from Hollingsworth Capital Properties.

Hollingsworth said he's entering politics because Washington needs people with his business experience and he's frustrated that government "is no longer by the people and for the people. Instead, it's by politicians and for politicians."

But when he presumably votes for himself in next month's primary, it might be the first time Hollingsworth has voted in a primary election — ever, at least according to Tennessee public records. They show Hollingsworth having registered to vote in 2004, but only voting in general elections that year and in 2009.

Hollingsworth disputed those records, saying "based on my recollection" he has voted in a primary before.

"I'm certain I have and I'm equally certain these records continue to be poorly maintained by the states and dumped inappropriately, voided when one moves," Hollingsworth said.

IndyStar provided Hollingsworth's campaign with his Tennessee voting record, but it did not respond or provide any other documentation.

Hollingsworth explained his move to Indiana as something that was in the works before he registered to vote last September. He said he and his wife are planning to start a family soon and wanted to be close to her family in Louisville.

He also noted that his business has operations in Indiana.

Hollingsworth said he established residence in the state "early or middle of last year." Asked what his last residence was before moving to Indiana,

Hollingsworth was evasive.

"I'll have to go back," he said, "and check the record."

He said a campaign spokeswoman would provide that information, but no one from the campaign got back to IndyStar.

'He's a carpetbagger'

Hollingsworth's jump into the congressional race so soon after landing in Indiana is unprecedented, said Andrew Downs, director of the Mike Downs Center for Indiana Politics. But it is legal.

Indiana election law requires congressional candidates to be residents of the state, but they are not required to live in the district they seek to represent. They also have to "prove" they are a Republican or Democrat, typically by a primary voting record.

For newcomers such as Hollingsworth the law allows the party chairman in the candidate’s home county to vouch for their affiliation. That's why Hollingsworth sought out Noel soon after he and his wife established residence at a luxury high-rise in Jeffersonville.

"Of course he’s a carpetbagger," Downs said. "It's an easy label to hang on him. The amount of time he’s been in the state is so short. That doesn’t mean that he doesn’t have good ideas, that he doesn’t have positions worth discussing or anything like that."

Downs said that if someone were interested in trying to buy a congressional seat as an "outsider," this is the perfect year to do it. And the 9th District GOP race is the ideal venue. It is a solid GOP district and the incumbent, Todd Young, is giving up the seat to run for the Senate.

“It’s a very good year to be an outsider," Downs said. “He could actually do well if Trump does well here.”

Downs said Hollingsworth has another advantage in the crowded race. He doesn't need to get 51 percent of the vote to win the nomination.

“Any time you have three or more," Downs said, "suddenly 28 percent, 34 percent, those are winning numbers."

Down to the wire

Whether the business success Trey Hollingsworth and his father have achieved translates to politics will be decided by voters next week.

The candidate Republican voters select May 3 in the district — stretching from Johnson County to the Ohio River — is likely to end up representing Hoosiers in Washington. The 9th District is heavily Republican.

Hollingsworth has spent heavily on television ads and mass mailings to portray himself as a conservative, Christian, pro-business, anti-Obama, political outsider. The PAC ads financed by his father have bolstered that image, while attacking Zoeller as a career politician.

The family's funding of Trey Hollingsworth's campaign — which as of April 13 collected only $1,500 from Hoosiers — spurred formation of a competing PAC that launched a series of radio ads last week. Ads from the new PAC, Frugal Hoosiers, attacked Hollingsworth as a carpetbagger dubbed "Tennessee Trey."

"He thought he could just waltz in last fall and buy an Indiana seat in Congress," one of the ads says. "He's even been using one of those secret super PACs to try and do it."

The ads don't endorse any of Hollingsworth's opponents, but conclude with a pointed message: "Vote no on Tennessee Trey Hollingsworth. And send a Hoosier to Congress instead."

Hollingsworth responded, "Elections are about the future and where we want to go, not about the past and not about geography."

Contact IndyStar reporter Tim Evans at (317) 444-6204 and follow him on Twitter: @starwatchtim. Contact IndyStar reporter Mark Alesia at (317) 444-6311 and follow him on Twitter: @markalesia.