His first deal on Hilton Head Island was for South Island Square, when the shopping center was anchored by one of the original Longhorn Steakhouses in the spot that’s now the Lucky Rooster.
That was in the 1980s and Millard Vaughn Oakley of Livingston, Tennessee, population 4,000, was just launching a real-estate investment career that would bring him great wealth — and help anchor the island economy.
Oakley was a 91-year-old recovering country lawyer when he died April 21, a few days after suffering a stroke.
He was the youngest of seven children born into a family with deep roots in the historically poor Upper Cumberland area of eastern Tennessee. As a young child, there was no indoor plumbing in the house that his daddy ended up losing altogether during the Great Depression.
Oakley was elected to the Tennessee legislature at age 22, not long after he bought his first business at age 15, a three-seat shoeshine stand on the square in Livingston.
He parlayed a colorful mix of people skills and shrewd business sense into becoming one of the largest benefactors of the university he would have flunked out of if he hadn’t convinced the president it would break his mother’s heart to be sent home.
He would end up being one of the area’s largest philanthropists, giving millions to its schools and the town library.
Oakley saw business as “horse trading,” and he preferred it to taking depositions and hammering out contentious divorces in a courtroom where he would have known the mama, uncle and cousin of everybody there.
He held politically appointed positions in Washington, D.C., and Knoxville, but it was the give-and-take of the marketplace where he flourished.
He owned an $800 million bank though he never banked a day in his life.
And he bet big on Hilton Head for decades. And won.
Oakley owned The Boathouse, a dry stack boat storage, service and sales business on Squire Pope Road that he recently expanded by 80 slips as the boating industry booms. The Boathouse now has three locations, including the former Stuckey’s Furniture building in Okatie, but Oakley’s property on the Intracoastal Waterway is best known for his prized tenant, the local SERG Group’s Skull Creek Boathouse restaurant.
Oakley owned more than a dozen units in the Village at Wexford shopping center.
He has owned a number of the buildings lining New Orleans Road, a key commercial corridor on the island’s south end. And he owned office space surrounding Hilton Head Hospital.
Most recently, he righted the ship at an island institution in what may become his most long-lasting contribution to the local economy.
Oakley bet big on Palmetto Bay Marina, one of the island’s oldest and most storied docks that supports a ring of condos, restaurants and small businesses on Broad Creek. The piers had suffered great damage from Hurricane Matthew in 2016, and even more damage from failed ownership that left it a wreck.
It took 18 months to negotiate the complex web of ownerships and claims on the property. And he spent millions more repairing and expanding the dock.
Betting on Hilton Head
Oakley’s passing a week prior to his 92nd birthday was major news in Tennessee.
Former U.S. senator and ambassador to China Jim Sasser spoke at his funeral.
It wasn’t much noticed on Hilton Head.
But Oakley believed in Hilton Head, owned a home in Wexford, and enjoyed to the fullest the local businesses he touched as a landlord — and excursions with friends aboard his 45-foot center-console Grady-White with four 425-hp engines.
Oakley leaned on an innate ability to judge business risk and personal character in buying property around the Southeast, often capitalizing on the fallout of the savings and loan failures of the 1980s and 1990s.
“He always saw promise in Hilton Head,” said Kuy Scott, who runs Palmetto Bay Marina. “He thought for years maybe it had been slightly overlooked.”
A week before he died, Oakley was on Hilton Head addressing a major problem for the local businesses he felt so much a part of: the lack of workforce housing. He was looking at buying land where affordable housing could be developed.
And those close to him say that could still happen.
Oakley “went 180 mph till the end,” Scott said.
“He hadn’t had to work in 40 years, but at 91 he was here trying to solve workforce housing.”
‘Start all over’
Oakley was asked in a PBS interview by Becky Magura why he always worked.
“When I was little some of the kids had ice cream and I didn’t have any and I didn’t like that very much,” he said.
He characterized himself as stumbling into opportunity, and always having a partner who did the work.
He got into the radio industry when an engineer owed him money for legal work, but gave him a license instead.
He said he was a minor contributor to the founding of the First National Bank of Tennessee, investing only about $40,000 and eventually buying out the other five founders.
He talked of big failures — specifically the Renegade Resort in Tennessee, where the main attraction of skiing failed because it didn’t have enough altitude.
“You just get up and start all over,” he said. “When you start with nothing, it can’t be too bad.”
He said the key to success is choosing the right people to associate with.
“I always try to get in with people in a deal who are smarter than you are, and then give it some thought. I’ve noticed you get lucky. I’ve always noticed the harder you work the luckier you get.”
‘It wasn’t all about money’
He was introduced to the Hilton Head market by longtime commercial real estate agents John Scott III and Spain Kelly.
“He was really smart,” said Scott, Kuy Scott’s father and a 40-year friend of Oakley and his wife, J. Annette “J.J.” Oakley. He worked with Oakley on local purchases through his MSK Commercial Services firm.
“He could size things up pretty fast. He had the wherewithal and ability to make things work. He had a special skill set. He could see things other people did not see.”
Kuy Scott and Grant Kaple, general manager of The Boathouse, were pallbearers at Oakley’s funeral in Livingston on April 24.
Kaple said Oakley brought out the best in his associates, but he wasn’t an overbearing boss or landlord.
“He was an ‘if it ain’t broke, don’t fix it’ kind of guy,” Kaple said.
He said Oakley told him he’d lost more money not doing a deal than he ever did in the deals. He always called his deals “trades,” even when money was involved.
Rob Jordan, a partner in the SERG Group of restaurants that is Hilton Head’s largest employer, said, “He wanted to see us succeed.”
Jordan said Oakley didn’t like the famed golf or beaches of Hilton Head.
“He liked the people,” he said. “It wasn’t all about money. It wasn’t all about property.”
David Lauderdale may be reached at LauderdaleColumn@gmail.com.