Successful Hilton Head SC businessman dies at 91

His first contract on the island of Hilton Head was for South Island Square, when the mall was anchored by one of the first Longhorn Steakhouses in what is now the Lucky Rooster.

It was the 1980s and Millard Vaughn Oakley of Livingston, Tennessee, population 4,000, had just launched a career in real estate investing that would bring him great wealth and help anchor the island’s economy.

Oakley was a 91-year-old recovering country lawyer when he died on April 21, days after suffering a stroke.

He was the youngest of seven children born to a deeply rooted family in the historically impoverished Upper Cumberland region of eastern Tennessee. As a young child, there was no indoor plumbing in the house which his father ended up losing completely during the Great Depression.

Oakley was elected to the Tennessee legislature at age 22, shortly after buying his first business at age 15, a three-seat shoe shine stand in Livingston Square.

He used a colorful mix of interpersonal skills and business acumen to become one of the university’s biggest benefactors from whom he would have been dismissed had he not convinced the president that it would break his heart. of his mother to be sent home.

He would end up being one of the area’s biggest philanthropists, donating millions to his schools and the town library.

Oakley viewed business as “horse trading,” and he preferred it to taking depositions and hammering out contentious divorces in a courtroom where he got to know everyone’s mom, uncle, and cousin there. -down.

He held politically appointed positions in Washington, DC and Knoxville, but it was the market concessions where he thrived.

He had a bank of 800 million dollars although he never cashed a single day in his life.

And he’s been betting big on Hilton Head for decades. And won.

Oakley owned The Boathouse, a dry-cell boat storage, service and sales business on Squire Pope Road which 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 the Oakley property on the Intracoastal Waterway is best known for its valued tenant, the local SERG The band’s Skull Creek Boathouse restaurant.

Oakley owned more than a dozen units in the Village at Wexford shopping center.

He owned a number of buildings lining New Orleans Road, a key commercial corridor on the southern end of the island. And he had offices around Hilton Head Hospital.

More recently, he righted the ship at an island institution in what may become his most lasting contribution to the local economy.

Oakley bet big on Palmetto Bay Marina, one of the oldest and most historic docks on the island that’s home to a circle of condos, restaurants and small businesses on Broad Creek. The piers had suffered heavy damage from Hurricane Matthew in 2016, and even more damage from the failure of the property that left it in ruins.

It took 18 months to negotiate the complex web of properties and property claims. And he spent millions more to repair and expand the wharf.

Betting on Hilton Head

Oakley died a week before his 92nd birthday was great news in Tennessee.

Former US senator and ambassador to China Jim Sasser spoke at his funeral.

This was not very noticed in Hilton Head.

But Oakley believed in Hilton Head, owned a home in Wexford and made the most of the local businesses he touched as a landlord – and excursions with friends aboard his 45-foot Grady-White center console with four 425 hp.

Oakley relied on an innate ability to assess business risk and personal character when buying property in the Southeast, often capitalizing on the fallout from the savings and loan failures of the 1980s and 1990.

“He always saw the promise in Hilton Head,” said Kuy Scott, who runs the Palmetto Bay marina. “He thought for years that maybe it had been slightly overlooked.”

A week before his death, Oakley was in Hilton Head to solve a major problem for local businesses that he felt so much part of: the lack of housing for the workforce. He was looking to buy land where affordable housing could be developed.

And those close to him say it could still happen.

Oakley “did 180 mph to the finish,” Scott said.

“He hadn’t had to work for 40 years, but at 91 he was here trying to solve the labor housing problem.”

‘To start all over’

Oakley was asked in a PBS interview by Becky Magura why it has always worked.

“When I was little, some kids had ice cream and I didn’t and I didn’t like it very much,” he said.

He characterized himself as stumbling upon opportunities and always having a partner who did the work.

He entered 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 spoke of big failures – in particular the Renegade Resort in Tennessee, where the main skiing attraction failed because it didn’t have enough elevation.

“You just got up and started all over again,” 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 partner with.

“I always try to get into a deal with people who are smarter than you and then think about it. I’ve noticed you’re lucky. I’ve always noticed the harder you work, the more You’re in luck.

“It was not just a question of money”

It was introduced to the Hilton Head market by longtime commercial realtors John Scott III and Spain Kelly.

“He was really smart,” said Scott, father of Kuy Scott and a 40-year-old friend of Oakley and his wife, J. Annette “JJ” Oakley. He worked with Oakley on local purchasing through his company MSK Commercial Services.

“He could measure things pretty quickly. He had the means and the ability to make things work. He had a special skill set. He could see things that others couldn’t 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 brings out the best in his associates, but he’s not an overbearing boss or owner.

“It was kind of like ‘if it ain’t broke, don’t fix it,'” Kaple said.

He said Oakley told him he lost more money not making a deal than he ever lost in deals. He always referred to his dealings as “trades”, even when it came to money.

Rob Jordan, a partner in the SERG Restaurant Group which is Hilton Head’s largest employer, said, “He wanted to see us succeed.

Jordan said Oakley didn’t like Hilton Head’s famous golf course or beaches.

“He loved people,” he said. “It wasn’t all about the money. It wasn’t all about ownership.

David Lauderdale can be contacted at LauderdaleColumn@gmail.com.