The King of King Street: How One Power Professional Built His Southeast Empire

It’s hard to imagine Charleston now, with its upscale boutique hotels, trendy eateries, hipster-friendly vibe and international accolades, as anything less than the sophisticated city that today routinely tops Travel + Leisure lists.

But there was a time, not that long ago, when the antebellum architecture and cobblestone streets were nothing more than decaying reminders of the city’s Golden Age, now lost to memory. It was during this time that Virginia and Warren J. “Red” Bennett provided for their six children any way they could: Red shined shoes near Marion Square, before finding some small success in later years as a business owner. Virginia worked odd jobs on King Street. But soon, a five-star luxury hotel will occupy those same streets. Their name will adorn the front.

The Hotel Bennett is just the latest project of Holy City Hospitality, the organization founded by their son Michael, that operates hotels and restaurants from Charleston through to Savannah, all the way down to the Florida Keys and all the way west to Montana.

“When I was growing up in the ’60s and early ’70s, there were not any opportunities in this community,” said Michael. “If your father was a doctor, you might become a doctor. If your father was a lawyer you might become a lawyer. My father owned a junkyard and a truck repair shop.”

Although he deeply respected what his father did to put six children through school and college, he knew that he was destined for bigger things. What those bigger things were exactly became a little clearer during a gap-year stint on a cruise ship that introduced him to the lavish oceanside hotels and fine restaurants at port towns from Martha’s Vineyard to the Chesapeake Bay.

When he returned to Charleston, he came back to a city that was ready for reinvention. Under Mayor Joe Riley, the Holy City was just beginning to regain its standing, with the birth of Spoleto and with a renewed focus on preserving and restoring historic buildings.

“Charleston was totally unrenovated then, but you could smell in the air that things were changing,” he said. After selling a bike and moped rental business he’d been running, Michael threw himself into restoring Charleston. “I had an insatiable appetite for these old buildings.”

“There are so many great restaurants and great chefs. Savannah’s moving in that direction. It’s very competitive but it’s a great industry.”

With a building boom going on around him (thanks, in part, to Reagan-era tax incentives that brought what Michael calls “the first big wave of Yankee money coming down,”) he began buying and restoring properties for $20-40,000 that now regularly go for millions.

But one property in particular presented the chance to do something different. The old Chicco Apartments on John and Meeting St. occupied a spot right in the middle of Charleston’s deepest blight. But in its dust and cobwebs Michael saw potential. He bought it just after Hugo rolled through town and turned the Chicco into a Hampton Inn. His career in hospitality had begun.

“It was the only occupied building for blocks; everything else was blighted,” he said. “So I thought we should put in a restaurant up there, so guests would see a restaurant next door and think there’s more up that way.”

That restaurant, after a brief and not overly profitable stint as a Houlihan’s franchise, became 39 Rue de Jean. Holy City Hospitality was officially in the restaurant business. What followed was a slow growth along King Street, with the company opening restaurants strictly to support the hotel business. As luck would have it, Charleston’s culinary profile skyrocketed around that time and 39 was joined by several other HCH restaurants, from Vincent Chicco’s to Virginia’s on King, named for Michael’s mother.

As Michael’s empire grew beyond Charleston, he formed Bennett Hospitality. His first stop was Savannah, where he built another Hampton Inn and an Embassy Suites before transplanting the Rue de Jean concept to the fertile soil of Savannah’s growing foodie scene.

“The restaurant business, my God, is so bloody hard… There are so many great restaurants and great chefs,” he said. “Savannah’s moving in that direction. It’s very competitive but it’s a great industry.”

While he remains hands off when it comes to operations, he speaks passionately of the concept and design for each project he touches. Rue de Jean, for example, was molded in the style of the classic brasserie, with timeless motifs and classical materials inspired by such French eateries as New York City’s Balthazar.

“I love design work,” he said. “I can’t draw, but I like creating pretty things.”

And through Holy City Hospitality and Bennett Hospitality, he’s created many pretty things. His restaurants have not only capitalized on the south’s growing profile among the nation’s foodies, they have in many ways defined it. He’s put his stamp on the entire region, not just the city that he calls home. It’s a long road from working on a cruise ship, but it’s one that has had a tremendous impact on every city at which it arrived.

If nothing else, as Michael quipped, “It beats working at the truck repair shop.”

For more information on Bennett's restaurants in Savannah & Charleston, go to holycityhospitality.comsubscribe now or pick up the August/September issue of South magazine.