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Dennis Quaintance’s eyes light up when he comes to the intersection of Green Valley Road and Benjamin Parkway.
“In 1980, I was right here at this stoplight with my wife Nancy on the back of my old BMW R60 motorcycle,” Quaintance says. “We were just dating then. She was finishing up her degree in hotel management. And I pointed right over there—there were just trees there then—and I said, ‘That’s it…that’s where we should build our first hotel.’ About 16 years later, we did.”
Did it happen just that way? Could it have been that simple? Was there a straight line from that motorcycle ride to the creation of the O. Henry Hotel, now a Greensboro landmark? It’s a little more complicated, Quantance admits. But it’s a good story. And good stories are important.


“I’m romantic,” Quaintance told The Thread last week. “I believe stories are the fabric of society. We sort of, as human beings, live on stories. And if we fail to create them as a community, we’re failing to create the glue that holds us together.”
That’s why Quaintance and his partner Mike Weaver didn’t, like the Hiltons or the Marriotts, put their own names on the hotel they opened in 1998. They wanted to build something, as they say, of and for Greensboro. So they reached back into the city’s past—to perhaps Greensboro’s greatest native storyteller and the grand hotel, now largely forgotten, that once carried his name.
William Sydney Porter was born in Greensboro in 1862. He spent his early, formative years in the city, studying first at his Aunt Lina’s schoolhouse and then at Lindsey Street High School. At 19, he became a licensed pharmacist, working at his uncle’s drug store, observing the customers and making sketches of them.
But it wasn’t until his thirties and a stint in a federal penitentiary for embezzlement that Porter, now under the pen name “O.Henry,” began focusing on the short stories that would define his career. With tales like “The Gift of the Magi”, and “Mammon and the Archer,” O.Henry crafted sentimental stories centered on the struggles of everyday people. They made him one of the nation’s most famous storytellers.
As the roaring 1920s approached, Greensboro struggled to interest outside developers in building a new, modern hotel. Residents stepped up, deciding to do it themselves. Funding it with community stock subscriptions, they built an impressive 300-room structure at the southwest corner of Bellemeade and North Elm Streets. They named it The O. Henry—an honor he would have appreciated as a man who lived most of his itinerant, Bohemian life in hotels.
O.Henry was more than the hotel’s namesake. His work and image were woven into the very construction and design of the building. The world of his stories lent it an urban romance.
“They have things from his childhood and manuscripts, they’re really trying to spin a connection to an imagination that’s well outside of Greensboro,” said Glenn Perkins, curator of community history at the Greensboro History Museum. “A lot of his stories are New York City stories about urban life, but there is a desire in branding the hotel to associate with that.”
That decision paid off quickly. Within six weeks, the eight-story hotel was fully booked, developing a reputation as one of the finest stays in the region. Patrons marveled at its majestic lobby, were pampered in its barber shop and hair salon, and danced at grand soirees held in its ballroom. Its second floor included a library honoring O.Henry, and illustrations from his works were included across the hotel, its common spaces and guest rooms. For years, local radio station WBIG operated out of the building, further cementing its status as a local institution both of and for Greensboro.
The hotel hosted Scott and Zelda Fitzgerald in the 1920s and big band stars like Guy Lombardo, Jan Garber, and Vaughn Monroe in the 1940s. But not everyone was welcome. Due to segregation, Black residents and famous travelers alike were barred, instead finding refuge in historic local sites like the Magnolia House.
“In many ways, they model this Southern segregated society,” Perkins said of the era’s hotels. “In their architecture and in what goes on within they are projecting how society is supposed to operate in a way.”
The O.Henry was still in its heyday in 1942 when a postcard depicting the hotel was used to reach out to a Miss Albertine Lefer as she was attending Wake Forest College. “Hope school agrees with you and I’m planning on seeing you soon,” the sender wrote.

But the good times couldn’t last.
By the late 1960s, the city’s downtown began to decline. Less opulent but more affordable hotels and economy motels pulled visitors from the O.Henry. Some accounts suggest the hotel was damaged in a fire and was never fully restored to its former glory.
By the mid-1970s, the hotel, now under new management, closed. In 1979, the building was razed and a parking deck was later constructed where the local landmark once stood.
Quaintance only saw the original O. Henry a few times. By then, he said, it was infamous as a mostly empty shell of its former self where police were often called to deal with guests who had overdosed. That reputation—like that of O. Henry drinking himself to death his last few years—lingered.
“There were some people who said we shouldn’t name the new hotel the O. Henry because of those memories, those associations,” Quaintance said. “We didn’t listen.”
Instead, Quaintance and Weaver built a new grand hotel in tribute—taking inspiration from the old downtown landmark’s colors and design scheme, its first-floor stone arches, and even the understated black and white tile in its bathrooms. Today, O. Henry’s portrait hangs in the large social lobby of the new hotel just as it did in the original, the text of his “Gift of the Magi” artfully etched on the walls above guests taking afternoon tea.
Quaintance has a trove of historical gems from the original O. Henry Hotel—plans, bricks, demitasse spoons, menus from elaborate holiday dinners. But one of his favorite artifacts is a copy of the dedication speech given by C. Alphonso Smith, prominent scholar and friend of O. Henry, when the hotel opened in July of 1919.
“In your behalf, therefore, and speaking for you, I dedicate this hotel,” Smith told a banquet of original community stockholders. “I dedicate it to the growth and prosperity of Greensboro. I dedicate it to the comfort and happiness of all those who may in after years find shelter and harborage here. I dedicate it in pride and gratitude to the memory of him whom we loved living and whom we honor dead. May his spirit in all the plentitude of his kindliness and sympathy and fellowship abide forever here. And may this hostelry, mindful of its dowry, be worthy of its heritage.”
That’s a dedication worth carrying on in spirit, Quaintance said, and he’s happy to be a part of it.
“You have to honor that history even as you make new memories for people in a place like this,” Quaintance said. “You have to continue the story.”
Joe Killian is The Assembly’s Greensboro editor. He covered cops, courts, government and politics at Greensboro’s daily paper, The News & Record, for a decade. He joined us from NC Newsline in Raleigh, where he was senior investigative reporter.