The Chinqua-Penn Plantation had seen better days. Built a century ago in Rockingham County, the 27-room private manor home was filled with stunning artwork and furnishings from the extensive travels of owners Thomas Jefferson Penn and his wife, Beatrice “Betsy” Schoellkopf Penn. After Betsy died in 1965, the estate, which is listed on the National Register of Historic Places, changed hands several times. By 2012, its then-owner, facing bankruptcy, was forced to sell the contents in order to pay off creditors.

Leland Little, president of Leland Little Auctions in Hillsborough, had conducted countless estate auctions in his years in the business, but the Chinqua-Penn Plantation was special for him. A voracious student of North Carolina history, he was well-versed in the significance of this grand mansion and of the Penns’ many cultural and philanthropic contributions to the region. As he surveyed and documented the items in the home with the trained objectivity of a professional auctioneer, Little’s eye stopped at the portrait of Betsy Penn hanging on a wall in the dining room. “It belonged there,” he says. “It ached our team’s collective heart to take it down and carry it out of the house.”

Leland Little curates an experience that connects people from across the globe with the legacies of artisans and craftspeople from North Carolina. photograph by Jerry Wolford & Scott Muthersbaugh

In addition to getting the best prices for the art work that he sells, Leland Little also enjoys returning rare pieces — like the portrait of Betsy Penn — to their homes of origin. Photography courtesy of Leland Little Auctions

Fortunately, this story has a happy ending. Years later, Chinqua-Penn was bought by a new owner, who asked Little to help track down some of the items from that earlier auction, including the Betsy Penn portrait. Today, the painting once again hangs in its original spot in the dining room.

For Little, the full-circle saga of that portrait is a beautiful example of how North Carolina’s rich cultural conversation continues to be passed down as new generations discover and repurpose previously owned treasures. It’s why Little and his team have reimagined the auction experience to provide people from all walks of life with opportunities to understand and appreciate the legacy of artists, artisans, craftspeople, and collectors from across our state. Like many auction houses in the Internet era, Leland Little now conducts its sales online, which allows people from Murphy to Manteo to Madrid to bid in real time.

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On a weekday afternoon, the company’s headquarters just off NC Highway 86 is bursting with activity. The 40,000-square-foot complex, designed by Chapel Hill architect Richard Gurlitz, includes an event space for preview receptions and community gatherings, gallery walls filled with artwork, an entire bay for classic and collector cars, and a fine-wine retail shop. Specialists in numerous areas of expertise — from rare coins, jewelry, and Asian arts to photography, fine art, and historical documents — are busy researching and cataloguing the steady stream of items slated for future auctions. With an international following and a reputation as one of the most trusted auction houses in the South, Leland Little offers up items that have fetched as much as hundreds of thousands of dollars.

But for Little, the enterprise is about more than just getting top dollar for his clients. “Part of our mission is to foster artistic and cultural appreciation and continuity across generations,” he says. “For example, our sporting arts department specializes in hand-carved Southern decoys that were made by hunters and fishermen in eastern North Carolina to put food on the table. Today, they represent a coastal way of life that has disappeared, and admiration for the craft has skyrocketed.” Those little decoys, he says, have now become coveted collectors’ items.

Little is especially proud to offer pieces by artists whose works have been overlooked or undervalued. Recently, two paintings by the late North Carolina-born athlete and artist Ernie Barnes were part of a Leland Little auction. Barnes, born near Durham’s Hayti district during the Jim Crow era, created colorful works that depict the fluid physicality and exuberance of some of the people in his African American community. His most famous work, The Sugar Shack, was featured in the 1970s sitcom Good Times and on the cover of an album by the late R&B singer Marvin Gaye; today, one version of that piece is owned by comedian Eddie Murphy.

After years of being undervalued, paintings by artist Ernie Barnes now fetch six figures among collectors of fine art. In 2023, Leland Little Auctions sold Barnes’s 1974 piece Last Hurdle for $150,000. Photography courtesy of Leland Little Auctions

According to Barnes’s memoir, From Pads to Palette, he visited the North Carolina Museum of Art as a teenager and asked a docent where he might find “paintings by Negro artists.” Barnes was told, “Your people don’t express themselves that way.” Little is pleased to report that things have changed dramatically at the museum since those days. “One of his paintings that we offered for auction, Last Hurdle,” Little says, “was purchased by the North Carolina Museum of Art for its permanent collection.”

Little’s role in the art-world ecosystem can’t be overstated, says Larry Wheeler, director emeritus of the NC Museum of Art. “Leland has become an extraordinary resource, not only to our state and our region but also nationwide and worldwide,” Wheeler says. “He’s opened people’s eyes to exciting contemporary art and design, as well as to artists like Ernie Barnes. Leland gets strong prices for those works, and that leads to stronger prices when those items come up for resale. What he brings to market is first-rate.”

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Little got into the auction business by accident. In the 1980s, he was a college student trying to earn a few extra bucks when he heard that an auctioneer needed some extra muscle at an upcoming event. Little arrived at the estate before dawn to help haul furniture out of the home and arrange it on the lawn.

As the sun came up and the auction got underway, the young college student became captivated by the crackling energy of the moment, the singsong gallop of the auctioneer’s voice, and the multigenerational mix of people who showed up, from seasoned collectors looking for deals to children chasing each other around the yard. By the end of the day, Little had been bitten hard by the auction bug, which he saw as part community gathering, part treasure hunt, and part eye-opening education about what is valued and why.

In 2023, the Hillsborough auction house helped place a mahogany wardrobe designed by 19th-century craftsman Thomas Day back into his original workshop in Caswell County. Photography courtesy of Leland Little Auctions

Today, Little and his team view their collective role in the art and design world as stewards and shepherds, making sure that precious and significant objects will be treasured for decades to come. This means that there are times ­— such as with the Betsy Penn portrait — when Little can track down something sold at auction and ask the owner to resell it for the greater good.

That happened again last year, when the state’s General Assembly approved funding to designate as a historic site the Caswell County workshop of 19th-century free Black craftsman and furniture maker Thomas Day. Little was approached by the NC Department of Natural and Cultural Resources, which was interested in a mahogany wardrobe, signed by Day, that Little had auctioned off years before. He contacted the buyer, who agreed to sell it to the state. And now, thanks to an auctioneer with a deep appreciation for North Carolina art and culture, that wardrobe once again resides in Day’s Union Tavern workshop in Milton, back home from a long journey that began more than 150 years ago.

Leland Little Auctions
620 Cornerstone Court
Hillsborough, NC 27278
(919) 644-1243
lelandlittle.com