JACKSON, Miss. – With powerfully haunting eyes and an enigmatic expression, “Portrait of Frederick,” an enslaved man painted circa 1840, stares out at visitors of the Mississippi Museum of Art.

A little further into the museum is Delia, a Black woman dressed in red and wearing a headscarf who bears a similarly unknowable expression. The pair of portraits are the only known preemancipation paintings of enslaved people in Mississippi.

Now, for the first time, they hang together for the public to see.

“I was mesmerized by the painting,” museum visitor Staci Williams said. “The colors, the expression. His humanity seemed to jump off of the page.”

The portraits evoke questions about who Frederick and Delia were, why they were painted and what went through their minds as their faces were captured stroke by stroke for generations to see.

“We don’t know, for example, if either of these people had the choice to sit for the portrait. We don’t know if they had the choice of what they were wearing when they were painted,” said Betsy Bradley, the Laurie Hearin McRee director of the museum. “They certainly weren’t allowed to own their own portrait.”

The museum bought “Portrait of Frederick” in partnership with the Crystal Bridges Museum of American Art in Bentonville, Arkansas. The museums will pass the portrait back and forth, each displaying it for several years at a time.

Bradley said purchasing the portrait brought up complicated feelings. Until emancipation freed him, Frederick was considered property. Now, more than 150 years later, his portrait is property, bought and sold to the highest bidder.

“If it enables us to have important conversations with each other about the human cost of slavery and why it mustn’t ever happen again, then having it in a public place can be meaningful,” Bradley said.

Since the 1860s, “Portrait of Frederick” has been displayed at Longwood, an antebellum mansion in Natchez, Mississippi, that belonged to the family of his enslavers. There, Frederick’s likeness was used to whitewash history.

According to research by the Neal Auction Company, which sold the painting to the Mississippi Museum of Art, tour guides in the 1970s informed the public that Frederick had grown up alongside his enslaver Haller Nutt, and the two were best friends. They claimed Nutt freed Frederick and referred to him by the belittling moniker “Uncle Frederick.”

In actuality, Frederick oversaw other slaves on the plantation. He collected data on field production, analyzed growing conditions and acted as a manager. His role was important, and he and his family may have received better living conditions as a result.

Frederick was about 70 when the Civil War ended. He took the surname Baker and became ordained. Prior to emancipation, Black people were not allowed to marry. Frederick married at least 69 couples after it became legal.

Less is known about Delia. Her portrait was painted between 1840 and 1849. She appears to be sewing, which leads some to believe she worked inside her enslavers’ home. Delia’s portrait was kept by the descendants of her enslavers until the Mississippi Museum of Art bought it 2019.

Both portraits are unique in that Frederick and Delia are the sole subjects of the works. Oftentimes, Black people were painted alongside white people, likely as a way of underscoring the white person’s wealth.

Frederick is dressed in regal garb — something he likely would not have worn in his everyday role on the plantation. Both are depicted in a three-quarters composition, which was used for dignified and important subjects.

Upon looking at “Portrait of Frederick,” Williams said she felt a surprising mixture of pride and sadness.

“I wonder about what he’s thinking,” Williams mused. “He doesn’t seem to give anything away.”