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 head scarf who bears a similarly unknowable expression. The pair of portraits are the only known pre-emancipation paintings of enslaved people in Mississippi. Now, for the first time, they hang together for the public to see. 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 MMA. "They certainly weren't allowed to own their own portrait.” MMA 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.