Marion Barry has this painting in his office of him riding a horse, while wearing a cowboy hat. What are the circumstances behind its creation?

Marion Barry is a man who can appreciate a second act. Perhaps no artifact in the Wilson Building captures second chances better than the painting that hangs with pride of place in the Ward 8 councilmember’s office. That acrylic portrait of Barry, depicting the Mayor for Life on a horse with no name, is by D.C. artist Horace Crenshaw.

A resident of Fort Dupont, Crenshaw learned to paint while serving a 12-year sentence for manslaughter in a federal penitentiary in Butner, N.C. He shot a man in Northeast D.C. over a $150 craps debt. While in prison, Crenshaw learned he could draw and paint—well enough that his portraits of fellow inmates commanded a handsome value on the prison market. He was released in 1992.

“It’s been a few years,” muses Crenshaw, who doesn’t remember exactly when he made the painting. Some friends of Barry commissioned the portrait, he says, and he picked an equestrian pose because it struck him as the most energetic. He says he painted it from a photograph. The portrait shows a younger and hardier Barry riding horseback, brandishing a feathered cowboy hat as he rides under an open, star-filled sky. While Barry’s days as an equestrian may be behind him, Crenshaw is still an active portrait artist. “That’s all I know how to do,” he says.