On the episode of The Celebrity Apprentice that aired on NBC March 6, host Donald Trump asked the two competing teams, named Empresario and Hydra, to sell art for their chosen charity organizations in collaboration with New York's Moti Hasson Gallery. After looking at reproductions of works by the gallery’s artists, the teams chose David Kramer and Shirley Shor. Empresario thought the lower-priced drawings and paintings by Kramer would be more likely to sell, while Hydra went for a higher price point with new-media artist Shor.

Shor won out, with Hydra selling almost $170,000 of her work, largely due to project manager Piers Morgan's connections with wealthy friends willing to help him out for a good cause, the Intrepid Fallen Heroes Fund, a nonprofit that provides grants to the families of fallen U.S. servicemen. Hydra was only able to sell $7,000 worth of Kramer’s art, with Donald Trump, Jr. chastising team member Stephen Baldwin for not persuading his New York friends to buy more of Kramer's work.