Among his many acquaintances, Rollins had a lifelong friendship with artist and politician George Caleb Bingham. Bingham painted numerous portraits of Rollins family members, including several of Rollins himself. Rollins gave Bingham a boost early in his career by getting several people in Columbia to have him paint their portraits. He later helped Bingham get a commission to do portraits of Thomas Jefferson and George Washington for the Missouri State Capitol,Christ-Janer, 33-34. These paintings were destroyed when the capitol burned in 1911. and he helped finance printings of Bingham's General Order No. 11. Late in Bingham's life, Rollins helped him get a position as the University of Missouri's first art professor.Nagel, 141.
