Charcoal portrait of Bill Anderson in jacket with top button closed, shirt, carvat, and a brimmed hat with a lone star on the upturned brim and embellished with an ostrich plume. Bill Anderson was a chief lieutenant under William C. Quantrill and earned the sobriquet "Bloody Bill." He later was a lieutenant under George Todd. He was part of the Lawrence massacre on August 21, 1863, and responsible for much of the Centralia, Missouri, massacre on September 27, 1864. He was killed October 26, 1864, near Orrick (Ray County), Missouri.