Robert was a Tuskegee Airman and flew a P-51 Mustang, and was an active participant in the U.S. civil rights movement. During the war, his wingman, Moe, often took credit for things that Robert did or that they dually accomplished together, and Robert's angst about this culminated at Moe's funeral, during which he blows the lid off of some of Moe's more embellished accomplishments.
Robert also lived in Alabama during the U.S. civil rights movement. He specifically recalled showing up late for a march because he forgot his raincoat, much to the indignation of his cohorts. He also had a grudge against Rosa Parks for "stealing his thunder", as he was sitting next to her on the bus and likewise refused to give up his seat. The bus driver was only offended by Rosa's, not his, unwillingness to move, however; also, he claims Malcolm X died owing him five dollars.
Robert describes himself as a "Civil Rights Legend." However in reality, Contributions to the struggles were quite minimal to barely anything at all. When describing his experiences during those times he shamelessly includes himself alongside several important figures during that period. Quite frankly he earned more animosity from Blacks then he did White people. He also says he's related to Jackie Robinson. According to him the Freeman is silent.
Robert (aka Mr. Bitches) is also a pathological and compulsive liar; he is also quite selfishly motivated. The Professor was handling his psychological treatment, in his absence Memory is talking to him, but frankly, without Captain Stern's force of personality Robert surely would be on a downward spiral again.
Robert has also been revealed to be extremely incompetent with money and finances, probably that's another reason why he is living and working at the Mansion with his grandsons.