Richard Harrow (played by Jack Huston) was a disfigured war veteran, criminal, and friend of the now deceased Jimmy Darmody. He acted as Darmody's bodyguard and bootlegging partner. Richard Harrow is a seemingly calm but deeply troubled and ultimately tragic character. He is not just surrounded by death but finds himself useful chiefly as an instrument of death.
Harrow was a marksman in the US Army during World War I. A war injury caused substantial damage to the left side of his face; he lost his eye, most of his cheek bone, the left half of his upper jaw and endured heavy scarring. In order to enter society with the least amount of distress, Harrow covers his scars with a tin plate that was molded to his face and painted to match his skin tone.
After the war, Harrow returned home to Wisconsin where his twin sister, Emma, provided care for him as his wounds healed. He had a very close relationship with his sister growing up, but found it difficult to reconnect with her after being exposed to the horrors of war. Soon after he was well enough to care for himself, Harrow left to live in Chicago. It is there, in an army hospital, where he meets Jimmy Darmody. After feeling an instant kinship through their shared war experiences, Jimmy invites Harrow to stay with him to become a part of his bootlegging crew. His duties generally include keeping guard while Jimmy negotiates deals, delivering liquor orders and being a hitman when situations call for it.
Harrow keeps a scrapbook of pictures found in magazines and newspapers of family, sweethearts and houses. He alludes to wanting a family of his own, but has spoken of how difficult it is to connect with another human being on a deeper level due to his injuries.