McCaskill is a former lieutenant of the now deceased Don James "the Hammer" O'Malley. He became new Don of his own Mob family and also Capo of the city after the forced retreat of the former Don of Milwaukee. Since the loss of Don Jimmy "Tools" O'Toole of Chicago during the Bug City events he also was promoted Capo of the bigger city at the great lakes.
After the death of James O'Malley in January 1, 2058 he was sent to Seattle by the Commissione to clear up the mess after the so-called "New Year Shot", find the killer of the deceased Mob boss and install a new Capo to lead the three Mob families of Emerald City. Also he found some evidence, that Don Maurice "the Butcher" Bigio had ordered the assassination of the former Capo O'Malley he couldn't do anything other than promote Don Bigio as new Capo of the city.
In the beginning 2070th he still holds the position as a Capo of both Cities: Chicago and Milwaukee. As an old friend of her father's family he is a great supporter of Dona Rowena O'Malley, the daughter of James O'Malley and new Capa of Seattle.
In 2072 he has become a bitter man. His control over the Feral City of Chicago hasn't improved very much. Instead he's fighting a struggling war about the business opportunities there against the Greek Mob from Detroit, which moved in after the Crash 2.0 and has taken some parts of the Chicago underworld for himself, as well as against Capo Jules MacAvoy, a local mobster from the former O'Toole Family, who has started his own crime outfit.
McCaskill's famed chief lieutenant was the twisted physical adept Edward Milhouse, also known as "Eggs Milwaukee". After Eggs' death during the Seattle events of '58/'59 his new chief lieutenant became a heavily cybered mundane, known only under the street name "Frontline".
- Feral Cities - 4th Edition location sourcebook
- Mob War! - 2nd Edition campaign book
- Runner Havens - 4th Edition location sourcebook
- Underworld Sourcebook - 2nd Edition sourcebook
- Vice - 4th Edition sourcebook