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- "You lose something, Mac?"
- ―Carraway confronting Kelso
Nothing is known about Carraway's early life.
Hiring by Monroe
When Jack Kelso was approached by Elsa Lichtmann who rejected a $20,000 insurance settlement for the death of Lou Buchwalter, Elsa expressed her suspicions that Elysian Fields Development was attempting to cover up something that was more than just an accident. Kelso's boss Curtis Benson, however, pressured Kelso, telling him to make Elsa accept the settlement and close the matter. Kelso began his investigation at the housing development site, the site of Buchwalter's death, where he discovered that the houses were made from inferior and unreliable materials and later found a connection to the Suburban Redevelopment Fund. In shock, Kelso also discovered his own boss, Benson, was involved along with Leland Monroe, the Mayor, Police Chief, District Attorney and other influential figures.
Learning about Kelso's investigation and worried that he might be an obstacle to his criminal empire and the Suburban Redevelopment Fund, Monroe hired hitman Don Carraway and his henchmen to find and kidnap Kelso after which they phone Monroe for further instructions.
After realizing that Kelso wll be at the Elysian Fields Development site, Carraway and his henchmen Garfield Henderson and Walter Tyler entered the Elysian Fields site where they ambushed Kelso. Suddenly, Kelso starts a fistfight by punching down Carraway. However, Kelso ultimately loses the brawl and the hitmen throw Kelso into the trunk of their car. Still keeping Kelso in trunk of their car, Carraway phoned Monroe and asked him about what they do about Kelso and Elsa. Afterwards, the three hitmen were driving off when Kelso escapes from the trunk. Realizing that they would go after Elsa next, Kelso managed to shake off Carraway and his men and escaped with a stolen car, driving off to Elsa's hotel.
- "Know why I plumped for the Caddy? The extra trunk space."
- ―Don Carraway making an insinuation about Kelso's weight.
After being treated for his injuries, Kelso went to the Land Registry Office at The Hall of Records. Using the official records of the SRF, Kelso found the names of the main directors and shareholders, including former warmate Courtney Sheldon's. Upon seeing the increased insurance value, Kelso deduced that the Monroe's plan was to burn the phony houses to cash in grand insurance money.
However, Carroway along with Henderson, Tyler and another unidentified gangster also arrive at the hall after learning that Kelso is there. After a brief exchange of dialogue between Kelso and Carraway, a gunfight follows. Kelso exacts revenge for his earlier beating by shooting and killing Carraway and his men.
- Even if Kelso kills Carraway (and his men) in "House of Sticks", Carraway and his men still appear in "A Polite Invitation" where they are killed by Kelso, meaning that their (optional) deaths in "House of Sticks" are non-canonical.