Courtney Sheldon is a veteran of World War II and was present as Sugarloaf Hill with Cole Phelps and Jack Kelso. After his time in the war he returns to Los Angeles and becomes a medical student. He becomes a pupil of Doctor Harlan Fontaine and gets involved in the shadier side of Los Angeles.
Courtney shows up in the first newspaper film clip at the beginning of the game. He continues to play a role in the newspaper clips until he is eventually interrogated by Cole Phelps. From that point on he plays a major role in the game's plot.
Sheldon is played by Chad Todhunter.
Courtney Sheldon was a medic during his time in Okinawa. He is first seen running into oncoming fire and putting a screaming rifleman "out of his misery." Phelps then questions Sheldon's motivations, but commends him on being brave enough to run into enemy fire.
After the incident in the cave Phelps gives Sheldon the order to kill all of the burning Japanese patients. Sheldon refuses to and shoots Phelps in the back.
S.S. Coolridge Heist
When Courtney Sheldon, Jack Kelso and the rest of their troop are travelling home on the S.S. Coolridge he mentions that they should steal all of the army surplus morphine so they can sell it and have some of the bright future that they were fighting for. It is later found out that all of the troop aside from Jack Kelso took part in the robbery. They wound up selling the majority of the morphine to Mickey Cohen.
After some time, Cohen starts demanding more and more morphine from Sheldon at which point Sheldon decides to break off his ties with the mobster. Sheldon enlists Jack Kelso's help to have a meet up and end the relationship between Sheldon and Cohen. Surprisingly it works and Sheldon gets away from the mob business.
When Cole Phelps is investigating the heist at the S.S. Coolridge, Sheldon requests to speak to Phelps and comes away with no evidence of being involved in the heist.
When Sheldon returned to LA he enrolled in medical school. After a lecture by Harlan Fontaine, Sheldon approaches him and asks if he could help one of his veteran friends (Ira Hogeboom). Fontaine takes Courtney under his wing and helps him break into the medical world.
Sheldon later tells Fontaine about the Coolridge heist and Fontaine offers to buy the rest of the morphine from Sheldon and the veterans holding it so that they won't have to deal with mobsters any more. He also says that he'll use the money he makes with the morphine to invest in new homes for GI's.
Suburban Redevelopment Fund
Courtney Sheldon's "investment" in the Suburban Redevelopment Fund nets him a name on the list of managers for the company. When Jack Kelso is investigating the fund he sees Sheldon's name on the list of registers managers and questions him about it. Sheldon says he had no idea that he was part of the company and tells Kelso all about the morphine deal. When Sheldon confronts Dr. Fontaine about the Suburban Redevelopment Fund he is killed by Fontaine and his body is discarded to make it seem like it was a suicide.