Caldwell is a Burglary detective with the LAPD. He was possibly the partner of Cole Phelps during his time at the burglary desk, before Phelps' promotion to the Homicide department. Among his investigations, Caldwell was assigned, along with McManus, to investigate the SS Coolridge robbery. Caldwell deduced that the robbery was an inside job, and that the perpetrators were either dock workers or passengers on the ship. However, even after over six months of investigation, Caldwell failed to find any of the stolen supplies from the heist, or narrow down suspects.
Events of L.A. Noire
Caldwell appeared during the street crime Against the Odds. Phelps met Caldwell in front of a bookmakers, where he briefed Phelps of the situation. Caldwell received a tip that a bagman named Rampley was going into the bookmakers to collect money that he won in a fixed horse race. Caldwell stated that, while he did not care much about Rampley, but hoped that Rampley would lead the detectives back to his boss. He asked Phelps to attempt to tail Rampley back to his boss, which Phelps did so successfully. However, they opened fire on Phelps, and he killed both of them in a gunfight.
While Phelps worked alongside Roy Earle during his time on the Vice desk, they investigated a shooting at the 111 Club. The owner of the club, Eddie McGoldrick, who was killed alongside Bittleston and Bowe, fought alongside Cole Phelps in the Marines, during World War II. Phelps quickly found things that were stolen from the SS Coolridge, such as cigarettes and BAR's. Phelps quickly realized that his old unit was responsible for the robbery.
Phelps found Caldwell, who was investigating the heist. Caldwell assisted Phelps and Earle in the investigation, showing him the ship manifest listing of all of the stolen goods, and the list of all the passengers that were on the crew when the goods were stolen. Caldwell proceeded to the club to inspect the stolen supplies and to solve the case.
Street Crimes (Vice)
- The actor who provides the voice and likeness of Harold Caldwell is Brandon Keener, most famously known as the voice actor for Garrus Vakarian in the Mass Effect series. Also, he is the voice actor for American Sniper in Company of Heroes.
- Similar to Roy Earle, Herschel Biggs, Rusty Galloway and Stefan Bekowsky, Caldwell is a smoker. As seen in Manifest Destiny when Phelps and Earle are talking to him.
- When asking Roy Earle for assistance when inside the Hollywood Police Station, he'll mention that Caldwell and Phelps used to work together. In addition, upon speaking to Caldwell, a friendly atmosphere surrounds the two, suggesting likely partnership. The two have "catching up" to do if the player uses the Talk button when near him, according to Caldwell. All of this further hints at the fact that they may have been partners during the burglary desk.
- Up to three Caldwells can spawn in the Wilshire Police Station, Central Police Station and the Hollywood Police Station but with different outfits. Oddly, using the "Talk" button only derives rude comments (e.g., "Why don't you go and polish your war medal and leave me alone?")
- When he has his jacket on, his badge number is 1432, the same number as Ray Pinker. But when he doesn't have his jacket on, the number is 3154, the same badge number of the photographer Roger Becket. The same thing happens with Joseph Hobbes and William Tilden.
- His badge number says (only when he doesn't have his jacket on) photographer instead of detective.
- Although there is speculation Caldwell was once the partner of Cole Phelps, during the street crime "Against The Odds" Phelps introduces himself to Caldwell as if they had never before met.
- His name strongly suggests he is of English descent.