|Family||Pinky Gauthier (cousin)|
|Missions|| Dishonorable Fight|
|Voice Actor||John LaVelle|
- "It takes more than victory to become a champion. It takes breeding, and nepotism, and snobbery!"
- — Derby
Derby has blond hair and prominently black eyebrows. Like all the Preppies, he wears Aquaberry clothing, a sweater vest in the summer and a long sweater in the winter. He also wears gray slacks and a dark gray vintage hunter's cap in the wintertime. He's a medium-sized student, and is slightly shorter than his friend and bodyguard Bif Taylor.
Derby, which is pronounced "Darby" like the English city, is the most 'blue blood' of the entire Preppies clique. His family is one of the main benefactors of the school already, and the Preppies fraternity house is even named "Harrington House". Although not much is known about his family life, it can be deduced that they are involved in the oil business. Billboards for "Harrington Oil" can be seen at the Carnival's go-kart track. The Harringtons may also own stock in Aquaberry; Aquaberry brand sweaters are acceptable by the Bullworth Academy dress code, and Derby can be seen on posters in the Aquaberry outlet store, modelling the clothes. He is apparently a Republican, as he insults Bif by calling him a "filthy Democrat".
Derby is arrogant, snobbish and mean-spirited even by Preppy standards. He berates Bif after he loses a boxing match against Jimmy. He's also a master manipulator, however, unlike Gary he has no interest in running the school. Whereas the other clique leaders apparently come to like Jimmy, Derby never loses his contemptuous manner, nor does he ever treat Jimmy with respect unless threatened or forced to. Although betrothed to his cousin, Pinky, he no-shows a date with her. Derby apparently has had an affair with his nanny in his past, but was caught and beaten for it by his father.
Of all the Preppies, Derby seems to take the most pride in his family's wealth, possibly to the point of egomania (if he loses a fight, he declares the result to be a draw), and uses money to solve everything. Most of his insults involve demeaning the economical status of his opponent. When chasing someone, he warns his opponent that he can "hire people to hunt him/her down" and when out of breath, he claims that he could just hire someone to beat his opponent up for him.
According to Justin, Derby claimed to be his best friend.
Role in game
Derby makes his first appearance during This Is Your School, when Jimmy sees him in the Cafeteria flirting with Pinky and conversing with Tad. Derby later appears during Jimmy's fight against Russell in The Hole, accompanied by Pinky and Bryce.
During Chapter 2, Derby remains behind the scenes until the very end. After Jimmy has beaten Bif in a boxing match, Derby leaves the bar in the second floor of the gym to confront Jimmy. Jimmy chases him back to the bar, where Derby attempts to hide behind his friends. Jimmy can barricade the doors to prevent the other Preppies from helping Derby, but he doesn't have to do this to win the fight.
Derby continues to be a manipulator even after losing the fight, however. When Jimmy helps the Greasers get revenge on Gord for dating Lola, Derby manipulates Jimmy into spraypainting graffiti in New Coventry, which turns the Greasers against him.
During Chapter 5, Derby is the one who manages to convince Jimmy that spraying graffiti on the roof of Town Hall is a good idea. Later in that chapter, the Preppies gym is vandalized, and Derby refuses to consider that anyone besides the Greasers were responsible. Jimmy manages to get photographic proof that the Townies were the real perpetrators, but Derby refuses to look at the pictures.
Finally, during the school-wide riot, Jimmy finds Derby wearing a smoking jacket while hiding out in Harrington House, seeming to be entertained by the riot.
Strangely, he appears after the mission Final Showdown, applauding Jimmy with many other students, which seems to be well out of character for him.
Meeting Derby During Free Roam
- After you have taken the photo of the burning trophies in the mission Preppies Vandalized, go back to the boxing gym. Approach Derby and Bif from the right side of the gym, while you are aiming with your camera. Get close enough to them and Derby will insult you. Bif will probably run towards you. Do not attack him or the mission will end. After you leave Bif behind, go back to Derby. Keep your camera out until he is close enough to you. He will insult you, but he will also fight if provoked. Jimmy also has the power to make Derby run away if he has completed his English course, and he will run into the back alley of the Boxing Gym. If you turn around and go into the alleyway the other way you can go right up to Derby and interact with him.
- Internal game data lists Derby's name as "Darby", suggesting that he was originally given this name during development
|2nd In Command|
|Bryce Montrose · Chad Morris · Gord Vendome · Justin Vandervelde|
|Harrington House · Old Bullworth Vale|