Orlando Haddick is a long-time friend of Vincent Brooks' from the video game, Catherine. In addition to being a friend of Vincent's, he is also a co-worker of Vincent's. He works as a software engineer. He claims that it was coincidence as it was the only hiring when he was looking for a job. Though a good friend, he is not seen as very reliable with money, and easily duped by scams and tricks and get-rich-quick schemes. He often hangs out at the Stray Sheep bar with Vincent, Tobias "Toby" Nebbins, and Jonathon Ariga. His drink of choice is beer.
Orlando knew Vincent ever since childhood. As children, Vincent would often help Orlando with his problems at the time. Orlando was once married young, but later divorced. He was initially happy with his wife, until he lost all his money in a failed business. He is adamant that she left him for it and felt betrayed. Due to this "betrayal", he filed for a divorce. This stemmed a grudge against his ex-wife.
Due to being married once, Orlando helps Vincent with his current relationship with Katherine McBride. He often gives Vincent advice and helps Vincent with what he should do about his recent affairs with Catherine.
Orlando later starts showing up in the Nightmares as the "Sheep with Red Hat". His boss stage is his ex-wife demanding to know why he left her. Later in the nightmares, he tells Vincent that his wife tried to get back together with him, but rather took this as her mocking him. Orlando is baffled as to why he was thrown into the nightmares as he was the one who felt betrayed. However, his own selfishness is preventing him from getting back to together with his wife.
In the Katherine True Ending, he is seen at Vincent's and Katherine's wedding with his ex-wife, deciding to give things another chance.