Orland eventually becomes the leader of the Keepers in Thief: Deadly Shadows. His leadership quickly proves officious, bureaucratic, and secretive, and Garrett learns to dislike him. He first appeared in Thief II: The Metal Age, albeit voiced by a different actor. He appears quite pedantic about the Keeper Order's rules and takes his position as First Keeper very seriously. He can't be praised with huge support from the rest of the Keepers, as some even suspect him of following personal interests.
Garrett and Orland seem to know each other very well. Orland doesn't seem to trust Garrett at all, but it is more likely he is envious of his skills. In various situations Orland puts serious obstacles in the master thief's way, but at the end of Deadly Shadows, he realizes that Garrett is not a threat.