As one of Baltimore's most notorious stick-up artists, Omar Little brings another element to the game: the hunt. With his long duster, battle armor and the sweep of his shotgun, he adds an additional element of risk for Baltimore's dealers. Uncomfortable with profanity and careful to rob only dealers and others in the game who can have no complaint to police, Omar shows particular pride when taking off the stronger organizations - though that pride has cost him.
After robbing a Barksdale stash house with two confederates - one his lover, Brandon, and another gunman named Bailey. He soon found himself hunted ruthlessly. Bailey was caught and killed first, followed by Brandon, who was himself tortured in an unsuccessful attempt to make him reveal Omar's whereabouts. In retaliation, Omar took the battle to the Barksdale organization, ambushing the hitters Wee-Bey and Stinkum, killing the latter and wounding the former. Subsequently, he made a point of testifying - in fact, perjuring himself - in a campaign to give a third Barksdale gunman, Bird, a life-sentence in a court trial. Manipulated by Prop Joe into ambushing Brother Mouzone - a gunsel brought down from New York to hold Barksdale territory and make an alliance between Stringer Bell and Joe problematic - Omar realized he'd been used after wounding Mouzone and so let the man live. Mouzone, after working his way back to Omar, learned the story and the two paired up briefly to successfully assassinate Stringer Bell, bringing Omar's campaign of retribution to an end.
Moving on to other targets in the drug world, Omar gets caught in a web of framing and retribution with Proposition Joe and Marlo Stanfield. When he finally pulls off a double-crossing heist, further alienating the two dealers, Omar takes the money and runs. But Marlo remains determined to smoke him out.