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Robert F. Chew (Proposition Joe Stewart)
Working out of an unassuming appliance store front, eastside narcotics kingpin Proposition Joe prefers peace to war and profit above all. When Avon Barksdale - his Westside rival - was imprisoned, Prop Joe managed to entice Stringer Bell - Barksdale's No. 2 - into an alliance. Bell opened up the lucrative Westside high rises in exchange for Prop Joe's better dope. Joe's drug connection is his greatest asset - Greek suppliers who come straight through the Baltimore port, eluding the wiretap investigation of port corruption. It's also led to his greatest triumph: the New Day Co-Op, a drug syndicate of Baltimore that puts product before territory by promoting peace and security for all the members, as well as access to Joe's cheap, potent supply of raw heroin and cocaine. A practical man, Joe is not above the need for violence when violence is required. In order to cement the deal with Bell, he helped to manipulate Omar into hunting down and shooting a New York enforcer, Brother Mouzone, brought in by Avon Barksdale to help maintain a grip on the towers. Such double-dealing is always achieved with discretion, and Prop Joe maintains a low profile that has kept him free and profitable for years. When New York dealers start making inroads into East Baltimore, Prop Joe sets up a double cross again, pitting pitting Omar against Marlo Stanfield in a plot to get Marlo to join the New Day Co-op to fend off the NY crew. He succeeds, but when the double cross backfires, Marlo's anger leaves Joe vulnerable.