Character's Role: Easily the most diplomatic of the drug lords, Joseph "Proposition Joe" Stewart is the head of all east-side drug dealing for most of the series and usually manages the heroine shipments (through the "Greeks") for all of Baltimore. He acquired his moniker from his trademark phrase "I've got a proposition for you," and he is frequently seen making side deals with Omar Little, police detectives, and a variety of west side drug runners.
For the head of a drug syndicate, Prop Joe is also remarkably non-violent, preferring peaceful resolutions to most disagreements. Joe finds these types of solutions to be most lucrative and his keen business sense constantly has at least one eye on the profits.
He is frequently seen fiddling with broken radios, timepieces, and a variety of other devices.
Joe is quite a big man, but his portly size almost lends to his amicability. He is admired by many players in the drug game and is definitely the least divisive and least hated of any of the drug heads (i.e. Marlo Stanfield, Avon, Stringer Bell) in the series.
Played By: Robert F. Chew
What Seasons: In The Wire complete series, seasons 1 - 5 (actually, Joe is 1 of only 3 players in the drug game to appear in all five seasons of The Wire... the other 2 being Poot and Wee-Bey Brice).
My Favorite Scene: The Proposition Joe flashback scene that shows his days as a kid in school selling answers to an upcoming test. He seems to have had that business sense far before he entered the drug game.
Favorite Quote: "Wanna know what kills more police than bullets and liquor? Boredom... You keep it boring, String. You keep it dead bleeping boring." With Avon in prison, Stringer Bell initiates an arrangement with Proposition Joe to secure heroine supply in return for corners on Baltimore's west side. This line from Prop Joe is a fantastic demonstration of his drive to lessen physical violence in the hopes of maximizing profits.
Best Foil / Rival: The West Side Kingpin, Avon Barksdale. Barksdale craves power, Joe wants profits, and Stringer wants both. The Avon Barksdale versus Joe rivalry is considerably more subtle than other rivalries / battles in The Wire, but it exists both structurally (Barksdale operates Baltimore's west side; Joe the east side) and in personality - (Avon does not exhibit the business savvy of a Proposition Joe and his gut instinct is very often violence... as opposed to Joe who doesn't act on impulse but instead takes the most logical path to maximize profits).
Critical Analysis: (see above)