Sudhir Venkatesh
Sudhir is both writer and protagonist; A good student of Sri Lankan heritage, he is currently undertaking his doctorate at the prestigious University of Chicago, studying under eminent sociologist Bill Wilson. Whilst he respects Wilson he has a very strong idea of what he wants his doctorate to be, and this differs greatly from what Wilson believes it should be. Sudhir is a strong-minded and principled individual who shows great determination and courage in going into the poorest of Chicago's projects and reaching out to the leader of the most violent gang.
There is something in Sudhir that likes the danger of his task. He enjoys the process of getting to know the gang's leader and surprises himself by realizing that as men, they are really not that different. They get along easily and have many interests in common. Both are college graduates. Both are consistently near the top of their class in all areas of their lives. Sudhir is confident that he can take on the role of gang leader for a day because it does not seem to be that difficult. He shadows J.T. and becomes even more convinced that he can do it. It is much harder than he imagines.
Sudhir creates a genuine friendship with J.T. and they remain in touch. Sudhir has several epiphanies in the years after his study of the gang. He realizes that in many ways he used the gang members in exactly the same way that J.T. did - by using them to achieve a goal of his own and to further his own career. True, he did it without a gun, but his intentions were the same. He is able to view himself honestly and this quality speaks very highly of his character.
J.T.
J.T. is the leader of the Black Kings gang. He is an intelligent man with a college degree, and he used to have a successful and promising position in sales. He was, in short, Corporate Joe. However, as a pragmatic man he realizes that he can make more money as a gang leader - much more money. In order to make this role more palatable to himself he sees himself as part vocational guru and part Robin Hood, ploughing his ill-gotten gains back into his community which he loves very much. He is a family man and particularly adores his mother.
J.T. is primarily a drug dealer but has several side-hustles going on at the same time, including prostitution and petty theft. He is a good manager with personnel skills that would probably work very well in the corporate world that he rejects.
Whilst most of the characters in the book see a marked improvement in their lives as the projects are demolished and better housing built in their place, J.T. sees a downturn in his fortunes. As there are no projects there is no drug trade, and without his position as a dealer he is not as useful to the Black Kings anymore and is ultimately sidelined.
C-Note
C-Note is not a drug dealer but he is affiliated with the Black Kings. He runs a car cleaning and detailing business, accepting the cars of gang members with no questions asks, and removing any incriminating marks or details from them. He has a good relationship with J.T.
T-Bone
T-Bone is J.T.'s Second Lieutenant and is responsible for micro-managing the foot soldiers that are sent out to do the physical selling and delivery of J.T.'s drugs. He is loyal and also a hustler, creating money making opportunities seemingly out of thin air.
Ms Bailey
Ms Bailey is a crooked elected official. She is seen as very powerful and strong, and she covers up her brutal and unfair side by showing Venaktesh how much she cares about her community. It is not that she steals from the residents of the Robert Taylor Homes; they get the money they are entitled to. However, she gets a substantial kickback from every foodservice and supplier, construction service and supplier, and any other business involved in any improvements. She does improve conditions, but the person for whom conditions improve the most as a result of her involvement is definitely herself.
