Ending his first term, Jesse is a successful businessman (he owns a state-wide chain of car dealerships and rental agencies), and Winchester wants to be re-elected. His first term’s theme was “A new broom” and he’s hoping to make law and order a significant part of the second term.
As part of that, he really wants the Steel City Sentries reactivated. He’s made sure that the connections to the Steward Reed building are good, and that the building can be reactivated if need be. He’s even had the police go through and clear out some squatters on the lower floors, and has made a deal with Pieter Schell that some of Schell’s corporations will lease the bottom floors. Floors five through twenty-one are still unoccupied.
Think of Herman Cain. He’s personable and he’s got the kind of straight-shooting simple answers that appeal to the people. In practice, he’s not afraid to cut deals in order that it all look simple.
Winchester has a wife, Dolores, and two grown children: one in her last year of university at Harvard (she’s studying corporate law), and his son has graduated and gone to work in the Peace Corps.