|First appearance||"Boys of Summer" (episode 4.01)|
|Occupation|| Mayoral Senior Aide
|Portrayed by||Reg E. Cathey|
Wilson is a professional political operative who serves as councilman Tommy Carcetti's deputy campaign manager in his run for mayor of Baltimore, under campaign manager Theresa D'Agostino. Wilson is practical minded and organized, essential qualities because he is tasked with keeping Carcetti on a strict schedule. Wilson was once a night editor for the Baltimore Sun and has many connections amongst the city's media. He is an honest voice in Carcetti's campaign and is often the sounding board for Carcetti's worries about race in Baltimore politics. When poll results do not go in Carcetti's favor he loses interest in the campaign believing that it is impossible to win. Wilson is left to keep his candidate on track despite his pessimism.
After Carcetti wins the primary and subsequent election, D'Agostino moves on, but Wilson continues to serve as his right hand man, accompanying the newly elected mayor everywhere he goes. At the end of the season, Wilson gets disillusioned with Carcetti, who puts his own ambition above the needs of the city. He talks with Clarence Royce's former advisor, Coleman Parker, and muses about managing the campaign of another up and coming politician on the Eastern Shore of Maryland.
Despite his misgivings Wilson remains on Carcetti's staff for the next year and watches the Mayor struggle with the budget crisis while still planning his run for Governor. Carcetti is aware of Wilson's feelings about his decision but still seeks his counsel.
|Season four appearances|
|Boys of Summer||Soft Eyes||Home Rooms||Refugees||Alliances|
|Margin of Error||Unto Others||Corner Boys||Know Your Place||Misgivings|
|A New Day||That's Got His Own||Final Grades|
|Season five appearances|
|More with Less||Unconfirmed Reports||Not for Attribution||Transitions||React Quotes|
|The Dickensian Aspect||Took||Clarifications||Late Editions||–30–|