The original Wingman was introduced in 1951 in the pages of Batman #65, "A Partner For Batman." In that story, Batman (Bruce Wayne) recruits Wingman to be a costumed crime-fighter—a version of Batman for Europe. In this version, his costume was bright red and yellow, much like Dick Grayson's Robin costume minus the green. He would also appear in the pages of Batmen of All Nations.
The character was then abandoned for many years until writer Grant Morrison resurrected him for use in his run on the Batman books (2007). Morrison's version of Wingman looks similar to Bruce Wayne's blue and gray Batman costume (1970s). In a three issue arc (Batman #667-669) where a man named John Mayhew calls together the Club of Heroes once again, Wingman is quarrelsome. He denies that he has ever worked with Batman and claims that he came up with the idea of crime-fighting first. In fact, Wingman and John Mayhew are accomplices who have called the Club members together to murder them. Wingman kills the Dark Ranger, and attempts to kill the others. However, John Mayhew dissolves the partnership and kills Wingman.
Following the events of Flashpoint, the new Wingman is the leader of a group of lesser known heroes calling themselves, unofficially, The Dead Heroes Club, an off shoot of Batman Inc. The other members are The Hood, Freight Train, Looker, Batwing, El Gaucho, and Halo. The new Wingman is also slated to partner up with Damian Wayne who is operating under the pseudonym "Red Bird" as a bounty has been placed on Robin. It eventually turned out that this new Wingman was Jason Todd, with Batman giving him the mantle as a means of redeeming his reputation.