Kenneth Jackson
Kenneth Jackson is a professor of the history of New York City and of military history. His popular New York City history course requires an absurd number of field trips but also features a midnight bike ride from Columbia to Brooklyn, for which participants receive a free t-shirt. After being canceled for a number of years, the bike ride has been recently reinstituted. Nevertheless, the remainder of the class is reportedly boring, and consists of Jackson showing many films in which he is a guest speaker.
Despite writing a polemic against suburban sprawl, Jackson owns a palatial residence in Westchester County in addition to his apartment on the Upper West Side. He also owns a zippy sportscar to get between them. In his spare time, Jackson runs the New York Historical Society.