 He acted as a city manager for a total of 30 years for the cities of Kalamazoo, Michigan (1977–1984 ); Santa Ana, California; Richmond, Virginia (1986–1997); Oakland, California (1997–2003); and Washington, D.C.(2003–2006).During Bobb's tenure at Oakland, California, the city was governed under a new and unique hybrid system which combined a strong, elected mayor with a full-time professional city manager.Critics had warned of stalemate if the mayor and city manager were to lock horns, but the system appeared to be working for the first two years as the city's bureaucracies were restructured and new policies were adopted.