Bob Bridwell was born in Edgar, Nebraska in 1932. Following time in the service, he enrolled in an engineering program at Heald Collge in San Francisco, eventually joining San Francisco Bay Toll Crossings as a Junior Engineer. In this interview, he shares his perspectives on transportation in the Bay Area, the evolution of the San Francisco Bay Area environment, and the various influences and problems facing bridge engineers in this era. This interview also discusses the impact of evolving environmental regulations on the maintenance of toll bridges in the area and offers perspectives on the dangers of working on bridges high above spans of water. Bridwell offers memories on the response to the October 17, 1989 Loma Prieta Earthquake and the significance of environmental factors for bridge engineering. Bridges discussed in this interview include the San Francisco–Oakland Bay Bridge, Richmond-San Rafael Bridge, San Mateo-Hayward Bridge, Golden Gate Bridge, Benicia-Martinez Bridge, Carquinez Bridge, and the San Diego-Coronado Bridge.