As I will examine in this study of waterfront redevelopment at Jack London Square, the business plans, architectural/landscaping designs, and historic memorabilia drummed up by Oakland civic, business and port leaders, from 1951 through to the early twenty-first century, repeatedly changed their focus as a result of cross-bay rivalry. The two cities had long competed for businesses and residents, using city planning to improve their transportation infrastructure and, later, their tourist draw. From 1951 through the 1960s, themed restaurants in Jack London Square multiplied, and the Port of Oakland cobbled together seafaring artifacts and Jack London memorabilia. Starting in the 1970s, private businessmen and the Port took on grander retailing approaches that progressed from a woodsy maritime village to a shopping mall to an artisanal foods market. Each time, Jack London Square was made over in light of events across the bay: the 1960s conversion of brick warehouses and factories into the retailing/restaurant venues of Ghirardelli Square and the Cannery; the late 1970s construction of a vast shopping and entertainment complex on Pier 39; and the early 2000s redevelopment of the Ferry Building, closer to downtown San Francisco, into a locavore food emporium. Yet each time, Oakland’s attempts to compete with San Francisco fell short.