Engineering is about making and doing things that have not been done before. To be successful, it is essential that engineers properly anticipate how things can fail, and design accordingly. Case studies of past failures thus provide invaluable information for the design of future successes. Conversely, designs based on the extrapolation of successful experience alone can lead to failure. This paradox will be explored in the context of historical case studies, including the design of ocean liners and also of suspension bridges, which from the 1850s through the 1930s evolved from John Roebling’s enormous successes—culminating in the Brooklyn Bridge—to structures that oscillated in the wind and, in the case of the Tacoma Narrows Bridge, twisted itself apart and collapsed in 1940. Lessons learned from these cases and others can be generalized to apply across a broad spectrum of engineering structures and systems.