The failure of the levee and floodwall section on the east bank of the 17th Street drainage canal was one of the most catastrophic breaches that occurred during Hurricane Katrina. It produced a breach that rapidly scoured a flow pathway below sea level, so that after the storm surge had largely subsided, floodwaters still continued to stream in through this breach for the next two and a half days. This particular failure contributed massively to the overall flooding of the Metropolitan Orleans East Bank protected basin. Slightly more than half of the loss of life, and a similar fraction of the overall damages, occurred in this heavily populated basin. There are a number of important geotechnical and geoforensic lessons associated with this failure. Accordingly, this paper is dedicated solely to investigating this single failure. Geological and geotechnical details, such as a thin layer of sensitive clay that was laid down by a previous hurricane, proper strength characterization of soils at and beyond the toe of the levee, and recognition of a water-filled gap on the inboard side of the sheet pile cutoff wall are judged to be among the most critical factors in understanding this failure. The lessons learned from this study are of importance for similar flood protection systems throughout other regions of the United States and the world.