The great whales of the North Atlantic live, breed, and are now being injured and killed in the “Urban Sea”—a growing feature of the United States coastline resulting from coastal development. The primary threats to great whales are anthropogenic: vessel strikes and entanglement in commercial fishing gear. Despite their popularity as cultural icons, and federal and state protective regulations on the books, endangered whales increasingly suffer collateral damage from coastal commerce. Ample law and technology exist to eliminate these problems. Rather than advancing the protection of whales, however, government agencies and some non-profit organizations have aggravated the problem through their lack of meaningful action. This essay examines systemic reasons why harmful entanglements in commercial fishing gear continue to occur and are likely to go on unabated into the future. The essay then proposes a paradigm shift for approaching these problems that will protect whales and will also benefit other wildlife in the ocean and its coastal Urban Sea.