Nearly two feet long with striking black, white, and red plumage, the Ivory-billed and Imperial Woodpeckers were two of the most impressive woodpeckers in the world. Both species were known to be in serious decline by the end of the nineteenth century and are likely extinct today, though occasional reports of sightings persist. While the Ivory-billed was one of the first endangered birds to receive intensive conservation attention, the efforts were too often misdirected, and too little, too late. Concern for the fate of the Imperial Woodpecker came even later and resulted in a similar fate. The probable extinction of two of North America’s largest and most charismatic birds has much to teach us regarding conservation efforts, especially as many other species face similar problems. In closely examining the history of the decline and causes of extinction of the Ivory-billed and Imperial Woodpeckers, the authors offer explanations for the birds’ demise and strategies for future conservation and research efforts that focus mainly on the deadly, though largely understated, role of human depredations.