Entail is the tradition of transferring productiveassets, typically income-producing property, inperpetuity. Although the practice of entail hasunderscored much of our history and literature, it islittle understood and rarely studied. Arising fromstudy of economic regeneration and revitalization bythe author from his experience as a venture capitalpartner, this work traces the history of entail fromancient times. Its purpose, owing to lawlessness andinterfamilial rivalries in ancient and medievaltimes, was to retain control of the bulk of suchassets in the hands of strong male descendants whocould "protect the keep". As governments wereestablished, entails served to support aristocraciesand monarchies and provided scaffolding for civilsocieties. Settling of the New World was stimulatedin part by a desire to escape from the limitations ofentail in Europe and England, as the majority of theproductive land was tied up in perpetuity incontracts that could not be broken. When consideringthe need for economic regeneration, coupled withdesires to ensure the well-being of family members,we would be well-served to consider this aspect ofour history and tradition.