General History
Traditionally, a fee tail was created by words of grant in a deed: "to A and the heirs of his body". The crucial difference between the words of conveyance and the words that created a fee simple ("to A and his heirs") is that the heirs "in tail" must be the children begotten by the landowner. It was also possible to have "fee tail male", which only sons could inherit, and "fee tail female", which only daughters could inherit; and "fee tail special", which had a further condition of inheritance, usually restricting succession to certain "heirs of the body" and excluding others. Land subject to these conditions was said to be entailed or in tail, with the restrictions themselves known as entailments.
Fee tail was formerly used during feudal times by landed nobility in order to create family settlements and to make certain that the land stayed "in the family". From the foregoing, attempting to mortgage land in fee tail would be risky and uncertain, since at the death of the owner the land passed by operation of law to children who had no obligation to the mortgage lender and whose interest was prior in right over the mortgage. Similarly, the largest estate an owner in fee tail could convey to someone else was a life estate, since the grantee's interest again terminated automatically when the grantor (the original owner) died. If all went as planned, it was impossible for the family to lose the land, which was the idea.
Things did not always go as planned, however. Owners of land in tail occasionally had "failure of issue"—that is, they had no children surviving them at the time of their own deaths. In this situation, theoretically the entailed land went back up and through the family tree to descendants of former owners who were entitled to inherit, or to the last owner in fee simple. This situation produced complicated litigation.
Fee tail was a device tuned to the needs of family settlements in the thirteenth century, but it was never popular with the monarchy, the merchants, or many entailed holders themselves who wished to sell their land. In more mercantile eras, fee tail became rare. As early as the fifteenth century, lawyers devised an elaborate action called "Common Recovery", which used collaborative lawsuits and legal fictions to "bar" an entail, i.e., remove the conditions of fee tail from land and enable its free conveyance in fee simple. In the 17th and 18th centuries the practice arose whereby a landed estate would be settled on a man for life, and thereafter to his eldest son in tail male; when the son came of age, he and his father together could bar the entail, and would then re-settle the land on the father for life, then to the son for life, and then to his eldest son in tail male, at the same time making provision for the father's widow, daughters and younger sons. In this way an estate could stay in a family for many generations. It also had the advantage that if an heir appeared irresponsibly spendthrift to his father, the entail could be retained to protect the estate.
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