Suppose that prior to the year 1285, ye olde Harvey Grutz, the owner of Blackacre in Fee Simple Absolute, conveyed Blackacre "to Arnold Schwarzenegger and the heirs of his body." The courts in merry olde England construed this as creating a Fee Simple Conditional in Arnold and because Grutz thus conveyed away less than all of his Fee Simple Absolute, Grutz retained a Possibility of Reverter.
What is a Fee Simple Conditional? Notice that it is completely different from the Fee Simple Subject to a Condition Subsequent. I repeat: a Fee Simple Conditional is not a Fee Simple Subject to a Condition Subsequent. Do not confuse these two very different estates merely because their names are somewhat similar.
Moynihan describes a Fee Simple Conditional "as if it were to A and his heirs on the condition that A have an heir of his body." In other words, in our example above, prior to 1285 the English courts "held that, upon the birth of issue to [Arnold], the condition had been fulfilled and [Arnold then] had the power to alienate the land in fee simple. But, the courts did not go so far as to hold that [Arnold] acquired a fee simple for himself. Thus, if [Arnold] had issue but later died without any issue who survived him and [Arnold] had not alienated the land to another during his life, the land reverted to the grantor even though [Arnold] had surviving collateral relatives."
As Prof. Moynihan points out, this construction by the courts of a conveyance "to Arnold and the heirs of his body" was "undoubtedly influenced by the judicial bias in favor of free alienability of land, but it ran counter to the intention of many donors."
Suppose, for example, that the donor's nephew was about to marry and the donor wished to give his nephew, as a wedding present, land that would remain in the nephew's family from generation to generation. The donor did not wish the land to be sold outside the family in fee simple, but to remain in his nephew's line of descent from generation to generation, and upon failure of the nephew's line of descent it was the donor's intention that the land would revert to the donor.
Again as Prof. Moynihan observes, construction of the gift as a Fee Simple Conditional (rather than as a Fee Tail), allowed the donee "to defeat the rights of both his issue and the donor." Do you see how?
To return to our earlier hypo (Grutz "to Arnold and the heirs of his body"), Arnold has a Fee Simple Conditional and Grutz has a Possibility of Reverter.
Suppose one year after the conveyance, Arnold's wife gives birth to their son, little Conan? The next day, Arnold conveys "to Lou Ferrigno and his heirs." Now what is the state of the title?
Answer: Ferrigno has a Fee Simple Absolute (Arnold had the power to convey a FSA and he exercised that power).
Now suppose Arnold does not convey away the land, but dies survived by his son Conan. What is the state of the title?
Answer (from a popular Hornbook): "If the owner [i.e. Arnold] dies survived by issue before making an inter vivos transfer, the issue will take the fee simple conditional by descent. This means that the condition as to birth of issue must again be satisfied before the estate can be converted into a fee simple absolute by inter vivos transfer."
Now suppose Arnold dies without issue still owning the Fee Simple Conditional?
Answer: Now the land will revert to the grantor, Grutz, as a result of the failure of issue under Arnold's Fee Simple Conditional.
