Quite apart from any question of their validity, the imposition of use restrictions by means of a prohibition was not practicable before the development of equitable remedies because the common law afforded no method of enforcing such a prohibition. One who conveyed land in violation of a prohibition on alienation might attempt to enforce the prohibition by attacking the validity of his own conveyance but one who violated a prohibition on use had neither motive nor method for challenging his own acts. Hence attempts to restrict use by common law devices are necessarily confined to penalty restraints and to limitations on the interest, as distinct from the activities, of the user. The real covenant, as enforced at common law, is a penalty restraint; the easement is a limitation on the interest of the user. Defeasance by condition subsequent is a penalty restraint; defeasance by special limitation is ordinarily a limitation on the interest of the user; defeasance by executory limitation may be both.
William F. Fratcher,
Defeasance as a Restrictive Device in Michigan,
Mich. L. Rev.
Available at: https://repository.law.umich.edu/mlr/vol52/iss4/3