I grabbed a few uses of the word entail from Twitter. Someone was tweeting about what new health care laws might entail; another person asked a friend about what a change to their plans might entail.

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The sense here is that entail means “require.”

That is consistent with the meaning of entail since its emergence in English more than 600 years ago but the rest of the word’s history isn’t exactly what you might expect.

The word entail does literally mean “to attach a tail to” and we could guess that this might be a metaphorical sense of imposing a restriction, but there’s more to it than that. In this case the word tail does not refer to a long appendage that one drags behind. This tail comes from the French word taillie that meant “to cut.”

Before anyone was talking about what a change in their plans for the weekend might entail the word entail had a strict and narrow legal meaning. It had to do with imposing limitations on the vast tracts of real estate owned by the rich and influential in England.

The source of most wealth of aristocratic families was the land they owned. They made their money by having the common people work the land and pay rent on it, either in cash or goods or labor.

Since there was no such thing as birth control a rich family, like a poor one, would likely have lots of kids. If you start forking out sections of the back 40 to half a dozen kids every generation, before long your cash flow no longer qualifies you as noble and aristocratic.

Hence the family land had legal encumbrances placed upon it so that only the oldest male descendant could take possession.

That’s what entailment meant at first.

The “cut” meaning of tail has been explained in some places as being a cut to the rights or abilities of the owner in how the pass the property along, but most dictionaries point instead to a sense of “cut” meaning that the legal obligation is cut or shaped into a precise and unchangeable form as if it were set in stone.