“In all the trade of war, no feat
Is nobler than a brave retreat.”
Samuel Butler Hudibras (1684)
When a man preserved his freedom by running away, he was once said to have “given leg bail.” The word “bail” originally denoted a person who legally took an indicted man from the custody of the sheriff, and this “bail” was allowed to take custody because he bonded himself, by word or security, to ensure that the indicted man would appear in court to face trial. Thus a late seventeenth-century handbook for English sheriffs tells us:
“Bail is so called, because the party bailed is delivered by law into the custody of those that are his bail, and who are to answer [for] the party . . .”
The word bail comes from a Latin word that means carry or bear. Because water is carried in buckets, carrying water out of a leaky boat in a bucket is called bailing. Because an airman leaping from a disabled aircraft resembles water tossed from a leaky boat, his leaping is called “bailing out.” There is a connection between the man who is “bailed out of jail” and the man who “bails out of an aircraft,” but it is an indirect one.
A man who gives “leg bail” is therefore out of the custody of the sheriff and under the custody of his own legs. By the late eighteenth century, the definition of the phrase “leg bail” was enlarged to take in any instance where a man preserved his personal liberty and security by flight. Thus the early American ethnographer James Adair said this of an encounter with a threatening Indians band near Charleston, South Carolina, in 1749:
“I had concluded to use no chivalry, but to give them leg-bail instead of it, by leaving my baggage horses, and making for a deep swamp.”
Putting distance between oneself and a threat of injury or captivity was also described as giving “land security,” and indeed the two phrases were sometimes joined, so that to “head for the hills” was to “give leg bail and land security.”***
This use of the phrase “land security” is a rather clever pun, since the word security literally means to be free of troubles, worries and cares. It comes from the Latin secures and is made of the roots se (without) and cura (care). One who takes care of something is, of course, its “curator.” One who is carefree and untroubled by worries is secure. Thus we say a man gives “security” when he places some personal property at risk of forfeit so another party need have no worry that the man giving security will welsh on his debt or renege on his promise. When that personal property is land, it is called land security.
A man who runs away from his troubles actually obtains security by crossing the land (and perhaps even the sea), and thereby leaving his troubles behind. Let me wrap this up with another apposite couplet from Butler’s Hudibras
“For those that fly may fight again,
Which he can never do that’s slain”
*) Anon., The Complete Sheriff (1696)
**) James Adair, The History of the American Indian (1775)
***) Francis Grose, A Classical Dictionary of the Vulgar Tongue (1788)
The Orthosphere 
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“He who fights, then runs away,
lives to fight another day”
I looked that line up when I wrote this. The idea has been around since Roman times, but the authorship of those exact lines is uncertain.
The Scottish phrase to find bail is “to find sufficient caution and surety” – “Caution” being pronounced “kayshun.”
I wonder how this relates to a ‘bailey’ as either the claimed area for use around a fort (a motte, in fact), often ringed with a set of low walls, or as the same sort of land relationship but as the common yard of a prison (and by synecdoche the prison as a whole, thus “the Old Bailey”).
It seems clear there is some relation, but exactly what relation I cannot say.
There may be a connection through the word bailiff. The bailey was surrounded by a stockade or pailing, bail and pail sound very much alike, and there is a common sense of protection.