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This essence of this proverb dates back to at least the late 14th century in English and to the early 13th century in German.
The earliest extant reference is in the work of Freidank, an early 13th century didactic poet (i.e writer of poems intended to teach) who is thought to have lived somewhere around Swabia, which was part of the German kingdom of the time. His version translates something like:
The wise tell us that a nail keeps a shoe, a shoe keeps a horse, a horse keeps a knight, a knight, who can fight, keeps a castle.
The earliest surviving reference in English is by John Gower in the late 14th century in his expansive poem Confessio Amantis ("The Lover's Confession"). Gower was a contemporary and friend of Geoffrey Chaucer so its safe to say that his Middle English version of the expression would be almost as unintelligible to most modern English speakers as Freidank's Germanic version is.
Where things get confusing is where the proverb in its modern form - including the reference to a lost kingdom - originated. Many sources point to it being a reference to Richard III of England's defeat at the Battle of Bosworth Field in 1485. But there is a bit of a hole in this from an historic perspective as it would seem that Richard's horse did not lose a shoe but got stuck in the mud.
Maybe we have Shakespeare to thank for the introduction of the concept of the loss of the kingdom due to the loss of the horse:
A horse! a horse! my kingdom for a horse! (Richard III, Act V, Scene IV)
But versions of the expression between Shakespeare's time and up to the 20th century don't appear to reference "kingdom". For example, in 1758 Benjamin Franklin in The Way to Wealth wrote:
For want of a nail the shoe was lost,
for want of a shoe the horse was lost;
and for want of a horse the rider was lost;
being overtaken and slain by the enemy,
all for want of care about a horse-shoe nail.
Some think that the lack of "kingdom" in American versions was due to the irrelevance of kingdoms to the newly formed United States of America, but there appear to be a lack of "kingdom" references in British versions as well.
Where the whole thing seems to come together is in "The Horseshoe Nails" by James Baldwin (1924-1987), one of the stories in his Fifty Famous People. The story ends:
"For the want of a nail the shoe was lost;
For the want of a shoe the horse was lost;
For the want of a horse the battle was lost;
For the failure of battle the kingdom was lost;—
And all for the want of a horseshoe nail."
It seems difficult to believe that James Baldwin was the first to include the use of "kingdom," but with no evidence to the contrary, this is where our trail ends!
Updates:
Becky writes: "I remember this phrase being used in a book I read as a child (unless my memory has betrayed me) - What Katy Did by Susan Coolidge, published in 1892.
Lexicop writes: "I heard this poem many decades ago, and my memory is clear on the terms being not "horseshoe nail" but "two-penny nail" The latter better highlights the disparity between the high cost of the lost kingdom and the trivial expense of the nail: It makes better poetic sense. But I cannot document this reading. Any thoughts?"
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