Etymology

loggerhead

log·ger·head
L1O1G2G2E1R1H4E1A1D2

Today it means: A stupid person; a blockhead, a dolt. Full definition →

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The story

From logger (“(dialectal) heavy wooden block secured to a horse's leg to prevent it from straying”) + head. Logger was apparently coined because its sound connotes a clumsy, heavy object; compare log (“trunk of a dead tree; bulky piece of wood”).

Etymology from Wiktionary, CC BY-SA 4.0.