- (in Western U.S.) a person responsible for driving a herd of cattle.
Origin of trail boss
An Americanism dating back to 1885–90
Dictionary.com Unabridged Based on the Random House Unabridged Dictionary, © Random House, Inc. 2018
Examples from the Web for trail boss
That's the way this fellow had it; said a trail-boss told him at Ogalalla that spring.
"Was trail-boss three seasons for Hank Rowan and his partner," I returned briefly.