Why are cigars called “stogies”?
Tobacco was picked up from the natives of the East Indies and introduced to Europe by the Spanish in the sixteenth century. The English word cigar is from the Spanish cigarro, which they took from cigarrales, a Cuban word meaning a place of leisure. Stogie is an abbreviation of Conestoga, and because the drivers of that wagon company (based in tobacco country) always had a roll-your-own cigar stuck in their mouths, observers called them stogies.

Why is a tough, all-terrain vehicle called a “Jeep”?
In 1937, the Army introduced a general purpose four-wheel drive vehicle which, when abbreviated, became G.P. At the same time the very popular Popeye cartoon had introduced Eugene the Jeep as a weird little pet for Olive Oil; it communicated by calling “jeep.” The young men in the service put the little G.P. and the cartoon character together and called the vehicle a Jeep.

Why are both the manager of an athletic team and a large passenger vehicle called a “coach”?
The word coach comes from the Hungarian village of Kocs (pronounced “kotch”), made famous for its large, horse-drawn carriages in the sixteenth century. In Britain, the word became coach, and by the nineteenth century took on the second meaning of a sports trainer or private tutor. The implication is that, through his experience and knowledge, the coach, like a bus or a train car, carries the younger trainees to their destinations.