Posted by R. Berg on April 16, 2001
In Reply to: Bootleg posted by Bruce Kahl on April 16, 2001
: Any info?
You betcha. Dict. of Amer. Slang gives only meanings for it, not origins--but see below. As a noun: Coffee, esp. inferior coffee. (Since c. 1915. A little Armed Forces and prison use.) Bootleg liquor [hmm--sounds circular to me]. (Since c. 1920. Not common.) As a verb: To carry the ball deceptively, as in football and other sports.
Amer. Heritage Dict. says "From smugglers' practice of carrying liquor in the legs of tall boots." There is also a literal definition, "The part of a tall boot above the instep."
The Supplement to the Oxford English Dict. says much the same thing, but at greater length.