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What is the origin of the word “bootleg”?

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You could find that answer from any number of online etymology dictionaries, including etymonline.com or dictionary.reference.com (not restricted to etymology). – F'x Feb 20 '11 at 12:45

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The New Oxford American Dictionary has:

ORIGIN late 19th cent.: from the smugglers' practice of concealing bottles in their boots.

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It's roughly the same for football, where a "bootleg" means the quarterback fakes a handoff and runs out of the pocket while concealing the ball (ostensibly on his leg). – mmyers Apr 7 '11 at 15:52
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Originally bootleg liquor, it came from smuggling a flask hidden between your boot and your leg

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Online sources seem to agree with you, but I don't buy it. Regardless of the shape of the bottle, any boot-leg loose enough to let you secret a bottle there without hobbling yourself would also allow the bottle to bounce right out. I would sooner believe that the bootlegger is concealing paperwork (tax stamps, blank prescription forms) in his boot. – Malvolio Jun 24 '11 at 21:48
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To give you a little when and where that can't be found with a point and click, I searched for earliest print references of the smuggling sense of bootleg. Most mention Kansas, the first state to pass prohibition laws in 1880, but there is also this early reference from Iowa in the Pharmaceutical Record, Volume 9, 1889:

The permit system, without giving any protection to the druggist, is a continual source of annoyance and makes a cover for the bootlegger who sells the whisky, takes the money and lets the druggist shoulder the responsibility of censure for the drunkenness prevalent in the town where he lives.

The first Kansas reference is from the Biennial Report of the Attorney-General of Kansas, Volume 1, 1889:

MCPHERSON COUNTY.—The prohibitory law in our county is as well enforced as could reasonably be expected; in fact, there have been no open violations of the law for many years, that I can remember. The "bootlegger" now and then infests our county, but he is ordinarily short-lived [...]

And we get our first definition of the term from B. R. Porter, Probate Judge of Anderson County, Kansas, in The Economics of Prohibition, 1890, requoted from an 1889 report in The Voice:

http://books.google.com/books?pg=PA198&id=gk4ZAAAAYAAJ#v=onepage&q=bootlegging&f=false

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