Q From Skip Huffman: Can you give a bit of history on the little orphan phrase to boot? It looks like it should be related to the historic pirate’s booty, or even bootlegger.
A Don’t be confused by apparent associations with boot for the heavyweight footwear, from which we also get boot in the sense of restarting a computer. The only one of your three terms linked in this way is bootlegger. Booty comes from Middle Low German buite, exchange or distribution.
To boot usually means “in addition, besides, moreover”, as here in Falk, by Joseph Conrad: “At all events he was a Scandinavian of some sort, and a bloated monopolist to boot”. The phrase can sometimes contain the idea of some positive outcome or advantage, not just something additional. In this, it’s reflecting its ancient origin in Old English bot, advantage, remedy. It’s of Germanic origin and is related to Dutch boete and German Busse (a penance or fine) as well as to the English words better and best.
Boot could at one time exist alone with the idea of profit or advantage (along with its opposite, bootless). Shakespeare uses it this way in Antony and Cleopatra: “Give him no breath, but now / Make boot of his distraction” — in other words, take advantage of his being distracted. It also turns up in several terms from feudal times that referred to the right of tenants to take materials from the manor for their own use, such as firebote, hedgebote, and housebote, in which it can be translated as “benefit”.