While it’s true that to boot a computer means to start its operating system, when someone adds “to boot” at the end of a comment, they mean they got something pleasantly unexpected added to the deal.
On October 27, 1900 the New York Times carried an interesting story entitled, “Says Husted Traded Wives.” The story was told by a Mrs. Lizzie Sherow with whom Oliver Husted eloped to Holly, Michigan. The story began with this:
Oliver Husted of Schultzville, this county, accompanied by Mrs. Lizzie Sherow, for whom he had traded his wife and given $10 to boot, were brought into the police station here to-night by Chief of Police McCabe, who had just arrived with his prisoners from Holly, Mich., where they had been arrested on the charges of grand larceny and kidnapping.
In the George Nichols autobiography entitled, “Salem Shipmaster And Merchant” the following is written:
It was in July, 1802, at Manila, where I employed a Mr. Kerr, to assist me in my business. He took a great fancy to my watch and proposed giving me his watch with some indigo to boot in exchange for it, and we finally fixed upon a quintal and a half, worth then more than $160, and I retained my chain and seals. This indigo I afterwards sold for $130 more than the original cost of my watch, besides getting a watch, which proved a better timepiece than mind had been.
In 1710, Chesterfield-born Gilbert Heathcote (1652 – 1733) — son of ironmonger Gilbert Heathcote and his wife, Anne — was serving his first term as Governor of the Bank of England which was established in 1694, he ran for office of Lord Mayor of London. Documents of the day state that he is not only “a Whig but a prosperous merchant to boot.”
The expression is found in one of the Creole dialect mixtures used in Southern Louisiana and Mississippi ands literally translates into “the gift to give more.” In other words, it denotes a bonus that a friendly shopkeeper adds to a purchase as an unexpected gift of benefit.
It’s also found in Middle English where the word boten means “to be of help” which comes from the Old English word btian meaning “help.” What’s more, the Old English word bōt and the Middle English word bote mean “an advantage or something included in a bargain.” And then it’s also found in Proto Germanic word boto that means “better” and the word Buße that means “penance” or “atonement.”
The cross-over between languages happens because there are corresponding words in English, French, Provençal, German and Spanish that are similar in nature and have a similar meaning to each other.
There are records of the expression to boot being used in commerce as early on as 1000 A.D. and continues to be used in today’s conversations.