According to legend, a unique popcorn, peanuts and molasses confection, that was the forerunner to Cracker Jack caramel coated popcorn and peanuts, was introduced by F.W. Rueckheim and Brother, at the World's Columbian Exposition, Chicago's first World's Fair. In 1896, Louis Rueckheim, F.W.'s brother and partner, discovered the process for keeping the molasses-covered popcorn morsels from sticking together. Louis gave the treat to a salesman who exclaimed, "That's crackerjack!"
"Crackerjack" was originally a noun, appearing in the U.S. around 1895, meaning "a person of excellence, superior knowledge and ability." The root of "crackerjack" is a sense of "cracker" current in the early 1860s meaning "a remarkable individual" or "an outstanding example of something." This sense of "cracker" was based, in turn, on a very old (around 1460, in fact) sense of "to crack" meaning "to boast or brag." The "jack" element of "crackerjack" doesn't really mean anything. Its role in the word is to rhyme with "crack." (You know how much I adore rhymes and ditties.)
Speaking of ditties, the song "Take Me Out to the Ball Game" written by Jack Norworth and Albert Von Tilzer in 1908, immortalized the snack with the third line, "Buy me some peanuts and Cracker Jack." Since 1918, Sailor Jack and his dog, Bingo, have appeared on the packages. I noticed Jack and Bingo have a new updated 21st century look. In 1964, our Columbus, Ohio based Borden, Inc. purchased the Cracker Jack Company, and in 1997 Borden sold it's division to Frito Lay. The new packaging is okay, but come on; the prize needs a little work.
last two photos borrowed from Google images