I like how he didn't even change out of his street urchin clothes to win that pony-riding ribbon. This kid definitely deserves a Horatio Alger-style book about his rise from common bootblack to famous Pony Express rider who helped Wild Bill and Calamity Jane out of a scrape or two.
Nearly all of these urchins were discovered in the photography archives of the Library of Congress (and available without copyright restrictions online). Otherwise, urchin photos will be credited to the appropriate photographer with a link to its source (unless they come from my own collection of photographs from unknown photographers). If there is ever a copyright concern, do not hesitate to contact me.