The Cigar store wooden Indian seemed to have lost the spear or stogie he once held. He must search for it every night, but his feet are strapped to a dolly which might inhibit his movement. Then again he might get around better by kneeling down and using his hands to roll himself around the shop. I thought that a wooden Indian wasn't exactly a politically correct way to attract customers. But what do I know,
Because of the general illiteracy of the populace, early store owners used descriptive emblems or figures to advertise their shops' wares; for example, barber poles advertise barber shops. American Indians and tobacco had always been associated because American Indians introduced tobacco to Europeans, and the depiction of native people on smoke-shop signs was almost inevitable. As early as the 17th century, European tobacconists used figures of American Indians to advertise their shops.
Because European carvers had never seen a Native American, these early cigar-store "Indians" looked more like black slaves with feathered headdresses and other fanciful, exotic features. These carvings were called "Black Boys" or "Virginians" in the trade. Eventually, the European cigar-store figure began to take on a more "authentic" yet highly stylized native visage, and by the time the smoke-shop figure arrived in the Americas in the late 18th century, it had become thoroughly "Indian." People within the Native American community often view such likenesses as a caricature or as depictions that perpetuate stereotypes, drawing an analogy to the African-American lawn jockey, which I've heard is quite popular in Winter Park as well.