The nice thing about the internet is when you see some weird ad in your comic books you can look it up and see what the hell they are talking about. I didn't know anything about an Indian Wrapper Legend, but according to Snopes it seems like people somehow got it into their heads that if you got a tootsie pop with an Indian picture on it you could send it in for a free tootsie pop. In fact according to that Snopes article (from 2011), they still get about 150 letters a week asking for free tootsie pops, and some stores feel compelled to give them away because people are so sure about it.

And so this ad seems to have been an attempt to disabuse people of this idea. They started sending out the "secret of the Indian Wrapper Legend" pamphlets and trying to get people to send some money along with their sticky candy wrappers in exchange for hats and towels or whatever.

Weird. But that is one smug looking kid with all his tootsie roll paraphernalia. He earned it, though. By eating candy.