I was eating a Tootsie Roll Pop (helping to support a kid wanting to go to space camp) and saw the indian shooting the star on the wrapper and thought I would find out what was on the internet about that, since I'd heard as a kid about something about collecting them or something. And I wondered, since I seemed to always get ones with the indian, if maybe they were on all wrappers now and that there was no longer any point in collecting them.
Turns out that sometime in the 1930's a rumor got started that the ones with the indians were special or valuable because not every wrapper had one. About one-third of all wrappers do, based on the design. It would suggest that some lack certain other children but I guess they aren't as distinctive or obvious as the indian.
Anyhow, the rumor has never been true and the company used to send out apologetic letters saying that there was no such contest. Then in 1982, they invented a short story about the indian and now that's what they mail to kids. Personally? I think they ought to make the indian less likely to appear on the wrapper (change the design slightly, of course) and then actually have a candy giveaway, like two tootie roll pops for every 25 redeemed or something. (Or is it bad to encourage kids to eat lots of candy?)
But, and I thought this was pretty cool, some grocers (most likely small mom and pop stores) would allow young children to redeem the "indian wrappers" for free candy, subsidizing it out of their own pockets.