First there are several Indian casinos in Michigan and Minnesota that were open with live gaming long before "compacts" were ever heard of.
Thanks to Bob Matthews and a friend of his that traveled that area on business and was willing to stop and pick up chips for us, we have some early chips that not to many others have.

Fond-Du-Luth Gaming Casino, in an old hotel right in the center of downtown Diluth, Minn. opened sept.0f 1986 by making their own private deal with the city.The earliest chips I have from this one are horses heads right. Live gaming was shut down in 1991, slots remained, and then re-opened in 1995 when "compacts" were finally settled with the state. My earliest slot token is 1991, that indicates to me thts when I got the hrs hds rt chips, just before live gaming was closed down. Which also indicates there could have been an earlier set of chips.
To add to this story, that may be a large clue to Don's $50 chip--- Saginaw Chips Cardroom opened at Mt. Pleasant, Michigan Febuary 1987 WITH a set of small key chips. The first set didn't even have a name, just amount on one side & Indian Design on the other side. In just a few short months another set of small key chips were added, this time with name on the amount side. The clue seems to be that the numerals on Don's $50 chip from Diluth and my 50-cent chips from Saginaw seem to be exactly the same.
From this my guess is the original set of Fond-Du-Luth chips could very well have been the same key mold. This fits the time frame.
From Saginaw Chips I have 50-cent, $1, $2, $5, $10, & $25. My memory does not hold enough to rember if there were $50 chips there and my budjet didn't allow me to even look at higher values.

Janice & Jerry O'Neal