That pinback is for Roosevelt High in Minneapolis. It's definitely not Al Simmons.
Click on this link to worthpoint where you can see this pin was sold along with a group of other Minneapolis pinbacks. You can blow the pic up and see a better closeup pic than what was posted here on 54.
https://www.worthpoint.com/worthoped...ool-1899804535
Here is another one sold in another group of all Minnesota pinbacks.
https://www.worthpoint.com/worthoped...elt-1902503405
Here is the notable alumni list for this school which doesn't include an Al or a Sam. I personally believe it's probably just the head football coaches who faced off in whatever year this homecoming game took place.
https://en.wikipedia.org/wiki/Roosev...l_(Minneapolis)