They should ask. There are a few endowed scholarships from former players: Ditka, Wanny, Foge, Corky Cost, Pete Varischetti,Walter Bielich, Ernest Westwood, Marshall Goldberg, Steve Petro, Herb McCracken, and maybe a couple others. You have others like Fralic, Covert, Pelusi, Pat Bostick, Jeff Christy, and Doug Whaley that give significant amounts regularly. That's not a complete list, but there are a lot of missing names that may not fall under "anonymous." Often all it takes is someone to ask.
I would consider creating an endowed football alumni scholarship fund as part of the Varsity Letter Club with contributors listed separately and see if soliciting can that can spread around the football alumni. Heck, I'd do that for every sport and put it in each year's media guide for every individual sport with a graph of progress for what is need to fully endow that sport which I'd then mail to every alumni of that sport with the request for contributions.