His "success" comes across as "old cincinnati" to me, the one where there's no clear reason and as you said, very appearance-based. Almost like it's rigged. His backstory reads a bit like that of johnny appleseed's or john henry's.

As for the high schoolers, maybe I've been reading about another Jeff too much lately (Epstein), but, have a look at this exchange from the "Fort Thomas Matters" post. It reads like a plant/something someone was put up to so the reporter could share it during the interview:

Jeff: (speaking like a high schooler) "Y u follow me anyway."

High school athlete: "what"

Jeff: "just wondering what makes u kids follow the ol man didn't mean it the way it came off son"

high school athlete: "everyone wants in the Ruby tribe. it's more exclusive than Augusta national."

I mean... what on earth? the "Ruby tribe"? What does that do for a highlands football player that his parents/others don't already?