On a much smaller scale, it reminds me of Steeler running back, "Frenchy Fuqua", in the mid 70s.
He was a good back, never a super star and never made large money, but spent like he really had some.
I'd be in some of the downtown clubs when Frenchy and his entourage, consisting of a couple of brothers and 3 or 4 hookers would come into the place.
Regardless of how many were in the place {when he came in the night, usually several hundred} he would set up drinks for every one.
When his career was over he was delivering newspapers in Detroit, after he had declared bankruptcy.
Living large with the Detroit Free Press.
I remember Frenchy. If I remember correctly, he had a pair of platform shoes with a goldfish in the platform.