Hefner brings to mind the lost souls in C.S. Lewis' The Great Divorce who are inexorably drifting off into deep space, utterly and forever alone.
In reality, he doesn't even OWN his mansion anymore. He rents it from Playboy enterprises.
And this was a guy who at one time did own a private jet.
Wouldn't surprise me if he's nearly broke.
The mansion may look great from the outside, but apparently is a total pigsty inside. And the author of that book reveals that not one of those girls would be with Hef unless he was paying for their cosmetic surgery and giving them a weekly allowance.
Oh, they think he's "nice", but still just a decrepit old man.