Rich guys generally don’t go cruising down sunset blvd in their Maseratis.
Generally these women are at country clubs, parties, etc where wealthy men attend. Men know what the women want and the women know what the men want.
She gets her rent paid, new car, expensive gifts and she is his arm candy, dinner companion, bed room playmate. She would be considered his “girlfriend” but really isn’t.
Cops never run stings on these type of arrangements, even though they are technically “prostitution” by the legal definition. Mr. Kraft could have easily set something like this up, and nobody would care. And a few 100K for rent/cars/gifts to a billionaire is nothing.
But cops don’t go after wealthy guys, just average Joes with 100 bucks in their pockets at “massage parlors”.
Mr. Kraft is an idiot, I have no idea why a man of his stature would even want to be seen at one of those low brow massage parlors. Likely no one would recognize him, but still.
But it's "too safe", I think part of the thrill of doing it, is the specter of getting caught.