This has been puzzling me. Not that I care much about this dumbass rich guy or his inability to get laid without paying $140 to someone working out of a trailer park in Ohio but... based on my experience rich guys have a fixer to procure prostitutes, drugs, etc. They don't go to the meeting themselves, they send their guy. If it's a bust some rando named Rick or whatever gets their collar felt, the rich person sends someone else to bail him out and the rich guy doesn't end up in the papers. Like, this is seriously common practice. I've known "the guy" and that's how it works. The only conclusion I can come to here is that Jed York is dumber than any of the players on the team he owns. And maybe more broke.