This is what I am talking about.
He needs to be seen as being associated with tough guy successful athletes or people. Anything. It doesn't matter who they are, he wants the rub of being around people he thinks other people are tough, successful, etc. To him being associated with that is the most important thing. That is how he was able to con people in the early 80's, by pretending to be far more successful than he was, associating himself with important people, being seen in public as doing big things, and pretending he was involved in that crowd. It's why he made up fake names and called news outlets and lied to get himself in the press. It's all about the image he sells. Because who would care about some guy who was born rich and never had to do any real work?