Caught again by the paparazzi

My brother sends me photos of Max. He catches him doing things that I don't see. For example, the above pic must have been taken when Max was in LA with his peeps. This photo is reminiscent of Turtle from Entourage, don't ya think?

In the one below, I'm not sure what Max's Uncle Brett is implying. Hmmm. He placed him between Winston Churchill and WC Fields. Is he saying that Max looks like a fat old man in a funny hat? Or is he saying that Max is on the right track to being a politician or entertainer? Or is he saying Max is a member of an ancient organization known for flashing strange gang signs for photo ops?
I'll ask Max about it when he wakes up.