True, he could of had a specific need (medical, DUI,etc) hadnt thought of that. Also someone mentioned the driver for Philip. As a Mother I dont think I would be keen on a race car guy driving my son around. Its different if he is teaching him through a mutable hobby of racing go-go-karts on a track. I just think it was weird this guy had access to all this families personal vehicles to just drive around. I dont get it and I have my "rich and snooty" hat on, lol.
I am wondering if the assistant/driver drove Phillip around in the flashy cars, perhaps even back to his old neighborhood where Wint's family happens to live.