Couple years back I had the option of playing in a walking 5-some at a well-known national club in SC, but with about four hours of sunlight left and a half hour drive to a yet unseen hotel, I opted to jump ahead by myself. This presented a problem for the caddies, who, apparently, had the game already handicapped. Nonetheless, my assigned caddie broke off with me, and we had a very entertaining late afternoon.
Paul described himself as a scratch golfer who caddied to feed his gambling habits, which were, by then, under control and limited mostly to golf. He played the local mini-tour circuit and other high-stakes games throughout the Carolinas, all the way down to FL. He definitely knew how to read greens and did an excellent job of guiding me around the course while playing at a moderate pace that didn't push the members ahead of us.
As the round unfolded, we delved into various subjects of common interest- GCA was not high on his list, though he had strong opinions on how different courses tested his game- including our backgrounds, education, politics, etc. Paul noted that his life experiences were unusual in that his dad was a well-known member of an organized crime family in the NY/NJ area, and that he grew up in the business. He had married a Jewish woman from a reputable family on the good side of the tracks, both expecting that they had hit the jack-pot, neither realizing that both families were flat broke (his dad was on the way to jail for an extended period; his in-laws were nursing a longtime failing business).
A recovering alcoholic who had some past experience with drugs, Paul never completed high school and, allegedly, made a good living early in his life gambling and as a bookie- horses, sporting events, cards, golf. Though he claimed to never having ties to the mob himself or dealing drugs, he said his life changed for the better after being stopped by the police on a traffic violation in NJ and a search of his car yielded a paper bag with over $100k cash. He said that he wasn't headed to a drug buy- that he had just won the money at a private poker game- but apparently he was being watched and they had enough evidence to put him in prison for a number of years (I gathered that it wasn't the first time).
Shedding much of his past life including his former wife, he was living with a local woman in a modest home nearby, golf and his new family providing the needed direction. During his time in the Pen, he developed a love for books and particularly enjoyed biographies and learning about economics. To my great delight, he was fully conversant on Friedman, Sowell, Hayek, Bastiat, and had even read Wanniski. He knew all the Supreme Court justices, their proclivities, and how the Fed and the monetary system work.
About the only thing Paul said that I thought was suspect had to do with a pushed tee shot which barely rolled into a large lake flanking the right side of a hole on the backside. Before I could rake the ball out of the water with an iron, he yells at me to leave it. Apparently, a caddie had lost his forearm to a 10'+ alligator retrieving a ball near the same spot earlier in the year. I've done a Google search and have been unable to verify his story, but I tend to believe him.
I have played golf with any number of individuals with post graduate educations and I can't think of a single one who left a more lasting impression in such a short time than Paul. We had an amazing three plus hours together, and consider the $100 caddie fee a relative bargain.