Every once in while while I am at the 7-11 by my house I catch a sighting of Winnetka man. I have in my 24 years seen many types of crazy homeless people, and even on semi sub conscious level categorized them into groups, as I think we all have, just automatically. Types if you will. Winnetka man does not fall into A type.
Something snapped in Winnetka Mans mind one day and though he went off the rails mentally everything about his appearance remained the same. As far as I can tell, this happened roughly two years ago, I can only gather this because Winnetka man remains incredibly physically fit for a homeless person. The best way to describe him is like an even taller Jerry Seinfeld. And he has the personality too but we’ll get to that later in the analysis of this interesting specimen.
Winnetka man also apparently had lots of money at some point, this is gathered by the watch he still wears and the clothing he has which is fitted but heavily dirtied from homelessness. He’s also physically fit, the sort that payed for a personal trainer for at least one full year and stuck with it. Also it appears to be the case, Winnetka man looks like he did something important at some point two years ago, then he snapped and now he is demented in an always playful way.
Like his brain was switched with that of a golden retriever and he just wants to have fun at 7-11 and no matter how much they yell at him he thinks they are trying to play with him.
It doesn’t just seem that he did something important, Winnetka man is intelligent. Winnetka man recites things he could have only learned from expensive sources, full texts of law that nobody within probably 10 miles except me and himself know. We would probably get along swimingly. It’s hard to find people who read full texts of the law, those people usually also have opinions and so the conversation begins. However Winnetka man is insane, and I do mean insane. His eyes do not change from one mode, which is fully open, and he is never not smiling. He’s like the Joker from Batman, or like that cat from Alice in Wonderland but in a more adult themed version of it.
So it’s very interesting. Winnetka man rarely stays for more than 5 minutes, he did something very bad to the Indian once and now when he comes in the Indian yells “get out you motherfucker” with such a strong indian accent that I thank God someone taught this man the word motherfucker. Winnetka Man does not get scared, Winnetka man chuckles, playfully, not obnoxiously. It appears Winnetka man is living in a world where this is all a game, a video game before his eyes but with infinetly more possibilites. It’s very creepy and interesting to see. The Indian only has two sentences in his reserve, he’s an 50ish guy with glasses that is pissed off at life in a little red vest. His first sentce repeatedly yelled probably about 9 times is “Get out you motherfucker”, to this Winnetka man says” comon, give me the beer for a dollar” all the whilst smiling heavily and backing towards the door, he’s left the beer on counter, this is all just fun and games to him. Winnetka. By the way, the beer is actually only a little over a dollar, it’s Rolling Rock and it’s a tiny amount and it’s perfectly okay for when you want something watery. I don’t think Winnetka man has any dependencies, not to drugs or to alcohol. I don’t think Winnetka man craves that beer or anything else. Winnetka man is very interesting and so I am still exploring theories about him. Because it does not seem he is driven by anything in particular. He never changes from that smile like some kind of a smiling zombie, his face never changes to a surprised, shocked or scared look. It’s a very odd thing to see.
The best I can tell Winnetka Mans mind has gone into perpetual state of playful anarchy at the age of 40 something, he went and transformed from successful money making executive/something or other to a beach bum over night and decided to try and mesh the two styles, because fuck it. Why not.