OKAY LISTEN UP IF YOU LIKE SUPERNATURAL AND JOHN MULANEY THIS IS IMPORTANT
So first here is a little timeline.
J.J. Bittenbinder joined the Chicago P.D. in 1971.
John and Mary Winchester got married in 1975
Dean was then born on January 24th, 1979.
John Mulaney was born on August 26th, 1982 in Chicago.
A fun and possible theory is that John Winchester was in Chicago and met Ellen Muleney in July of 1982. He was in Chicago for work and I believe he was doing some everyday thing and ran into Ellen Muleney and saved her life by accident. She thanks him profusely and he spends the day with her, to make sure she was okay since she was 8 months pregnant. Now, since John Winchester was so nice, Ellen decides to name her son (to be born a month later) after her lifesaver. John then goes back to Kansas where Mary gets pregnant that August with Sam.
That is a side theory, here is the real one.
I own John Winchester’s Hunting Journal that I bought at a book sale. I was going through the dates of 1987, where Dean would have been in 3rd grade. On May 17th, 1987, John W. writes in his journal “Already, I’m trying to figure out what to do about school in the fall. I’m starting to figure out that you can move a kid from school to school every month”. However, later on January 24th, 1988, (Dean’s ninth birthday) John W. writes “He’s (Dean) been in three schools already this year. Who knows how many more?”. So, this means that Dean had been to three different schools between September 1987 and January 1988, a mere four months. However, in these four months, we don’t have any intel on where the Winchesters were.
We know that J.J. Bittenbinder gave his assembly about “Street Smarts” in the 1980s (every year) and according to John Muleney, he heard this speech when he was 7 years old, the second grade. An assembly is given to the entire school, not just one class so it was an elementary school. Dean was 8 in 1987 (third grade, elementary school). Therefore, I can say, with almost certainty, that Dean Winchester attended a J.J. Bittenbinder assembly about Street Smarts and absolutely loved it.
You cannot tell me that Dean would not worship a man who told him how to stay safe and who wore a cowboy hat.
So the Winchesters were in Chicago in September of 1987.
Now, here is a little more. Dean would come home and tell Sam all about the Bittenbinder method and Sam would love it. Love it so much that he wanted to grow up to be just like J.J. Bittenbinder. Now, Sam “abandoned” the Wichester family to attend Law school. Now, why would Sam Wincerster want to attend law school? I believe that it is because Sam wanted to become a police officer like J.J. Bittenbinder but it was too similar to the family business, so he did the next closest thing, Law school. I also believe that the Bittenbbinder method helped Sam on at LEAST 1 LSAT question.