In jail boss is an backwards acronym for Stupid Son Of a Bitch. Showing a lack of respect for people in charge, but gives the false sense of respect to the person in reference.
I don't know, but there was this kid in my 6th grade class that always used "boss" to mean dick. He would brag about his boss and the K through 5th graders didn't understand and asked him why he had a job. Once you entered 6th grade, you learnt the true meaning of boss.
- noun
1. oral sex.
2. A sarcastic or patronizing title for a person. the
term originates from the post civil war era of the
United States of America. Sharecroppers who were
once slaves noticed only few added freedoms after
the abolition. The term simply replaced the
title of master when addressing landowners.
3. A form of address often placed at the end of a
sentence to emphasize sarcasm or disdain.