Trying to follow

What I saw on my Friday night bike ride:
-the last five seconds of a dinner concert at Belmont (I think for the new freshman)
-the Vanderbilt Girls soccer team beating some other team 4 nothing before half
-The beginning stages of some frat parties
-The Parthenon without much of anything going on
-Lot’s of live music on Broadway
-two college age guys having dinner with two gentleman who appeared to be homeless
-a gentleman handcuffed outside a bar while another was being written a ticket by a police officer.
…and that’s about all I had time for.

This morning I was driving in traffic and I noticed the gentleman behind me in my rearview mirror. He was probably in his late 40’s, white, dressed in business attire, and in a nice car. Outside the window there where 4 teenage boys, African-American, dressed in throwback jersey’s, baggy and sagging pants, on their way to school.
The gentleman in the car was starring intently at them obviously contemplating something in his head related to the scene before him.

What was he thinking?