JOHNNYBBAD bbm, I totally agree that "an extension of an earlier plan" is in the making.
If I wanted to escape jail, the guards are most vulnerable during "transporting the suspect/criminal/inmate" (choose your own descriptive word for Jake) to and from the courthouse or other facility (such as a hospital). In the transportation process, they are no longer behind cold walls, freedom is literally a car window away and they are seeing their community (the one they know they will never walk free in again for decades or longer).... the only thing that stands between them and freedom are two guards with no back-ups and no alarms. I can only imagine what must be going through a perp's mind during that process. I think it is a very dangerous time and situation.
If I were hoping/planning an escape:
I would ask for no restraints in the courtroom.
I would ask if I could wear regular/street clothing.
I would smile, act respectful and be cooperative. (But probably couldn't hide my smirk.....as each step of my plan falls into place.)
I would be thinking, it is better for me to "go down fighting" than let this court system ruin my future.
IMO, "something about to happen" is more a reality than a prediction. Always great to read your common sense posts.