He's either the dumbest person alive, or his life is so shitty he thinks jail is a better option. Hell, jail is my "fall back" retirement plan. Free room, free clothes, free food. Free healthcare (which is a HUGE plus late in life).
Too many benefits to ignore.
I can't wait to see what happens when millions of boomers with little or no retirement funds figure out that jail has some pretty solid benefits. You might take it in the ass occasionally, but hell, life gives it to most people up the ass on a regular basis so no big change there.