This is an older article, but it is such a foundational truth (IMHO), that it deserves a re-read. Or, a first read if you've never seen it.
@Sanguine Bill Bennett has made that same case time and time again. Years ago one of my uncles passed away leaving a wife daughter and very young son. He managed to get himself into quite a bit of trouble and ended up getting himself arrested one night. My Aunt called my Father to ask him to bail my cousin out, and my father said he would do that in the morning. My Aunt was pretty upset that her son was spending the night in jail. My Father told her she could have someone else bail him, but he felt a night in jail would do my cousin some good.