When I was in college and working construction, I worked with a few less savory characters. One guy who was steady on the job but had addiction issues (According to my boss, crack). He was high/drunk once and lost a bar fight. He was angry enough about it that he threw a molotov cocktail at the winner's porch, and went to prison for a few months, followed by either probation or parole, and he came back to work with us.

Part of the conditions of his release was that he had to stay clean.

Week 1: His parole officer didn't test him
Week 2: His parole officer didn't test him.
Week 3: Failed urine test. Back to prison. Never saw him again.

Another guy was just a blue-collar young guy who worked construction during the day and did club security at night. He got pulled over for 100 mph in a 55 mph zone in downtown Wichita, on the US 400 bridge over the river. So, charged with reckless driving. Whatever his bail was, it wasn't enough to make him face the music because he came back to work for 1 day to tell us what happened and that he was going to flee the state. Never saw him again.

Added another:

Third guy was a small dude who always smelled bad - sickening sweet. I don't think I ever saw him at work sober, and he was very thin - apparently he chose alcohol over food. As far as I know, alcohol was his drug of choice. He was pretty functional, but weak. Because he never ate, maybe?

One day my boss asked us to carry roof trusses from the pile on the ground to the 2nd floor and lay them on top of the walls so that we could stand them upright later. A lot of times this is done with a crane but cranes are expensive and there were only 25 or so of these trusses.

So he had a ladder on one side of the wall, I had a ladder on the other side, and we each took the end of a truss to the top of the ladder and heaved it up on the wall. The first trip he did fine. The second trip he needed to rest once half way up. The third trip was the same. The fourth trip he needed TWO rests on the way up. I imagined him losing his grip on his side and the entire thing swinging down and sweeping my ladder out from under me and went to the boss and asked to be left alone to do it myself. My boss fired him immediately and I did the rest of the trusses by myself with the ladder in the middle.

As far as I know he never had much interactions with the prison system, but I didn't know him very long.