Huge update to my story. I feel it's important, so I want to put it here for opinions.
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Friend: Going to HR over my boss' head is a bad idea. Also, going to my boss directly is bad. This division of the company is only a three person team, and my boss is one of those people. As such, there is no such thing as an anonymous comment.
Me: So you don't trust that your boss will keep it to himself unless something else happens? That way you're covered?
Friend: He can't. If he mentions anything at all to my coworker, he'll know right away that it was me that said it. Also, this is someone that I'm going to be dealing with for years, outside of work. So it's not like he'll be gone as soon as the job is over.
Me: I understand. But at the same time, he doesn't seem to have the same regard for you. He's openly tried to get you fired in the past. So he clearly doesn't give a shit that you're someone he will see for years in the future. So why should you?
Friend: It's because he doesn't have to. He has the power in this "relationship". Here's some back story. My mom doesn't work. And her welfare checks no longer covered her living arrangements, and her house was foreclosed on. This guy went out and bought it, so he's now her landlord. Until I'm able to move her somewhere else, that is. So it's a situation where either I play nice with him or she's out on the street. This guy did something vaguely similar to a friend of mine a couple years ago. He loaned him some money and then basically used that as leverage over her for years. Actually, he still may be doing it.
Me: I didn't know that at all. All the more reason to fuck this guy and get your mom out of that situation.
Friend: Rock and a hard place. The solution to that is to move her away, but I can't afford to pay for her rent and she isn't willing to work herself, and her welfare check won't cover it. So as a result, moving is off the table for now. This also means that getting out of this situation isn't an option for me.
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Ok, what does he do in this situation? Is there anything he can do? His goal is to finish school before going full time. As such, he can't afford to pay for his mom in addition to himself on his current wages. This is the same guy that I talked about before that had the job that wanted to offer him x to work full time, but he chose to go part time and complete school instead.