I, sadly, have to nominate my parents for the wall of shame. :(
My mom was dirt-poor Oklahoma Great Depression-raised. My dad was relatively wealthy (family had today's equivalent of $50M or so), also pre-Depression.
Neither of them could hit their ass with either hand.
Both were CPAs, making good money (I remember they were in the $90k range even back in the mid-1970s, which was a handsome sum back then). We lived in an 1893 house which was absolutely falling apart. Y'know the spooky abandoned mansions in horror flicks? Worse. I'm not kidding even a little bit. We never - and I mean NEVER - had people over to the house.
Perenially at risk of having the utilities turned off. YEARS behind on property taxes. Bankruptcies. Untold bounced check fees. Driving utterly unreliable garbage for cars. My mother would save everything except money. There were pathways through the house, and parts of the house were blocked off so that we didn't fall through the rotten floors because of the roof. No A/C (in Texas, mind you).
To this day I have no idea how they went through so much money and had nothing left. My mom gave away money right and left, and we ate out constantly, but other than that, I'm flummoxed.
To nobody's surprise, I turned out to be the retirement plan. Dad didn't live long enough, but my mom did. I bought her a small but nice little house, covering the utilities and taxes. She absolutely ruined it. I was stressed every time I went over and there would be crap everywhere, feral animals she let in my leaving the windows open, roaches, and filth.
Eventually, after a few years my breaking point came. I found that she had filled the garage with pallets [!!!] of 80-gallon propane tanks "just in case." There had to be 2,000 gallons of propane in the garage of this residential neighborhood, alongside drums of gasoline, kerosene, flour, rice, cooking oil, and the list goes on.
Now, if this place had ever caught fire, the firemen rolling up would have no idea what was inside. Neither would the neighbors, who I'm sure would gather to watch. That propane would have leveled the block, killing who-knows how many people. Guess whose name was on the title to that property?
I told her point-blank that the gravy train had left the station. I refused to place myself at that kind of risk since she couldn't be trusted. She initially refused to leave, so I sold the place (upside-down because of condition) right out from under her. She moved in with like-minded friends out in the country, taking all of that stuff with her. When she died, as executor they asked what I was going to do with all of her stuff. I looked them right in the eye and said that they must be mistaken - my mother didn't own anything, and they must be confusing it with the property owner's things. They were absolutely gleeful, and so was I.
That was a VERY expensive lesson learned. It wasn't the first time, but it was dang sure the last time that I would be a piggy bank for someone else's bad decisions, no matter who they are.