We have shady ornaments in my family!

It started with my siblings a few years ago. My sister had a mental breakdown in her second year in university and when her semester ended, she left the school for a while. She got a full-time job at the local bank with her free time. Once she had made peace with her breakdown and stepping out of school, we went to town with the jokes. All. The. Jokes. Christmas came around and I kid you not, my brother got her a plain wooden ornament and wrote, in sharpie, "CONGRATS ON DROPPING OUT OF COLLEGE TO BECOME A BANKER" and put it on the tree right in front of her.
Now whoever has the most memorable incidents (and are okay with being made fun of for them) gets an ornament subtly jabbing them. Guess what I'm starting with my friends this year >:D