+20 Taking care of family when one sibling has history of poor decision making
If you were to win Mega Millions and want to take care of parents and two siblings. One siblings has a history of poor decision making - nothing bad like jail. But constantly between jobs and really bad with money, history of drug/alcohol use etc.
You’d want to make sure they are set for life but at the same time don’t become a textbook example of money ruining everything by allowing them to be enabled.