Model work brother

I’m not seeing how my results prove my thought in the following model, involving my brother who is self employed, owes the IRS and his x-wife money, and overspends, and has been in this same situation number of times over the past 15 years. I, thanks to Dave Ramsey, am generous with gifts but no longer loan money to family. Yet they keep asking. I would like to help him somehow.

C: He is out of money and ask me for a short term loan, until the next case settles
T: he’s awful at managing money
F: mad
A: spend a lot of time trying to figure out, once again, another way to say no and that he is not taking responsibility for his actions, as well as try to figure out how to help him–should I once again offer to pay for the Dave Ramsey course, wonder is there some other way to help him see the light?
R: strain on our relationship, resentful for my time and energy being spent on trying to solve it for him