How Did Jackson Use The Regalia

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I believe that yes in a way Jackson was using the Regalia as an excuse to get money. Every time Jackson would receive money instead of saving it he would go and spend the money. Not only did Jackson spend the money on him, but he would treat other people to breakfast and shots at the bar. Putting myself in a homeless persons shoes I would try and get money anyway I can. Personally I would rather eat or have somewhere to sleep before saving my families history if I was homeless. Also trying to make 999 dollars in a day is unrealistic so why save the money. I would wait until I am on my feet and then try and save my grandmothers Regalia. I don't feel like Jackson tried to make people feel bad for him. I feel like he did not want to be a burden