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He failed at running his first big venture - casinos - despite the money his wealthy father poured into it. At one point, his father sent his driver to purchase over $3 million in chips (with no intention of gambling) and ended up having to pay thousands in fines to the gambling commission since it's against the rules to lend money to a casino without a license. He then sold his father's entire lucrative business at a loss both because he needed the money and selling it in its entirety to a single buyer allowed him to avoid the attention - and paying taxes. His whole life has been a series of failures, initially propped up by his father. And there were voters who actually trusted him to run the most powerful government in the world?? 
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