I watched closely when Obamacare was debated. If Obama had only had had the courage to pound the table and tell his democratic senators to get in line, maybe Obamacare could actually have worked. Instead it turned into a half assed attempt that was flawed from the start.
Same with the bank bailouts. He was in an excellent position to get some real change but chose to keep Geithner who gave the banks what they wanted. And a precondition for anybody who administered the bailouts was to have worked for an investment bank.