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.
IIRC the so-called "blue dog" Democrats in the House were the main obstacle preventing Obamacare from being more progressive. Unfortunately, they were right to be afraid...many of those Democrats lost their seats in the following years.
In retrospect the Democrats' window of complete control of the federal government was going to close no matter what they did (due to the GOP's obstructionism and unity in hating anything Dems did), and perhaps they should have passed more ambitious reforms while they had the chance.
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.