A President is only as good as his advisors. You get boxed into a certain way of thinking, depending on who's giving you the briefing every morning and doing all the nitty-gritty details.
This is probably what happened to Bush, who was surrounded by neo-cons and militarists like Cheney, Rumsfeld, Wolfowitz, and Feith. It's no wonder that we invaded Iraq.
This seems to be what is happening to Obama on economics. He gets an economic briefing from Larry Summers every morning, probably 5-6 days a week. Summers is his economic/financial guru. On other issues, Geithner is his go-to man. So virtually all that Obama sees/hears every day on financial or economic matters is what Summers and Geithner tell him.
So if Geithner is Paulson-lite, and if Summers is Rubin-lite, then what do you have? An Obama whose view of the financial world is aligned pretty closely with that of Wall Street. Add to that a certain leaning toward the 'Chicago School of economics', whose guru was Milton Friedman. Add to that a political centrism that seems natural to Obama. Add to that the huge political contributions from Wall Street. Add to that Raum Emanuel as Wall Street's favorite Congressman as least in terms of political contributions, before he became chief of staff. A perfect alignment favoring the Wall Street world view.
Now the odd thing is, when he is talking to the press, Obama says things that sound good to my ears. But then it rarely gets translated into policy. No surprise there, with guys like Summers and Geithner whispering in his ear.
I will venture to say this: the last thing Obama needs to do is to try and keep Wall Street happy.