...no, I'm kidding; Chicago is a mess because of the Daley machine, not because Obama was a "community organizer" there. Chicago is a mess because it's been run by Democrats for about a thousand years with absolutely no reason for Democrats to fear being replacemed by adults.
But the problems that the Obama administration has faced during its transition are legion--if he had been a Republican many elements of the press would already be referring to it as "the failed Obama administration".
Geithner couldn't even manage to do his taxes correctly; he couldn't recognize his own incompetence in this arena and hire a professional. (Hell, he could have gone to H&R Block!) Now Obama expects him to manage the Treasury--and the guy can't even buy help. This probably means that the people Geithner wants to hire are smarter than he is, and realize that having your name attached to a sinking ship is not wise: at that level, even failures that are beyond your control count against you.