It's that he's not only from Chicago, but *succeeded* in the cesspool of what we will laughingly call "Chicago Politics" - what in most of the rest of the country (well, perhaps not Louisiana...I suspect folks there would mainly subtract points for a lack of style and failure to think big enough when it comes to corruption) would be recognized as corruption, bullying, backroom deals amidst smoke and mirrors, and generally all those elements of mid-19th century politics that much of the rest of the country has striven to distance itself from.
To succeed, Obama had to be *better at that game* than the rest...and in his case, farther left. I could tolerate the leftism better if not for the stench of the Chicago machine.
Now Obama must face meaningful political opposition with big stakes for the first time in his career, after the loss of the Dem. super-majority in the Senate last night. Let's see how he does - if he continues to listen to that high priest of the Chicago Machine, Rahm Emmanuel - or if he listens to common sense and begins to moderate his tactics, techniques, and goals.