Never understood how anyone could get this far with, essentially, nothing in the bank. That doesn't mean money. I vote for the "front man" hypothesis.
Me too. Whether his Harvard Law Review presidency, and the subsequent media attention it garnered, brought him to the notice of a (ahem, cough) "mentor" who boosted him to where he is now, or someone bought that HLR presidency for him, we'll probably never know. We just know that was Obama's first step up the ladder.
What I do know is that such breathtakingly meteoric political rises to the doorstep of national executive leadership simply do not happen -- at least not historically in Western democratic forms of government. Heck, they rarely even happen in totalitarian governments, either. However, they do happen in coups and other forms of shortcuts to political power.
The quick rise of John F. Kennedy pales in comparison to Obama's rocketship ride to the top. JFK at least served with distinction the in Navy during WWI. He was in the Congress for 14 years before being elected president: a U.S. congressman for six years, then a senator for eight. Besides, we know who was behind Kennedy's rise, his old bootlegger father Joe, former ambassador to Great Britain.