I will make now a prediction about one thing we will see in the event of an Obama Presidency, and stick by it: Obama will never be free of his past.During the 8 years of the Bush presidency, we have heard relatively little new information about his pre-presidential career, with the exception of the 2004 effort to dig further into his Texas Air National Guard service to contrast him with John Kerry. There's a reason for this: when Bush ran for President in 2000, the media crawled all over whatever they could find, most famously culminating in the story of his 1976 DUI arrest that broke the week of the election.
Much the same was true of Ronald Reagan and George H.W. Bush. The press dealt mostly with their tenure in office, having already fully vetted them prior to their elections. We have seen in recent months the same process for Sarah Palin, with every aspect of her life being turned over by investigative reporters. And of course, John McCain as well.
Contrast the Clinton Administration - during the Clinton years, we had a steady stream of stories, often starting either with legal processes or with reportage by conservative media outlets, bringing us new information about the Clintons' past, ranging from Hillary's 1978 commodities investment (which was fully concealed during the 1992 campaign by concealment of the Clintons' tax returns) to the ins and outs of the Whitewater investigation to Paula Jones and Juanita Broaddrick to things like the Mena airport saga that came out gradually.
Not all of the stories about the Clintons' past were blockbusters (the Mena story never amounted to anything that really connected all that directly to the Clintons), and obviously the credibility of the he-said-she-said stories of women like Jones and Broaddrick remains in the eye of the beholder (as for Whitewater, the New York Times did a single story on it during the primaries in March 1992 and then promptly dropped the issue). But voters should have had the opportunity to evaluate them before giving Bill Clinton the job, and certainly would have, if he'd been a Republican; and if the media had done its homework, these would all have been old news by 1993. The most egregious case was the commodities deal, which came out in 1994 (see here and here), and which probably would have been the one scandal too many to sink Clinton if it had been properly ventilated at the time. Obviously some of this was due to concealment by the Clintons rather than just media lassitude, but politicians don't get a pass for concealing things if the media wants them dragged out.
Anyway, that said, I will predict with great confidence that if Obama is elected, we will not by a long shot have heard the last of new information about his past in Chicago politics. So much of Obama's early years remains a cipher, due to the destruction of his State Senate papers, his refusal to release scores of other types of documents (as Jim Geraghty relates here, here, and here), to say nothing of the many "missing witnesses" (noted here) who can't be located or won't speak to the media. All those dams can't hold forever. While Republicans and conservatives will, if Obama wins, have plenty to do exposing his activities in the White House, at the end of the day, Obama's past remains a fertile field with many areas of investigation that have yet to be exhausted. We will not have heard the last of it. He will carry his past in the White House like Jacob Marley's chains, precisely because the media has not made him face it all on the trail.