Chicago Magazine asks various political types to weigh in on whether or not Obama should run. Very fun article.
Jonathan Alter
Columnist and senior editor, Newsweek
"Yes. He has to strike while the iron is hot. By 2012 or 2016 he will be just another smart senator and no longer a phenom. And even among African American politicians, he will no longer be unusual. Gov. Deval Patrick of Massachusetts and Sen. Harold Ford of Tennessee will be mentioned in the same breath as Obama, diluting his strength. By then he would also have made the inevitable enemies of 8 or 12 years in politics and have many more controversial Senate votes to defend.
"The big negative for 2008 is Obama's lack of experience. This would definitely be an issue, as it was for Abraham Lincoln, who ran in 1860 with only one two-year term in the House of Representatives. But skillful performance on the campaign trail would counteract that criticism. One becomes familiar-and thus ‘experienced'-with great speed
the crucible of a presidential campaign. But to survive the charge of lack of experience, he would have to be a natural candidate. Fortunately for him, he is. Beyond that, his biggest asset is that this country has always been focused on the future. That means less interest in going back to the Clinton-Gore years-and a greater interest in moving into the future with Barack Obama."
Markos Moulitsas
Founder, Daily Kos (liberal blog)
"It's too early for him to run in 2008, and the window is fast closing anyway. What would make best sense would be for him to run for governor in 2010, and then use that as a springboard to a White House bid in 2016. He's young; he's got time. The Senate is not the best springboard for a presidential bid, and a first-term senator in the minority doesn't have the record to make a compelling case for promotion."
Molly Ivins
Syndicated columnist and author of Who Let the Dogs In?
"Yes, he should run. He's the only Democrat with any ‘Elvis' to him."
much more at link.
http://chicago.godengo.com/Chicago-Magazine/December-2006/Should-He-Run/