Picking Apart Obama's Stock Portfolio

Editor's note: Nat Worden sat down with Wall Street Confidential's Gregg Greenberg to discuss the making of this story. Click here for the Webcast.

If presidential candidates were stocks, then Sen. Barack Obama might be the quintessential momentum play.

The young senator from Illinois stands as the current rock star candidate for the White House in 2008. Unlike his rivals, who are longtime fixtures on the national political scene, his reputation is pure. So, like a trendy new stock that is soaring on wings of speculation, either Obama can flame out under a long-term dose of public scrutiny or he can deliver enormous returns to believers.

A look at his recent investment record reveals that, like his supporters, Obama has a taste for betting on long shots. But two such bets placed in 2005 raise questions about the senator's judgment when it comes to buying stock in companies that are in line for federal funding. ...