For the first time, Sen. Barack Obama was playing defense with the press. It was after a get-out-the-vote rally on Monday. Instead of the usual fawning Washington reporters tossing softballs as they worked up adoring stories about him running for president in 2008, Obama was taking questions from the City Hall news crew about his astoundingly bad judgment.
They drove up to Waukegan to find out for themselves why on earth Obama had anything to do with the shady, recently indicted Tony Rezko.
WLS radio reporter Bill Cameron put it this way in the lead-off question: "What in the world were you doing in a real estate deal with Tony Rezko?''
For the next 14 minutes, Obama had what for him was a new experience: explaining himself in public for questionable personal conduct.
Obama's inquisitors were reporters who knew him for years and were neither awed nor intimidated by him. It was just another grilling of yet another Chicago pol who got caught in a sticky situation.
Put another way, Obama was being treated just like everybody else.
"This is the first time this has happened and I don't like the feeling,'' Obama said. "It's frustrating to me, and I'm kicking myself about it."
Book deal leads to real estate deal
To recap: Obama inked a book deal after winning election to the Senate in 2004. With his new wealth, in June 2005, Obama bought a $1.65 million mansion in Kenwood, some $300,000 below asking price. Rezko's wife Rita paid $625,000, the list price, for an adjacent empty lot the Rezkos may develop.
The deals closed the same day because the seller insisted both parcels be sold at the same time.
When the deals went down, Rezko -- who befriended Obama when he was a nobody Harvard law student -- was already cast in news stories as a controversial figure and political fundraiser.
By January 2006, when Obama bought a strip of Rezko's yard, Rezko's status was elevated to politically radioactive, since it was known he was under investigation by federal prosecutors.
The Rezko story broke last week, when Obama was wrapping up a national tour serving several purposes: promote his new book, The Audacity of Hope, raise money and stump for Democrats, and lay the groundwork for a possible 2008 White House bid.
Obama, in a written reply to questions submitted to him from the Sun-Times about Rezko last week, said he made a mistake and "I regret it."
He returned to Illinois to campaign Monday with Sen. Dick Durbin for Democratic House candidates Tammy Duckworth, Dan Seals and Rep. Melissa Bean.
On Sunday Obama was followed on a multi-state blitz by a team from ABC's "Nightline" for a segment on Monday night about the -- have we heard this already -- "star power" of the Illinois senator.
After today's election, Obama is going to more systematically consider a White House bid. Obama's inexperience is a factor. He told ABC's Terry Moran "I think the real question is: Do I have the judgment to be president, or do I have the vision to be president? Do I have the passion to be president?''
He added, "Do I feel like I possess the capacity to make good decisions on behalf of the American people?"
First let's contemplate whether Obama has the ability to make good decisions for himself.
Crowds cheer for Obama in '08
Obama, offering further insight into the Rezko deal, said Rezko was one of the friends he called for advice when the house he eventually bought came on the market.
"It turned out that the person who had renovated the house which I was interested in purchasing had worked with Rezko in the past, so that was the connection," he explained.
Obama said he had nothing to do with Rezko's eventual purchase of the land next to his house, and they were not negotiating together. He said he had no idea Rezko was offering full price for his land. Obama said he got a bargain -- $300,000 below list -- because his mansion was being unloaded in a "fire sale."
For the short term, the episode seems to have caused limited damage to the Obama brand. No national news outlets or influential blogs have picked up on the controversy.
Obama was treated with wild enthusiasm Monday at rallies in Waukegan, Grayslake and Elmhurst. While at the College of Lake County to boost Bean, the suggestion that Obama run for president brought the crowd to its feet.
So what did he learn from the Rezko transactions? Obama said, "One of the things you purchase in public life is that there are going to be a different set of standards, and I'm going to make sure from this point on I don't even come close to the line."
A lesson, on the road from the Kenwood mansion to the West Wing.