Chicago Sun-Times
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Sweet column: Obama, what was he thinking.


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.

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Second time I'm emailing this. Evidently you didn't receive the other. Lynn, Obama's problems will not be the Rezko's of the world. His problem will be Hillary Clinton. If he considers a run for president, the 'Golden Boy will be turned into Tin." When Clinton's people get done Barack will be a nobody. Its already started. Maureen Dowd of the NY Times and a big friend of Hillary's has already began questioning the senator's past. As have several other eastern writers. Why even Michael Sneed mentioned Obama's $million and half dollar home and his wife's penchant for expensive mink coats. Hillary's crowd plays hardball. Why she spent a record $29.5 million on her senatorial re-election, a race where the result was a long drawn conclusion long ago. She isn't going to allow anything in her path to the nomination. Realize that folks. And Obama will be smeared even on things he may be innocent. Lynn, you allowed to print this?

Hi Ms. Sweet,

Just wanted to comment on your story concerning Senator Obama.

It's not like he didn't think he would continually get the adoring praises of him forever. He knew this day would come. I have to agree, it was poor judgement on the part of Senator Obama and appearance does means a lot. I'm sure he's learn a very valuable lesson. But, I'm sure you and your colleagues will constantly remind him of this episode in his life, right?

Anyway, I was curious as to why you and other reporters, in the printed news and television didn't write one column regarding the scandal, that plague Atlanta's former Mr. Campbell and NBC's Marion Brooks. Now here was a woman who displayed great lapse of judgement! But yet, the public is to trust her judgement in reporting the news.

Ms. Brooks was the mistress of Mr. Campbell for nearly two years, where she received cash and gifts and a paid apartment to boot. She was also allowed by her bosses in Atlanta to report news coming from Atlanta's city hall, even though many of her colleagues knew of her involvement with the mayor.

You're a political reporter. Why didn't your write about that? Don't bother to answer either one of those questions. I already know the answer as does the remaining newspaper readers; It's called protecting your own.

I'm still a big fan of Senator Obama and I'm sure with time, he'll be a stellar public servant.

Marcia Williams


Just so you know, I got my news information about the Campbell trial through the Internet. And the print news publishing companies are wondering why their readership is dwelling. Amazing, isn't it?

Dear Ms. Sweet:

I know you must be getting tons of e-mail and/or other communication about your column today. I write not as an Obama fan, which admittedly I am seemingly along with the rest of the world, but as an advocate for fairness in media reporting.

My question is, how could Obama have been clairvoyant enough to know Tony Rezco would come under investigation, and then indictment, years ago? In fact, I was even surprised to see Obama admit to any bad judgment. Isn't this just 20/20 hindsight? And it certainly seems that the media (local, at least) is desperately looking for a chink in the armor of a heretofore teflon politician. As my nemesis Bill O'Reilly says, "Tell me where I'm wrong."

Rezko was considered controversial --well known in political circles--by the time Obama talked to him about the house.

Who really cares that he bought a piece of land. There is nothing wrong with what he did. He didnt get a shady price for it, or anything that would say he is corrupt. SO BIG DEAL he bought some land. Get over it.

News and comments are all dated November 2006. Why, in 2008, in the middle of the campaign, nothing is being reported on Obama's bad judgment. The only thing that is reported is what Obama constantly repeats on the campaign stump, i.e. Hillary's bad judgment in voting for the war resolution. There is no way to determine whether Obama would have voted against Bush's war resolution. He was not in the Senate at the time. While since serving in the Senate, Obama has had the opportunity to vote against the war. Instead he continually votes to fund the war. Isn't that a contradiction?

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Lynn Sweet

Lynn Sweet is a columnist and the Washington Bureau Chief for the Chicago Sun-Times.

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About this Entry

This page contains a single entry by Lynn Sweet published on November 7, 2006 8:23 AM.

Ground game rules. was the previous entry in this blog.

The Obama Chronicles: Waukegan interview transcript. On Rezko, mistakes and being held to a high standard. is the next entry in this blog.

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