It is no secret that I have serious reservations about Barack Obama’s lack of experience and questionable judgment. And, until recently, the media avoided doing hard hitting pieces on the good Senator. Well, it appears that the main steam media finally is starting to ask some questions that should have been raised months ago. Consider Barack’s stance on Afghanistan. For almost a year, Barack has been pretty clear about the policy he would pursue. During a speech in August 2007 at the Woodrow Wilson Center, Barack said:

It is time to turn the page. When I am President, we will wage the war that has to be won, with a comprehensive strategy with five elements: getting out of Iraq and on to the right battlefield in Afghanistan and Pakistan; developing the capabilities and partnerships we need to take out the terrorists and the world’s most deadly weapons; engaging the world to dry up support for terror and extremism; restoring our values; and securing a more resilient homeland.

As President, I would deploy at least two additional brigades to Afghanistan to re-enforce our counter-terrorism operations and support NATO’s efforts against the Taliban. As we step up our commitment, our European friends must do the same, and without the burdensome restrictions that have hampered NATO’s efforts. We must also put more of an Afghan face on security by improving the training and equipping of the Afghan Army and Police, and including Afghan soldiers in U.S. and NATO operations.

We must not, however, repeat the mistakes of Iraq. The solution in Afghanistan is not just military — it is political and economic. As President, I would increase our non-military aid by $1 billion. These resources should fund projects at the local level to impact ordinary Afghans, including the development of alternative livelihoods for poppy farmers. And we must seek better performance from the Afghan government, and support that performance through tough anti-corruption safeguards on aid, and increased international support to develop the rule of law across the country.

So what is the problem? I think these are sound positions. However, if Barack genuinely believed what he was saying, why did he not use his status as the Chairman of the Senate Foreign Relations subcommittee on European Affairs to examine the validity of using NATO in Afghanistan?

This is not a bullshit question. The U.S. decision to turn to NATO to help us out in Afghanistan was old news by the time Barack became chairman in 2007. NATO started ramping up troops in Afghanistan in December 2005. When January 2007 rolled around Barack was in a unique position, by virtue of his chairmanship, to do a series of hearings that, for example, on the challenges facing the United States in Afghanistan and the viability of relying on NATO. But Barack says he was “too busy” running for President.

Sorry, but that is a lame excuse. Are we expected to believe that he was incapable of putting together at least one hearing that would have helped burnish his limited foreign policy credentials? This is more than a tactical mistake. For me it is a question of his judgment and his political vision. This smacks of someone who is so intellectually lazy or incurious that he failed to recognize the opportunity dropped into his lap. He wants to run for President. Foreign policy issues are a critical part of the upcoming campaign. And what does he do to bolster that part of a thin resume? Nothing.

Unfortunately, this flaw in judgment is not isolated to his failure to hold a hearing. It appears to be a consistent theme in his political life. He has more than a passing friendship with an unrepentant terrorist, William Ayers. And he goes into a questionable real estate deal with one of his political supporters and fundraisers, Tony Rezko, when Rezko is facing imminent indictment on Federal corruption charges. Folks with sound political instincts would know to avoid these kind of situations. It looks wrong and in politics perception matters.

But Barack’s problems, particularly with Rezko, go beyond a simple matter of perception. CNN identified some of the looming pitfalls (view youtube here).

And this Rezko problem in all likelihood will get worse for Obama in the coining weeks. Tony’s trial starts on Monday. He’s up against Patrick Fitzgerald. Fitzgerald already has sent a former Illinois Republican governor to jail on corruption charges. He also beat a massive propaganda campaign in Washington to exonerate Scooter Libby and convicted him on perjury and obstruction of justice for his role in outing Valerie Plame. Fitzgerald is not likely to fail.

Rezko does not have George Bush behind him with a tacit offer of a pardon. Rezko does not have a group of prominent Washington and political luminaries willing to make excuses for his crimes as did Scooter Libby. Rezko faces significant fines and jail time. A man under that kind of pressure will have no second thoughts about throwing other people under the bus. Senator Obama, who received hundreds of thousands of dollars from Rezko in his previous campaigns, who had a real estate deal with him, who intervened on his behalf on government matters, is very likely to get dirtied up in this trial. As the political season enters June, the American people may be asking the question, how venal is Obama?

I do not begrudge Barack his ambition. He is a shrewd politician. But I also see a consistent pattern of flawed judgment. Not holding hearings on what NATO could or should do in Afghanistan and buying property with a guy who is the target of a Federal corruption probe are radically different issues but reflect the same lack of sound judgment. Obama’s questionable judgment on these issues outweigh his 2002 opposition to the war in Iraq in my book.

Regardless of what happens in the upcoming Tuesday primaries, these issues will not go away. And as the public learns more about the real Barack Obama, the bloom on his rose is likely to fade and fade dramatically.