A Republican strategist speaking on the condition of anonymity reacted to the Caldwell comments by telling ABC News: "My advice to the Obama people: 'proceed with extreme caution.' They don't want to get into a discussion of character and background. They are opening a door that they will not be able to close. They are putting on the table issues and personalities that they do not want to discuss."

Asked which personalities? The GOP strategist cited the Rev. Jeremiah Wright, Tony Rezko, and former Obama law partners.

Now I don't think anybody believes the McCain Camp is not going to bring up Rev. Wright, it's not a question of "if" but "when".  What about the Obama camp bringing it up themselves?  That way they control more of the story, as opposed to letting the McCain camp decide when to play it as an issue.  Because if you are hoping the McCain camp won't "go there" you are incredibly naive, and if you are waiting for him to play it, don't expect it until late October. 

Wouldn't it be better getting it out of the way as an issue now?  So it will lack the election day bite the McCain camp hopes it has by releasing it days before voting day. 

Ideally it would have been best to bring it up during the Olympics, but the media would have seen through that.  So going forward, when would be the best time? It would have to be post Dem Convention, but before the first debate.

What about during the week of the GOP convention? Still too transparent? Would that be giving too much of a potential bump to McCain?

When would be the best time?

Also how would you go about doing it? Have a speech titled "Reverend Wright, Tony Rezko and Bill Ayers" where he talked about each in length and depth?

I assume Obama will be asked about Wright tomorrow at the Rick Warren summit.  Maybe that could be the impetus for another address down the line

Or leave McCain to play the Rezko and Ayers card because you have the Keating Five and Liddy/Abortion Bombers counter attacks if necessary. 

Now McCain does have a Pastor problem of his own in Rod Parlsey and John Hagee.  However even the staunchest Obama supporter has to agree it's not nearly as damning as Rev. Wright is for Obama.  I think the best way to use Parsley and Hagee against McCain show him as using their endorsments as baldly political.  Using religion as nothing more than a tool to help him win an election.  

If Obama gets out in front of the Reverend Wright issue and plays it when he chooses to and on his own terms he really could mitigate the damage.  He could simply say he wants to address Reverend Wright to the much larger GE audience and get it out out the way.  It would take a huge bullet out of the McCain arsenal and at best Obama could get credit for bringing it up himself. 

So whaddaya think?  Good strategy?