You’re so 1988 or When did Barack Obama meet Bill Ayers?

UPDATED June 7, 2008. Note I will be discussing this crucial question with John Batchelor on his WABC radio show SUNDAY at 8:30 PM East Coast time. You can tune in on the web here.

This has remained until now an unanswered question. Yet it is crucial to the still unanswered question about the influence today of the authoritarian “leftists” Bill Ayers and his wife Bernardine Dohrn on the Obama campaign. A recent New York Times profile of Obama’s days on the South Side of Chicago contends that, according to unnamed “aides” to Obama, Obama first met Ayers and his wife Bernardine Dohrn at the Hyde Park home of the couple. This meeting occurred apparently in November, 1995 according to an anonymous blogger who claims to have been there, as Obama was launching his campaign for the state senate of Illinois.

If the Ayers/Dohrn-Obama meet and greet took place in November, 1995, it cannot have been the first time that Obama met Ayers.  By that time Obama was already Chairman of the Board of the $50 million Chicago Annenberg Challenge Grant program that was designed by Ayers. Ayers began the grant proposal design process in December 1993 and the grant was formally announced in January, 1995.  Barack Obama was identified as the Chair in press reports in June of 1995.
So, unless Ayers helped pick a board chair he had never met and would never meet until the “meet and greet,” Obama, in fact, met Ayers well before the launching of his state senate campaign.  Of course, it is very likely that there would have had to have been a very close working relationship between Ayers, as the lead architect of the Annenberg proposal, and the first board chairman.  They would have had to have agreed on basic educational policy issues. And Obama would have been crucial in leading fund raising efforts since the $50 million grant was conditioned on a 2-1 match from other donors (and something they were quite successful at – raising an additional $60 million by 1999).
As I have written here before, my hypothesis is that Ayers and Obama had an older relationship and a deeper political affinity than has been made clear until now. The attempts by so many around Obama, and by Obama himself, to portray this as an arms length relationship simply do not fit the facts that are available. 
For example, the Annenberg Challenge grant money was aimed at solidifying the school reforms put in place in Chicago in 1988 when a campaign for “local control” emerged in the wake of a teachers’ strike that galvanized business and community opposition to the power of teachers’ union and the Chicago school bureaucracy. 
Both Obama and Ayers were active in that reform post-strike campaign. Ayers, deeply active in the reform effort in 1988, became chair at some point (I do not know when) of a major force in the lobbying for that 1988 campaign, the Alliance For Better Chicago Schools, or ABCs.  The Developing Communities Project which Obama headed at that time was a member of the ABCs, apparently one of the few members of the ABCs that worked with the black community. Many in the black community knew that teaching, the unions and school administration were one avenue to the middle class for blacks and thus were wary of the reform effort. A leading entity responsible for organizing the ABCs was Chicago United, a multi-racial business group, founded by Bill Ayers’ father Thomas Ayers.  
Certainly support for “local control” would have been a pre-requisite to allowing Obama to chair, at such a young and untested age, the Annenberg Challenge. Thus, I think we can safely date the beginning of the Obama-Ayers relationship to at least 1988 when the reform effort was underway in Chicago schools. That was also when Ayers and Obama would have met up with the future Executive Director of the Annenberg Challenge, who would have been hired by Ayers and Obama, Ken Rolling.  Rolling in 1988 was on the staff of the Woods Fund which provided several grants to the school reform effort and to Obama’s Developing Communities Project at that time.  Of course, a decade later, in 1999, as is already widely known, Ayers would join Obama on the board of the Woods Fund itself.