164 Barack H. Obama: The Unauthorized BiographyOBAMA’S BIG BREAK: AYERS AND
THE CHICAGO ANNENBERG CHALLENGE
Diamond stresses that getting tapped to head up the prestigious and massively funded
Annenberg Chicago Challenge – based on no visible qualifications – constituted Obama’s key
inflection point or career take-off. Diamond is of course attempting to explain this process based on
more or less chance encounters among individuals, rather than being aware that we are watching an
intelligence network which goes back well over half a century. Obama and the Ayers clan came
together not by chance, but thanks to the fine Trilateral hand that fosters some careers and strangles
others. Diamond recounts: ‘Then, in late 1994 or early 1995, Obama made what I think was
probably the key move in his early career. He was named Chairman of the Board of the Chicago
Annenberg Challenge, a $50 million grant program to funnel money into reform efforts at Chicago
schools. It turns out that the architect of the Annenberg Challenge was Bill Ayers, who designed the
grant proposal and shepherded it to success. The purpose of the program was to defend the
controversial and troubled local schools council effort that had been put in place back in 1988. The
first Executive Director of the Challenge was Ken Rolling, who came there from the much
discussed Woods Fund (where he had been a program officer). The Woods Fund had provided
grants to Obama’s DCP in the late 80s and Rolling was a part of the school reform effort in which
both Bill Ayers and Obama participated. Obama joined the board of the Woods Fund in 1993 in
1999 he would be joined on the board by Bill Ayers.’ (Steve Diamond, ‘Who “sent” Obama?’
globallabor.blogspot.com, April 22, 2008)^53
Obama’s role in heading up the Chicago Annenberg Challenge meant money, prestige, and
above all an excellent chance to network with the lakefront oligarchs: ‘... the Annenberg Challenge
money came through anyway due to the efforts of Bill Ayers, among others. It had to be matched 2
to 1 by corporate and foundation money (in fact, they raised an additional $60 million by 1999), so
the Board Chairmanship would have allowed Obama to be in touch with the powerful money
interests in Chicago, including possibly the Pritzker Family and others that Kaufman mentions in
his story. Penny Pritzker would join the board of the Chicago Public Education Fund which
received its startup funding from the Annenberg Challenge as the Challenge wound down in 2001 -
the Challenge, in effect, handed the baton of support for school reform to the CPEF. Penny Pritzker
[who owns a share of the Hyatt Hotel fortune, built on the backs of super-exploited Hispanic
cleaning ladies] is now a key Obama campaign insider in charge of fund raising.’ (Steve Diamond,
‘Who “sent” Obama?’ globallabor.blogspot.com, April 22, 2008)
Today, Ayers presents himself not as terrorist vermin, cowardly butcher and mass murderer, but
rather as a theoretician of educating children, and Midwest moralist to boot. Ayers wrote on his
website in a January 19, 2008 essay on school reform: “The dominant narrative in contemporary
school reform is once again focused on exclusion and disadvantage, race and class, black and white.
‘Across the US,’ the National Governor’s Association declared in 2005, ‘a gap in academic
achievement persists between minority and disadvantaged students and their white counterparts.’
This is the commonly referenced and popularly understood ‘racial achievement gap,’ and it drives
education policy at every level. Interestingly, whether heartfelt or self-satisfied, the narrative never
mentions the monster in the room: white supremacy....Gloria Ladson-Billings upends all of this
with an elegant reversal: there is no achievement gap, she argues, but actually a glancing reflection
of something deeper and more profound—America has a profound education debt. The educational
inequities that began with the annihilation of native peoples and the enslavement of Africans, the
conquest of the continent and the importation of both free labor and serfs, transformed into