Nobody knows the answers to your questions but thank you for axing.
http://www.claremont.org/publications/crb/id.1852/article_detail.asp
“....Nevertheless, because fully to know where anyone is going requires grasping whence he comes, let us open ourselves to wonder how, minus miracles, a 10-year-old boy without obvious talent who had lived in Indonesia since age six ends up with an eight-year scholarship to Hawaii’s most exclusive school; a scholarship to Occidental College; a transfer into Columbia University; acceptance into Harvard Law School, and editorship of its law review; and how he goes from job to prestigious job without apparently mastering any of the previous ones. No wonder some of Barack Obama’s supporters treat him as if he were anointed by an extraterrestrial power. “
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His mother’s parents, who raised him, seem to have been cogs in the U.S. government’s well-heeled, well-connected machine for influencing the world, whether openly (”gray influence”) or covertly (”black operations”). His mother spent her life and marriages, and birthed her children, working in that machine. For paradigms of young Barack’s demeanor, proclivities, opinions, language, and attitudes one need look no further than the persons who ran the institutions that his mother and grandparents served—e.g., the Ford Foundation, the United States Information Agency, and the Central Intelligence Agency—as well as his chosen mentors and colleagues.
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In sum, though the only evidence available is circumstantial, Barack Obama, Jr.’s mother, father, stepfather, grandmother, and grandfather seem to have been well connected, body and soul, with the U.S. government’s then extensive and well-financed trans-public-private influence operations.