The CIA chiefly recruited two kinds of people. First, the good blood, good bone, old-line WASP Skull and Bones types on the grounds that they were less likely to betray America because they pretty much owned it. For example, there is more than a little circumstantial evidence that George H.W. Bush, who, when he was appointed CIA Director in the mid-1970s was described as being an "outsider," had previously helped the CIA with the Bay of Pigs and other anti-Castro operations in the 1960s, using his offshore oil drilling rigs in Mexican waters not terribly far from Cuba. There's nothing too shocking about this idea. In fact, GHW Bush may even have sacrificed a good deal of wealth to stay in an offshore business helpful to the CIA. He split with his partners, who kept the domestic onshore oil business, which they turned into the huge firm Pennzoil.
Obama is not a particularly cosmopolitan person, at least not compared to his parents. But the three foreign countries where he has had the strongest ties -- Indonesia, Kenya, and Pakistan -- were particularly of interest to the CIA.
Barack Obama Sr. was a protege of Tom Mboya, the Kenyan Luo politician who was famously Washington's man in a three way struggle for power within Kenya between the pro-Soviet Luo Oginga Odinga and the pro-British Kikuyu Jomo Kenyatta. Obama Sr. claimed to have been the chief witness to the 1969 assassination of Mboya, a landmark event in Kenyan history equivalent to the JFK assassination in the U.S. Obama Jr. left this out of his autobiography, but that Obama Sr. claimed this are now well-documented.
Obama's mother worked in the late 1960s at the U.S. Embassy in Jakarta, Indonesia, which was Ground Zero for the CIA after the 1965 Communist putsch and subsequent military massacre of leftists. Indeed, Dreams from My Father refers to her conversations on the job with CIA men. David Remnick's biography of Obama, The Bridge, explains that his mother went on to a career in microlending social reform in Indonesia and Pakistan funded by the Ford Foundation, the World Bank, and a Saudi bank.
At Occidental, Obama's best friends were rich Pakistanis leftists. In 1981, he visited Pakistan and stayed at a friend's estate, whose politician father became the caretaker Prime Minister of Pakistan in 2008. Pakistan in 1981, of course, was crucial to the CIA's attempts to rally an armed resistance to the Soviets over the Khyber Pass in Afghanistan. These are the kind of social connections that would be of interest to the CIA.
After he got out of Columbia, Obama got a job at an international business newsletter firm, Business International, where, he says, he felt like "a spy behind enemy lines." That reflects his leftist ideology, but I suspect he's amusing himself as well by referring to the fact that Business International had served to provide cover to at least four CIA agents over the years.
How did Obama wind up working at a CIA front? Coincidence? Perhaps, but maybe he had some advice. Maybe somebody made a phone call for him.