From the New Republic:
Indeed, during his three years in South Chicago, Obama was constantly having to scale back his objectives as one project after another faltered. First, he got community members to demand a job center that would provide job referrals, but there were few jobs to distribute. Then, he tried to create what he called a "second-level consumer economy" in Roseland consisting of shops, restaurants, and theaters. This, too, went nowhere. At that point, Kellman advised Obama to move elsewhere. "Stay here, and you are bound to fail," he told him.
By late 1987, he seems to have grown disillusioned with the underlying principles of community organizing.
..if you examine carefully how Obama conducted himself as an organizer and how he has conducted himself as a politician, if you consider what he said about organizing to his fellow organizers, and if you look at the reasons he gave friends and colleagues for abandoning organizing, then a very different picture emerges: that of a disillusioned activist who fashioned his political identity not as an extension of community organizing but as a wholesale rejection of it.
Obama helped the residents wage a successful campaign to get the Chicago Housing Authority to promise to remove asbestos from the units; but, after an initial burst of activity, the city failed to keep its promise. (As of last year, some residences still had not been cleared of asbestos.) In waging these campaigns, Obama's organization added staff, gained adherents, and won church support, including from the congregation of Reverend Jeremiah Wright. But it failed to stem the area's overall decline. "Ain't nothing gonna change, Mr. Obama," says one resident quoted in Dreams from My Father who grows disillusioned with the Developing Communities Project. "We just gonna concentrate on saving our money so we can move outta here as fast as we can.
Sometime before he left Chicago, he wrote an article for a magazine called Illinois Issues that would eventually appear in an anthology titled After Alinsky: Community Organizing in Illinois. In the article, he insisted that his project had achieved "impressive results" in South Chicago. While acknowledging that the "exodus from the inner city of financial resources, institutions, role models and jobs" posed difficulties for organizers, he insisted that "none of these problems is insurmountable."