Loretta Augustine and Yvonne Lloyd encouraged Barack to focus on the sprawling Altgeld Gardens public housing project, just east of where they lived. They introduced him to their pastor at Our Lady of the Gardens, Father Dominic Carmon, and Obama also met with parents whose children attended Our Lady’s small Catholic grade school. He was introduced to Dr. Alma Jones, the feisty principal of Carver Primary School and its adjoining Wheatley Child-Parent Center, virtually all of whose students came from within Altgeld. Jones was immediately impressed with Barack. “Talking to him, he was so much older than he was. It was like talking to your peers rather than somebody the age of your children.” In a community where few people could imagine meaningful change, Jones stood out as an important voice of encouragement for a young organizer venturing into unfamiliar territory.
Despite Altgeld residents’ letters to Mayor Washington complaining about “heavy drug traffic” seven days a week, no city residents were more completely ignored and forgotten than the tenants of Altgeld Gardens. Dr. Gloria Jackson Bacon, who almost single-handedly provided medical care to Altgeld residents for decades, explained that by the 1980s “many of them did not venture outside. Many of them lived almost like insular lives inside of Altgeld.” Bacon recalled others speaking pejoratively of “ ‘those people out there, those people out there,’ and I’d say, ‘These are your people.’ ” Loretta Augustine remembered once taking some Altgeld schoolchildren to the zoo and realizing that “one or two of the kids had never been downtown before.” Loretta referred to Lake Michigan, and “the kid responded, ‘Chicago has a lake?’ ” As Alma Jones told one reporter who visited her school, “Altgeld Gardens is an isolated, enclosed island. We have no stores, no jobs and one traffic signal.”14
Barack continued his weekly get-togethers with Asif Agha, but his social life was so meager that Kellman and Mary Bernstein discussed ways to help him meet more people his own age. “He felt to me like a nephew,” Mary remembered, with Barack calling her “Sistah,” and she calling him simply “Obama.” In her eyes, Barack “was always serious,” indeed “driven,” but above all “he was very solitary.” Bernstein recalled that Barack once asked her, “How am I going to get a date?” working in Roseland and spending his evenings at meetings or visiting DCP parishioners. “You don’t want to date any of the women I know,” Mary humorously replied. “They’re all old, and they’re all nuns.”
Loretta Augustine, Yvonne Lloyd, and Nadyne Griffin were all looking out for the young man’s welfare. “I felt very protective, very motherly towards him,” Loretta later told journalist Sasha Abramsky. “We were worried that he wasn’t eating enough,” Yvonne Lloyd recalled. “We were always trying to make him eat more.” Loretta could see that Barack was “very focused” and “very serious,” and more than once she suggested he lighten up. “You shouldn’t be so somber and uptight and serious all the time.” Obama later said he was indeed “very serious about the work that I was trying to do.” Marlene Dillard’s strong interest in jobs had her spending as much time with Barack as anyone, and though she found him “very dynamic” and “very sincere,” his maturity meant she “never looked at him as a son.” But Nadyne Griffin felt just like Loretta did: “He was just like a son to me,” and Tom Kaminski found the church ladies’ solicitude heartwarming: “Everyone wanted to be his mother, everyone thought she was his mother,” and “I felt like an uncle.”
Barack stayed in touch through regular long-distance phone calls with old friends like Hasan Chandoo, Wahid Hamid, and Andy Roth, and in late February, he sent Andy a long letter that was similar to the one he had written Phil Boerner three months earlier:
As I may have told you on the phone, when you’re alone in a new city, the fullness or emptiness of the mailbox can set the tone for the entire day.
Work continues to kick my ass. A lot of responsibility has been dumped on me: I’m to organize an area of about 70,000–100,000 folks and bring the local churches and unions into the action. I confront the standard stuff: the turpitude of established leaders (i.e. aldermen, preachers); the lassitude of the masses; the “we’ve seen middle class folks come in here before and make promises and ain’t nothin’ happened” attitude, which is true; my own inhibitions about playing for power and manipulating folks, even when it’s for what I perceive to be their own good. At least once a day I think about what I’m doing out here, and think about the pleasures of the upwardly mobile (though still liberal Democratic) lifestyle, and consider chucking all this. Fortunately, one of two things invariably snap me out of my brooding: 1) I see such squalor or degradation or corruption going on that I get damned angry and pour the energy into work; or 2) I see a sign of progress—one of my leaders, a shy housewife, dressing down some evasive bureaucrat, or a young man who’s unemployed volunteering to help distribute some flyers—and the small spark will keep me rolling for a whole day or two.
Who would have ever believed that I’d be the sucker who’d believed all that crap we talked about in the Oxy cooler and keep on believing despite all the evidence to the contrary. Speaking of contrary, I’m in such a state for lack of female companionship, but that will require a whole separate exegesis.
A few weeks later, Barack sent a postcard to his brother Roy and his wife Mary, and a longer message to Phil Boerner. He thanked Phil for his encouraging comments about the short story Barack had sent him, but he emphasized what a “discouraging time” he was having:
Unfortunately, I haven’t had much time for writing (stories or letters) lately, what with this work continuing to kick my ass. Experienced some serious discouragement these past three weeks, mainly because of the incredible amount of time to get even the smallest concrete gain. Still, I’m putting my head down and plan to work through my frustrations for at least another year. By that time I should have a fairly good perspective on both the possibilities and limitations of the work.15
No one in mid-1980s Chicagoland had anywhere near the degree of success Jerry Kellman did in winning major grants from the Campaign for Human Development, the Woods Fund, the Joyce Foundation, and Tom Joyce’s small but always-pioneering Claretian Social Development Fund. Grant makers regularly visited the organizations they supported, and by early 1986, Jerry had been introducing Barack as a new mainstay in DCP’s Far South Side organizing work. Archdiocesan CHD staffers Ken Brucks and Mary Yu met Barack through Kellman, but the two most influential funders Barack got to know that winter were Woods Fund director Jean Rudd and program officer Ken Rolling. Jean had become Woods’s first staffer five years earlier. Ken, like Greg Galluzzo, was a former Catholic priest who had spent more than half a dozen years in organizing before joining Jean at Woods in 1985. Woods’s commitment to organizing was reaching full flower just as Jerry and then Barack arrived on the scene. As Jean deeply believed, “community organizing is intended to be transformational for ‘ordinary’ people. Through its training and actions, people recognize their worthiness, their legitimacy, their place in a democracy, their power, their voice.” That was the work, and the teaching, that she and Ken wanted to support and champion.
Decades later Jean remembered when Jerry first brought Barack to meet them. “In that first meeting, I was very, very impressed…. He was very, very reflective, very candid … very winningly … humble about what he had to catch up on” about organizing and about Chicago. “I believe I said to my husband, ‘I’ve really met the most amazing person today.’ ” But most of Woods’s actual contact with DCP, CCRC, and other grantees like Madeline Talbott’s ACORN was handled by Ken Rolling, who was even more impressed upon first meeting Barack. “I’ve just met the first African American president,” he told his wife Rochelle Davis that evening. Ken said much the same thing to CHD staffer Sharon Jacobson, who a quarter century later remembered it just as Ken and Rochelle had: “I want you to watch this guy, Sharon. He’s going to be president of the United States one day.”
Jacobson played a leading role in CHD’s grant making in Chicago, and Renee Brereton, based in Washington, was the crucial staffer for