Meet Valerie Jarrett, Barack Obama's fixer.

The black Tahoe slows to a crawl as Valerie Jarrett, Barack Obama's political wise woman and longtime friend, gestures toward a forlorn expanse of weeds running along State Street in the blighted Bronzeville neighborhood on Chicago's South Side. "It was just this wall of high-rise buildings along the expressway," she says, "And now--it's all gone."

Jarrett is referring to the Robert Taylor Homes, the two-mile stretch of tenements named for her grandfather that once loomed over this spot. A housing activist and the first African American to head the Chicago Housing Authority (CHA), Robert Taylor famously resigned in 1950, when the city council rejected a development plan that would have spurred integration. In 1962, three years after Taylor's death, the Robert Taylor Homes were opened and loudly touted as the largest affordable-housing development in the nation. But, by the time the CHA removed the last occupants in 2006, the drug-and-blood-soaked towers had, ironically, become a super-sized symbol of the racial and economic segregation Taylor had long fought. Back in the day, a vehicle like Jarrett's cruising at this speed along this block would have drawn hostile looks—and maybe more—from the gangs who fought for control of the development.

But Jarrett—a pretty, petite woman looking decidedly not-of-the-neighborhood with her Chanel sunglasses, trim black suit, and crisp white blouse—has brought me to this spot not because of its past but because she sees Chicago's future here. A former city planning commissioner turned for-profit developer, Jarrett has been at the forefront of an effort to redevelop this failed space for going on a decade. She says she didn't get into urban renewal specifically to redeem her grandfather's legacy. But, having been "sensitized" to his perspective, she has long grappled with "figuring out a way to improve the health of the city by giving people who had been living in isolation better opportunities to move toward self-sufficiency." (Yes, she really talks like that.) Soon, Jarrett enthuses, a cluster of town homes will rise on this site, some set aside for public housing, others priced for the working poor, and still others sold at market rate. With smart planning, and a little luck, the development will help revitalize the surrounding area--as has occurred in other neighborhoods.

Indeed, State Street is just one stop on our more than two-hour tour. Jarrett glows as we wind through neighborhoods where public housing units have been strategically scattered among privately owned homes. "One house on that block was public housing. I won't tell you which one," she challenges as we ease down a tidy residential lane once dominated by boarded-up vacants. Now and again, she gets so wrapped up in showing off her handiwork that she forgets basic road rules—like staying in her lane or not stopping in the middle of an intersection when the light is green. (Note to self: Next time, offer to drive. ) Jarrett seems not to notice the angry honking.

When I set out to discover what makes the woman described as Obama's "big sister" tick, it never occurred to me I'd wind up spending a Thursday afternoon cruising Chicago's poorest neighborhoods. After all, Jarrett's c.v. reads less like that of a bleeding-heart liberal than a sedulous careerist: Post-law school, she spent six years as a real estate attorney followed by eight years at City Hall (first in the legal office, then as deputy chief of staff to the mayor, and finally as commissioner of planning and development). She then decamped for the Habitat Co. (of which she is now CEO), one of Chicago's largest for-profit real estate development and management firms and, since 1987, the court-appointed overseer for all of Chicago's new non-elderly public housing. She is the vice chair of the University of Chicago board of trustees, the chair of the university's Medical Center board, and trustee of another dozen corporate, civic, and charitable organizations, including the committee spearheading Chicago's bid for the 2016 Olympics. And of course, these days, she is frequently on the plane and perpetually on the phone with her good friend Barack. In a dissection of The Chicago Establishment, the 51-year-old Jarrett would be found deep in the heart.

But pursuing change from within has long been Jarrett's m.o. Like Obama, she does not seek to fight the system so much as infiltrate it, scale it, and make it work for her. It is a quieter, less dramatic form of activism that can cause friction with some of Jarrett's more traditional liberal allies—much the way Obama's post-racial positioning has raised eyebrows among older-generation black leaders such as Al Sharpton and, more caustically, Jesse "I want to cut his nuts off" Jackson. For Jarrett, however, unifying people behind the system rather than against it has become something of an art form. Increasingly, her goal is to help Barack Obama do the same.

Behind the aggressively bland title of "senior adviser," Jarrett's cardinal role on the Obama campaign is to serve as an extension of the candidate. She is Obama's eyes and ears at meetings and events. When she speaks, it is in his voice. She is often the one to deliver harsh truths to Obama--and to others on his behalf. And, when there is courting of vital constituencies to be done, Jarrett is an undisputed master. (Late last month, for instance, she headed to New York for a heart-to-heart with Democratic money maven and hard-core Hillaryite Maureen White—with whom Jarrett was looking forward to spending more time on Martha's Vineyard this month.) Among the most ticklish situations that she's been called upon to address thus far is Obama's standing with black voters.

Nowadays, anyone questioning Obama's popularity among African American voters would be laughed from the room. Up through last year, however, the landscape was grimmer. Polls showed the Illinois senator trailing Hillary Clinton among this key Democratic demographic, a situation complicated by the loyalty many black political leaders felt toward Bill Clinton. With the campaign focused heavily on Iowa, limited resources had been devoted to courting the black community. Worse still, there persisted grumbling around the edges of the race about whether the half-white, Ivy-League-educated, yuppie-ish Obama was "black enough." Obama was in a tricky spot. Rejecting the mantle of Black Candidate, he had to keep his distance from some of the traditional "black issues" (not to mention some of the traditional black leaders) that could racialize the election. Even assuming his poll numbers eventually ticked up, if black leaders felt they and their issues were being dismissed, there would be hell to pay.

Jarrett had a fine line to walk: reassuring without overpromising, energizing without polarizing. And she lacked the national profile or civil rights credentials that might have made the job easier. If anything, her background carries the scent of privilege and cosmopolitanism that one might expect to cause trouble in certain circles.

Robert Taylor, Jarrett's maternal grandfather, is not her only illustrious forebear. Higher up the family tree, Taylor's father, Robert Robinson Taylor (the first black student to graduate from MIT), was an architect, instructor, and vice-principal at the Tuskegee Institute at the turn of last century. And his father, Henry Taylor, the son of a white slave-owner and a black mother, managed to build a successful contracting and construction business in pre-Civil War North Carolina.

Valerie Bowman's own upbringing was a blend of the exotic and traditional. At the time of her birth, her parents were living in Shiraz, Iran, where father James, a geneticist and pathologist, was helping set up a hospital. When Valerie was five, James moved the family to London for a one-year fellowship. In 1963, the Bowmans returned to Chicago, where James joined the University of Chicago faculty. Settling into the eclectic Hyde Park neighborhood, Valerie grew up surrounded by family. Recalling the aunts, uncles, grandma, and 17 cousins who lived within a few blocks of the house, Barbara Bowman chuckles about raising her daughter in "a family compound."

Today, Jarrett lives in a stately art-deco co-op in the Kenwood neighborhood just north of Hyde Park with her daughter Laura. (Home for the summer from Harvard Law, Laura is the only child of Jarrett's short-lived union with Dr. William Robert Jarrett, son of the late Sun-Times columnist Vernon Jarrett. The couple wed in 1983 and divorced in 1988; five years later, William suffered a fatal heart attack.) Deeply rooted in what is commonly referred to as Hyde Park-Kenwood, Jarrett threatens to tear up as we tour some of its more sentimental landmarks: her parents' home (on the same elegant, leafy street where the Obamas now live), the University of Chicago (where her father remains a professor emeritus in the Division of Biological Sciences), the university-affiliated Lab School that both she and her daughter attended (all pale limestone and ivied), the site of her first date (a grassy expanse of park perfect for a moonlit stroll), the house that her maternal grandmother moved into the minute the segregationist housing covenants were struck down in the 1950s.

As grounded as Valerie is in Hyde Park, the Bowmans saw to it early that their only child's perspective extended far beyond it: Well into her teens, Valerie spent summers traveling the globe (Ghana, Nigeria, Egypt ...) with her parents, as James conducted research and Barbara, a co-founder of the Erikson Institute for child development, studied other cultures' education models. For her last two years of high school, Valerie went east to the Massachusetts prep school her mother had attended. She headed west to Stanford for college and then on to the University of Michigan Law School. With J.D. in hand, she promptly returned home to Chicago. But, unlike Obama who cut his political teeth as a community organizer, Jarrett followed a more inside route, winding through both the private sector and City Hall.

Jarrett's comfort with the establishment and membership in the black elite helped shape the strategy she formulated last summer to introduce Obama to black voters. Jarrett put together an African American working group and tasked it with targeting black leaders. But, according to participant Eric Holder, Jarrett urged the team to think beyond black churches and high-profile spokesmen and connect with black media outlets, businesspeople, and other opinion leaders "who really do influence people but who aren't necessarily as well-known as others." And, while early voting states and big urban centers were an obvious focus, says Holder, she also pushed outreach to mid-level cities with smaller black populations like Albany "to generate support in places where you would not expect it." If it wasn't exactly an end-run around traditional black leaders, it was clearly a recognition that the community's power-base has expanded.

Even with the new breed of powerbrokers on board, Jarrett still needed to reassure traditional leaders that Obama shared their basic ideals despite his "post-racial" approach. Arguably, there was no better preparation for this task than the eight-year political education Jarrett received inside Chicago's fractious City Hall.

In 1987, Jarrett joined the city's Corporation Counsel office in the wake of the reelection of Mayor Harold Washington. Like many of the young, liberal idealists who followed Washington into City Hall, Jarrett hailed from Chicago's Independent strand of Democrats (for which Hyde Park is ground zero), who for years had been shut out of government by Mayor Richard J. Daley's machine. But, in 1989, Daley the Younger reclaimed his father's perch and the Independents began to flee. Jarrett opted to stay on, much to the dismay of her Independent allies, who warned that she would get sucked into the machine and lose her progressive ideals. (It didn't help that the '80s were a particularly nasty period of racialization in Chicago politics.) Jarrett says she shared some of those same concerns but wanted to see if she could continue her development plans under the new regime. Besides, she chuckles, "having grown up here, how much heat am I going to take? People knew who I was. They knew my family."

Before long, she had established herself as one of Daley's most trusted advisers. And so, for the next few years, as Jarrett moved from post to post within the administration, she found herself negotiating the bitter divide not only between competing interest groups (developers, community activists, politicos ...) but also between Daley's people and their Independent antagonists, such as Hyde Park Alderman Toni Preckwinkle. Daley and Preckwinkle squabble about pretty much everything—"it doesn't have to be a policy difference," sighs Jarrett. "Whatever the issue would be, sometimes I would go to her and say, 'Here's the mayor's perspective.' And I would go to the mayor and say, 'Here's Toni's perspective.'" But mostly, laughs Jarrett, "what I tried to do was get them to agree on issues for which I was responsible" like development.

Jarrett found herself calling on these same mediation skills to personally bridge the gap between Obama and the more conventional black leadership, including civil rights icons and old-school purveyors of identity politics. She quickly became the campaign's chief ambassador to this cohort, meeting with leaders and fielding their calls to explain Obama's vision, answer questions, and address concerns.

One of Jarrett's better-known conferees has been the Reverend Al Sharpton. As Sharpton tells it, he was initially skeptical of Obama—until Jarrett went to work on him. "Part of what moved me from, 'Who is Barack Obama and what is he really about?' to 'Yes, this is a guy who can help make changes even if we're not on the same page in terms of style and approach'--a lot of that came from talking to her," he gushes. Jarrett was upfront about areas where Obama disagreed with Sharpton, and she took care not to raise unrealistic expectations. ("She was very clear that the senator was not trying to be 'a black leader,'" says Sharpton.) But, he adds, her "sincerity and soft touch" soothe the waters even when she's saying "no." "Sometimes I've called into the campaign with an issue I thought was upsetting," recalls Sharpton. Whether the matter is political (such as the campaign's response to a smear) or policy related (such as Obama's vote on the FISA bill), says Sharpton, "she's so calm herself that you find yourself fighting to stay calm as well, trying to even out your tone."

And watching her work her mojo on Clinton loyalists within the black leadership left him "in awe," asserts the reverend. "There were a lot of passions, a lot of debts owed the Clintons, and for her to navigate those [relationships] without making people feel less than respected but at the same time not make it look like the senator had to move their agenda forward was masterful." Says Sharpton, "At the end of the day, she gained everyone's respect—something unheard of—and everyone's trust."

Now, Al Sharpton is a smart guy: He knows the wisdom of lauding the woman at the right hand of the man poised to be president. But the reverend's description of Jarrett in action is echoed by numerous people she has worked with (and even clashed with) over the years. Plus, Jarrett's sprawling network of friends and colleagues has the markings of someone who leaves her bridges intact. "She may be one of the most plugged-in people in the United States," jokes Obama press maven Anita Dunn. Certainly few people in Chicago are better connected. (Jarrett boasts an impressive entry on Muckety.com's list of the city's "100 best networked.") She knows the aldermen, the ward-heelers, the business execs, the union bosses, the neighborhood activists, the religious and civic leaders, the journalists, the political appointees and consultants, and the bureaucrats. When someone needs help organizing a benefit for their civic group, finding an internship for their kid, or raising money for their political campaign, Jarrett is a good woman to call. (If the constantly vibrating cell phone and ever-present Blackberry are any indication, plenty of people do just that.) In turn, when Jarrett needs buy-in for a project—be it revamping a rundown neighborhood or helping a friend run for president—she is well positioned to stroke or twist the appropriate arms.

With Jarrett's national profile ascendant, few of her fellow insiders are eager to criticize. Jarrett is described by past and current colleagues as "firm," "direct," "demanding," and quick to question a position or action she disagrees with. (And, when she asks, you better have answers, says Obama strategy guru David Axelrod: "She can send some pretty bracing e-mails.") Even Preckwinkle, who recently endured a couple of run-ins with Jarrett--one over Preckwinkle's vote on an Olympic-related issue and another over some Obama criticisms she made to The New Yorker—declined to discuss their periodic clashes. The audibly tense alderman emphasized that despite an "occasionally strained" relationship, "we've continued to be friends over time."

Jarrett's success as a mover and shaker is testament to her conviction that one can pursue outsider ideals from an insider vantage point. Fittingly, it was in the service of proselytizing this belief that she first encountered Barack Obama. By now, the story of Obama and Jarrett's initial meeting is familiar: In 1991, a young, civic-minded attorney named Michelle Robinson was thinking about joining Daley's team. Before accepting, Michelle asked if Jarrett, her potential boss, would mind talking through a few things with her future husband. "He was worried about the same things that I worried about when Daley first got elected," says Jarrett. "Would [the mayor] be sufficiently progressive? Would Michelle get caught up in the Democratic machine? Would she be able to—if she disagreed with something the mayor wanted to do, would she be forced to do it?"

Jarrett assures me the "interview" wasn't as odd as it sounds: "As far as I was concerned, the situation had shifted from me being the person interviewing Michelle to selling her on the job. And, if that meant I had to sell her fiancé too—because this is what I do—I was happy to have dinner with them." Jarrett ended up talking about herself—her family, her passions, her politics, her own experiences dealing with City Hall—until she had adequately eased the couple's concerns (many of which she had previously wrestled with herself).

And, so, the Obamas were drawn into Jarrett's inner circle. She and Michelle in particular clicked. ("Ohhhhh yeah," says one insider. "They look out for each other.") When Jarrett left the mayor's office for the planning commission, she took her protégé with her. Later, Michelle served as an employee-officer of first the University of Chicago and later the medical center during Jarrett's tenure on both boards. Similarly, as Barack's political ambitions began to gel, Jarrett was on hand with thoughtful counsel—as well as insider knowledge of the Chicago political scene and its key players. Four years later, though the stakes are higher and the stage bigger, Jarrett provides some of the same aid.

It's impossible to judge the precise impact of Jarrett's courting of black voters, or even black leaders. (So many variables at play: Obama's win in lily-white Iowa, Bill Clinton's meltdown in South Carolina, Jesse Jackson Sr. versus Jesse Jackson Jr., Jeremiah Wright...) But Jarrett's colleagues laud her for aggressively tackling the issue and clearing away as many potential hurdles as possible along Obama's path to 90 percent support among African Americans. Better still, she did it in that low-key, work-the-system style that she has long favored—and that Obama is claiming as a hallmark of his leadership. Of course, as is so often the case, playing a quiet, inside game lacks the purity—and clarity—of struggling against the system. And it can be tough at times to tell just how much you are really accomplishing.

Our last tour stop was, for years, the nation's most notorious housing project: Cabrini-Green, located on the Near North Side next to some of Chicago's toniest neighborhoods. Though much of the complex has been razed, three of the towers still stand, all the more prominent because of the open space around them. Many units in the shabby, white buildings are vacant, and some bear the scars of fires. Jarrett calls these "the hostage buildings," units unable to come down because of legal wrangling with residents upset over the redevelopment process. They are a concrete reminder of how far the CHA's "Plan for Transformation" has yet to go.

Being part of the establishment invariably invites suspicion from those on the outside, and, with a project as overwhelming as overhauling Chicago's public housing, the opportunity for conflict and controversy is limitless. Some resident groups and homeless advocates contend that the city and its for-profit development partners (like Habitat) are gaming the system, letting properties deteriorate so they can be condemned and then more easily redeveloped. "If what they wanted to happen was that poor people in the city go away, it was a good plan for the city. But as far as people needing housing is concerned, it wasn't a good plan," charges Carol Steele, co-founder of the Coalition to Protect Public Housing. Periodically, the local press runs stories detailing the overhaul's failures: the missed construction deadlines, the culture clashes in the mixed-income developments, the lack of meaningful integration (politics being what they are, most public housing still winds up in non-affluent, non-white neighborhoods), maintenance and construction problems with some newer complexes, and, most tragically, the struggle of many poor families to find stable replacement housing--in some cases, years after being turned out of the high-rises. With her Obama ties, Jarrett has also begun drawing national scrutiny. In late June, for instance, The Boston Globe ran a scathing account of how ongoing problems at the Habitat-managed Grove Parc Plaza prompted the city to seize the complex in 2006 and reassign oversight to a Boston-based firm.

Jarrett acknowledges that Habitat has occasionally taken on more than it could handle. More broadly, she admits that progress on the "Plan for Transformation" has been much slower than anyone expected—and that the housing crash stands to exacerbate the problem. But, even at Cabrini-Green, the snags of capitalism and politics notwithstanding, she sees progress. The site is ringed by newer residential developments, including market-rate town homes valued at over half a million dollars. For Jarrett, having people pay that kind of money to live in the shadow of a place once known as "Little Hell"—alongside some of Cabrini's relocated residents—is unbelievable. "So this is the perfect view!" she announces, circling around to the north side of the towers. "Market rate, single-family homes across the street, juxtaposed with Cabrini-Green."

Well, not exactly perfect. Chicago is nowhere near achieving Robert Taylor's dream of safe, affordable housing for all. But it's a start--and Jarrett has always been more inclined toward evolution than revolution. "In the end," she tells me, "I think some things take time because they should."

Michelle Cottle is a senior editor at The New Republic.

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