On a mild September day in 1999, Gary Comer drove from his Gold Coast apartment to a neighborhood on Chicago’s Far South Side. Known as Pocket Town, it’s a small triangular “pocket” of Greater Grand Crossing bordered by Oakwood Cemetery to the north, the Norfolk Southern tracks to the west, and the Metra tracks to the east.

Like many parts of the South Side, Pocket Town had become overrun with drug dealers and gang violence in the 1970s. Block after block was blighted. The local school was failing. Fifteen percent of residents lived below the poverty line, and unemployment topped 25 percent.

Comer, a diminutive 70-year-old in khakis and a crewneck sweater, got out of his car and walked into the two-story red brick Paul Revere Elementary School. “This little guy, who barely reached my shoulder, came up to me and tapped me,” recalls Shelby Taylor, the principal at the time, a tall man with a deep voice. “He asked to take a tour of the school.”

Days later, Comer wrote a check for $68,000 to fix an electrical problem in the aging building that prevented computers from being used in the computer lab. A grateful Taylor asked Comer what he could do for him in return. Comer responded, “Well, Shelby, I would like a good soul food lunch.” Over greens, grits, and cornbread, Comer told him: “I will use all of my resources to help turn Revere around.”

Dumbstruck, Taylor learned that the unassuming senior citizen was the billionaire founder of the mail-order clothing empire Lands’ End. Comer had graduated from Revere more than half a century before. And it turned out that helping the school was only the beginning. Comer soon resolved to do no less than transform the lives of the families and young people of Pocket Town.

Comer’s hugely ambitious quest contains elements of both the Kalamazoo Promise (a Michigan philanthropist’s pledge to pay for college for all local kids who graduate from public high school) and the Harlem Children’s Zone (an urban renewal program that provides an assortment of “cradle-to-career” services for children and families in New York City’s Harlem neighborhood). The plan he eventually hit upon was to address the interconnected problems facing Pocket Town’s residents: poorly performing schools as well as issues like substandard housing and inadequate health care.

Given his age, Comer knew he’d be unlikely to live to see Pocket Town completely resuscitated. (Indeed, he died of prostate cancer in 2006.) Through the Comer Science and Education Foundation, which he set up in 1998, now run by his son, Guy, 42, he made sure the money would keep flowing. “Gary told me that even though he’d be gone, he would take care of this neighborhood,” Taylor says.

So far, some $86 million of Comer’s money has been plowed into Pocket Town. “[That’s] a fair amount of money for a small neighborhood,” says Robert Sampson, a Harvard sociologist and one of the country’s foremost experts on neighborhood revitalization. It works out to about $43,000 for each of the area’s 2,000 or so men, women, and children.

The big question: What results has that huge investment yielded? And what lessons are there for policymakers, philanthropists, and everyone who cares about the fate of struggling urban neighborhoods?

When Gary Comer was a boy, Pocket Town was an enclave of tidy single-family homes owned by hard-working European immigrants. Many of them had jobs at the nearby rail lines, as did Comer’s father, a conductor; his mother was a homemaker. Comer “was always humbled and amazed at his own success, and he attributed a lot of it to his upbringing,” says his son.

After graduating from Hyde Park High School in 1946, Comer skipped college (too expensive) for a copywriting job at the advertising agency Young & Rubicam in Chicago. He married Francie Ceraulo, who worked in public relations and they had two children, Stephanie and Guy. (Stephanie, now 46, runs a second Comer family foundation.) Meanwhile, in 1963, he turned a passion for sailing and a $30,000 loan into Lands’ End, one of the first catalog companies that sold clothing with a nautical theme.

As he built the business, says Guy, “my dad would often take us back to his old neighborhood.” He would point out his old haunts: his childhood home at 69th and Kimbark, Revere
Elementary, and Oakwood Cemetery, upon whose walls he had played games.

When Lands’ End went public in 1986 (Sears bought it 16 years later), Comer became one of the wealthiest businessmen in Chicago. He began using his good fortune to do “useful things”—including sponsoring Field Museum explorations to South America and funding cancer research.

It was that 1999 visit to Pocket Town that “really got him thinking about helping kids,” says Bill Schleicher, a longtime Comer adviser who manages the family’s assets. Though he did not start out with some grand visionary plan, “he got more and more involved as he . . . learned how impoverished his old neighborhood had become.”

Improving educational opportunities—starting with Revere—was Comer’s top priority. “He believed that was the only way to ensure change in the neighborhood,” says Guy.

Early on, Comer and his staff at the foundation debated whether to prop up Revere or design a new charter school from scratch. They chose the former. “We would’ve had to close down the school for a year in order to turn it into a charter, and that’s where the conversation always stopped,” explains Schleicher. “What would those kids have done [in the meantime]?”

A research junkie, Comer spent countless hours studying Revere. He learned that its students’ reading, math, and writing scores were chronically so low that Revere had been on Chicago Public Schools’ academic probation list for years. Absenteeism was rampant. Taylor, who had started on the job five months before Comer came knocking, was the school’s fourth principal in 18 months. “Gary knew more about my school than I did,” says Taylor.

For every problem Comer encountered, he would propose a solution. To stop students from wearing gang colors, for example, he “bought every single kid—nearly 700 of them—three tops, two bottoms, and a sweater,” says Taylor.

Comer helped set up a science club and sent daily e-mails to its members. He put maps and globes in every classroom. He bought laptops for students. And when President Clinton launched a federal initiative to bring new technology to poor urban communities, Comer personally handled Revere’s bid for funds. “I spent that Christmas with Gary, in my office, filling out the applications,” says Taylor. (Revere wound up receiving $368,000, which paid for a total of 138 computers in its 23 classrooms.)

Taylor says Comer’s commitment to Revere eventually reached upward of $1 million annually—twice as much as the school was receiving from federal and state aid combined. With that money, the school did everything from remodel its auditorium to bring in experts to train teachers.

When students graduated from Revere, they headed to South Shore High School, a couple of miles away, which had an abysmal graduation rate of 50 percent. Comer wanted Pocket Town’s kids to have a strong high school right in the neighborhood. He decided that building a charter school—publicly funded but privately run—was the way to go.

Gary Comer College Prep opened in 2008 and moved in 2010 to a new building, designed by the renowned Chicago architect John Ronan. The neon-green exterior stands out as a true “beacon of optimism,” wrote Blair Kamin, the Chicago Tribune’s architecture critic.

Comer Prep is part of the Noble Network, the city’s highest-performing group of charter high schools. Comer’s foundation owns the building, and the Chicago Public Schools created an attendance boundary for students who live in the neighborhood, guaranteeing them priority enrollment.

Like all Noble schools, it is extremely strict. (Students get “the Catholic treatment,” says Timothy Knowles, director of the University of Chicago’s Urban Education Institute.) For example, a demerit system penalizes students for a wide range of offenses, from classroom misbehavior to untucked shirts. Incurring four demerits costs kids an afternoon of detention and $5.

College counseling is a huge focus. Last year, every graduating senior who went on to college was given a cell phone on the condition that he or she check in regularly with Comer Prep’s full-time alumni coordinator. (While the foundation does not pay students’ college tuition, it helps them secure financial aid.)

Each year between 1999 and 2001, Comer flew Shelby Taylor to his 500-acre farm in southwestern Wisconsin. Against a backdrop of rolling hills, where coyotes and turkeys roamed, the men would discuss the progress being made in Pocket Town. Partly as a result of those conversations, Comer realized that focusing on education alone wasn’t enough. “If he wanted to help improve the lives of kids, he’d [also] have to focus on . . . after-school time and their home life,” says Hank Webber, a former vice president for community and government affairs at the University of
Chicago, who advised Comer.

In 2002, Comer started hosting monthly Saturday morning breakfasts in Revere’s auditorium to ask Pocket Town families about their needs. Turnout was poor at first. “People didn’t trust Mr. Comer,” explains Sam Binion, a neighborhood fixture whom Comer hired early on to boost community involvement. “They thought he’d be just another white man who’d eventually leave them hanging.”

Residents who did attend lamented Pocket Town’s lack of recreational space for kids. There were so few facilities that the South Shore Drill Team, an after-school program for 300 area school kids, had to practice in the street.

Comer decided to build a recreation center (and to cut a $1.5 million check for the drill team). The 80,000-square-foot Gary Comer Youth Center, a blue-and-red Lego-like building—also a Ronan design—opened in May 2006, just months before Comer’s death. It includes a fully operating kitchen that feeds up to 800 kids a day, a roof garden, a media lab, a gym, a dance studio, and more.

Back at Revere, attendance remained low. One reason, Comer learned, was that many students’ immunizations were not up-to-date. “Fifty to 100 kids couldn’t attend school because [of that],” says Schleicher. So the foundation partnered with the University of Chicago’s mobile clinic to provide free annual shots. Then, in 2009, the foundation partnered with the health care provider Access Health to open a clinic inside the youth center. It offers nutritional counseling, sex education, and psychotherapy to every Pocket Town child as of this year—all for free.

Comer eventually became convinced that a main reason for Revere’s high turnover (a third of its student body changed each year) was that few young parents in Pocket Town owned the homes they lived in. Instead, they rented (often in subsidized housing or from slumlords) or lived with older relatives—an inherently less stable situation. Many homes were in rough shape; nothing had been built there since the 1970s.

To encourage homeownership, in 2005 Comer and his foundation invested $12 million in an affordable-housing program called Revere Way. They hired Lee Reid, a veteran of the Chicago Housing Authority, to develop it.

The initial plan was to tear down the most dilapidated of Pocket Town’s existing housing stock to make room for 90 new two-story red brick homes, built in three phases. “Our goal was to find young families in the community who could [buy] the new homes and help stabilize Pocket Town,” explains Reid.

Comer’s Pocket Town project has already yielded some clear successes. The youth center, for example, offers not only recreational activities for kids who don’t have many but also provides hundreds of year-round jobs for them. The center’s garden yields 6,000 pounds of vegetables annually. Perhaps most important, the center serves as a much-needed haven from the violence that continues to plague the area. In 2012, Greater Grand Crossing saw 36 homicides—and one shooting in Pocket Town itself. “Being here has changed me because I’ve learned how to be safe,” says Demetrius Walker, 15, a youth center regular. “It keeps me out of the streets.”

Comer’s health initiatives have been a slam dunk too. This year, for instance, the clinic has vaccinated 700 youths—a third of whom would not have been able to return to classrooms otherwise.

Unfortunately, when it comes to schools and housing, results have been mixed. Let’s start with Revere Elementary. Students initially showed significant academic improvement. For example, while only 20 percent of them met the national academic standards in 2001, 52 percent did in 2006. As a result, Revere came off academic probation.

But then progress stalled. According to Chicago Public Schools’ 2012 scorecard, less than 25 percent of Revere students meet the national student performance average. Unsurprisingly, Revere is back on probation. “The situation is dire now,” Taylor says sadly.

Schleicher blames CPS red tape: “It cost us more money than we expected, and we did not get the type of results we wanted as soon as we wanted.”

By contrast, Comer Prep is shaping up to be an academic success. Over the past three years, the average ACT score for its students has jumped from 13.7 (out of 36) to 20.1—the third-highest improvement among CPS high schools. And Comer is on track to graduate 85 percent of its students, according to CPS. Last spring, every one of Comer’s 127 seniors went on to college. “I wish [my dad] could have seen the first class graduate,” says Guy. “He would’ve been tremendously inspired.”

But look more closely and the picture gets less rosy. “A lot of my friends who came up from Revere with me have left because they couldn’t handle the rules,” says Mark Franklin, a senior. Noble Network has come under fire from various education activist groups for weeding out low-performing students to improve its schools’ academic standings. Even Noble’s superintendent, Michael Milkie, admits that its 12 schools lose about a third of their students before their senior year.

That’s a troubling development, given that Comer’s mission was for Comer Prep to serve all the teens of Pocket Town. One reason for the high dropout rate, parents say, is simple math: Those $5 disciplinary fees add up fast in a neighborhood where the median household income is just $21,361. (While Comer Prep has not waived the fees, last year the foundation added grades 6 through 8 to the school, figuring that would give students more time to adjust to the demanding atmosphere.)

As for housing, the Revere Way homes have indeed transformed large portions of Pocket Town. Their cookie-cutter structures and well-groomed lawns dot the neighborhood’s grittier cityscape. Binion points to a single block lined with nine of them. “Almost every one of these houses was where drug and gang leaders [once] lived,” he says.

But it turned out that Pocket Town residents weren’t so eager to buy. The first 30 homes went on the market in 2006; by 2007 all had been purchased—but only one by a family that actually lived in Pocket Town. The Revere Way homes were just too expensive at $220,000 each, a mighty steep price in a neighborhood where some homes were going for as little as $20,000. The $80,000 that Comer’s foundation kicked in toward the price of each home wasn’t enough.

When too few residents stepped up, says Reid, “we worked with the University of Chicago to find families from outside Pocket Town who could move in,” aided by certain U. of C. grants. Reid began building the second round of 30 units in 2008, finishing two years later. (At the end of 2012, six homes remained unsold, and the last 30 of the 90 planned structures had not been built.)

The 2006–7 real-estate crash certainly didn’t help matters. “The housing crisis led to a disastrous foreclosure problem on the South Side,” says Geoff Smith, director of the Institute of Housing Studies at DePaul University. More than 30 percent of Pocket Town’s homes went into foreclosure; the vacancy rate is currently 16 percent.

New homes can improve a neighborhood only so much, Reid points out, when there aren’t many economic anchors at hand. Pocket Town contains only four businesses: a gas station, a paper supply company, an auto salvage yard, and Reid’s real-estate company. “There’s still no new retail, no grocery store, and there isn’t even a pharmacy,” he says. Without meaningful commercial activity in Pocket Town, building houses there “is no different than building in Englewood.”

Responds Schleicher: “We tried to identify how to bring in other businesses. . . . The problem is, the neighborhood is very isolated. You can’t attract big-box retailers or grocery stores, because they won’t reach a big enough market to make money.”

On paper, $86 million looks like a helluva lot of money. “But it’s really hard to change people and communities,” says Harvard’s Sampson. “We need to be realistic. . . . The social forces that permeate the South Side don’t stop at the Pocket Town boundaries.”

Furthermore, Sampson says, change depends heavily on a community’s ability to leverage it. That’s a skill that needs to be taught, not handed out. “In the beginning, people got comfortable with Gary giving out a lot of money,” says Binion, who left the youth center in 2009.

Schleicher admits that Comer and some of the foundation staff were overly optimistic. “We were businesspeople, not educators or developers. We thought we could have things changed within ten years. . . . Since we started, the neighborhood has changed, but not as much as we’d hoped for.” He adds, “We did some things right and some things wrong. Hopefully, our story will give the blueprint of lessons learned.”

One of the things Comer did do right, say experts, was to put most of his focus on education. Both Sampson and Knowles say that school reform can be a powerful tool to help revitalize struggling neighborhoods. Problem is, the investment can’t pay off for the community as a whole for many years. “The true test of the effort is to look at all the kids over time and see what their trajectory is,” says Knowles. “That just takes time.”

Luckily for Pocket Town, there is no time limit. Comer’s daughter, Stephanie, says: “We will never step back from the neighborhood. I bring my kids there so they can see what their grandfather built. And someday I hope they’ll want to support it as well.”