Being the Boss: Richard M. Daley runs a seemingly unstoppable political machine that's figured out how to win big support among Chicago's Black and Latino majority. But what has he done for them?

In 1993, Madeline Haithcock was appointed alderman of Chicago's 2nd Ward, a mostly Black area that included up-and-coming neighborhoods on the south end of the Loop. The position was open because Bobby Rush, a former Black Panther and longtime social activist, had just been elected to Congress, and as the ward's reigning political figure, he had dibs on picking a successor. Haithcock wasn't well known, but the choice made political sense. She had proven her commitment by volunteering for Rush's ward organization; she was considered pleasant and pliant; and she was African American--all of which seemingly made her the perfect guardian of Rush's home base.

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Rush had some reason to be protective. Richard M. Daley, four years after his election as mayor, was successfully courting--critics would say co-opting--some of the city's most respected Black leaders, offering city services and contracts to woo ministers, heads of community organizations and even other aldermen, who not long before had sworn they were committed members of the city's independent movement.

No one had to remind Rush that the new mayor was the son and namesake of the old Boss Daley; it was national news, confirmation of a political dynasty in the third-largest city in the United States. But for Chicago's progressives, returning to the rule of another Daley was an unmitigated disaster, a sign that the racially divided city had again reverted to an era when a select few white men, with help from their friends and lackeys, ran the show. Rush, on the other hand, wasn't going to be bought off or cut out; he would control a slice of the city. He would position himself to counter the Daley forces.

But within two years, his plan backfired.

Haithcock resented Rush's attempts to control the ward and to control her--she claimed he ordered her to fax him copies of her daily schedules--and they had a public falling out. In 1995, Rush's sister ran against Haithcock. And when Haithcock turned to Daley for help, the mayor delivered, dispatching city workers to the ward to convince voters to punch the ballot for Haithcock. She won.

A decade later, Haithcock's ward is one of the fastest-developing parts of the city, and she has become a reliable Daley vote in council meetings. Rush doesn't say much about city issues.

And Daley now wins big majorities in Black and Latino wards, just as he does across the rest of the city.

Haithcock said she knows why. "He's different from his father," she said. "It's a different time."

Boss the First and Second

For a while this spring, every passing day seemed to bring another commemoration of the 21-year mayoral reign of Richard J. Daley. The first Boss was sworn in 50 years ago this April, and to honor the anniversary, elected officials, journalists, historians and political scientists in Chicago gathered to reflect on his leadership.

As is customary at those kinds of events, only the highlights were recounted: Daley won the presidency for John F. Kennedy; Lyndon Johnson consulted him regularly; and well into the 1970s, no one would think to make a run for the White House without trying to win his endorsement. At home, Daley's name and face were plastered on signs and public works projects across Chicago, which grew into a world-class city because of his vigor for building highways, skyscrapers and convention centers. Maybe Richard J. Daley ruled Chicago like a satrap, but at least his city "worked."

Far fewer observers brought up the stuff that wasn't quite as flattering, such as the fact that, between 1955 and 1976, the first Mayor Daley evolved into the nation's preeminent symbol of northern segregation. In 1966, he stood down Martin Luther King Jr., insisting that Chicago didn't have any ghettos and implying that the civil rights leader should stay down South where he belonged. Two years later, Daley ordered police to "shoot to kill" when parts of the city exploded in riots after King's assassination. For a generation, he consistently presided over plantation politics, school segregation and public housing isolation.

These discussions also had an interesting side effect. While buffing the image of the first Mayor Daley, they focused considerable attention on the current one, who already seemed to be attracting a spotlight.

Suddenly, after 16 years in office, Mayor Richard M. Daley is getting national attention again. Time magazine, for example, recently named him one of the top mayors in the country, citing his "near imperial power" as the primary reason for Chicago's "transition from graying hub to vibrant boomtown."

Some of this is undeniable. Not only is the Loop bustling and beautiful, but, as Time noted, Daley also has led a massive redevelopment of dilapidated public housing complexes, ordered a radical reorganization of the public schools and overseen a residential building boom unparalleled in the Rust Belt, if not in the country.

But just as key episodes have sometimes been omitted from his father's story, part of the story of Boss the Second, and perhaps the most important part, has barely received a mention. Richard M. Daley is not just a powerful politician--he's a powerful white politician. He's the son of the man whose racial record people like Bobby Rush and even Madeline Haithcock have said they're working to undo. He's a guy who is often praised in communities of color by people who emphasize that he is not his father.

He's also a guy who seems to be defying national trends. While a diverse, liberal coalition of Los Angeles voters elected Antonio Villaraigosa their first Latino mayor this spring, the second Mayor Daley has actually consolidated power as Chicago's white population has shrunk. As of 2000, the city was about 31 percent white, about 36 percent Black and 26 percent Latino. In his re-election two years ago, Daley seized almost four of every five votes cast in beating three relatively unknown Black opponents.

For mainstream liberals and the national media, Daley is the unlikely model of an effective and racially sophisticated new white leader--one who surrounds himself with smart, fresh-thinking people of diverse racial backgrounds and who works with them to make sure that every single neighborhood in Chicago has affordable homes, accessible jobs and good schools.

Yet his critics point to the mayor as a brilliantly manipulative racial politician--somebody who knows how to co-opt Black preachers and Latino businessmen, who lets his friends of all backgrounds get rich off the public dime and who crushes even the first hint of an independent movement.

The two views may seem to be at odds, but they're both part of the story of Richard M. Daley, an old-school Chicago mayor who's figured out a way to make his political machine subtle, efficient, powerful and--perhaps most crucially--diverse.

Spread the Spoils

In mid-May, Daley held a press conference outside an abandoned tavern in a mixed-race ward on the Northwest side. His unique political skills were all on display. Surrounded by the ward's alderman, Rey Colon, and a racially mixed group of aldermen and area homeowners, the mayor made a few remarks denouncing irresponsible bar owners who, he said, had let their businesses become outposts of drug dealing and violence. His face was red and sweating and often contorted into a look of disgust, and his speech was full of mispronounced words and odd tangents--a fairly inarticulate, populist style that the people gathered around him seemed to accept as evidence that he was, at heart, a regular neighborhood guy who cared.

Business owners need to respect their neighbors, he said. Some of them "sell a bill of goods. They say they're opening a restaurant. All the sudden they're selling hamburgers, they're selling their hot dogs, their grilled cheeses, and all the sudden it's a night club."

The logic may have been hard to follow, but everyone knew what he was going for. He was on the side of the working-class folks who don't want to live next to seedy night clubs, and he was proposing a law that would give them power to shut such places down.

Subsequent questions from reporters about misspent street repair funds were directed to an aide, the Latino transportation commissioner, and didn't seem to have much of an impression on the young Latinos who waited to shake Daley's hand as he made his way to his chauffeured car.

One of the teenagers, a clean-cut former gang member handing out anti-violence bumper stickers, said he thought the mayor was serious about reducing crime in the neighborhood. And he didn't care that Daley is white. "As long as the leadership is good, it doesn't matter," he said.

That point of view is common among Daley supporters and opponents alike. But those in the mayor's camp often take the argument further. They say that Daley is a good leader because he consciously tries to include diverse viewpoints in his decisions.

"He has reached out to people of all backgrounds and cultures, and he has been unyielding in his dedication to be fair to everyone," said Jackie Heard, the mayor's press secretary, an African American who grew up in public housing.

City Councilman Ed Smith was reluctant to sign on to the mayor's proposed budget a few years ago. Among other things, he wanted more funds for rebuilding city streets in his impoverished West Side ward. Then Daley aides sought him out to see if they could forge a compromise. "The one thing this administration has done is talk to you," said Smith, an African American who has held his city council seat for 20 years. "We didn't get all we wanted, but we got some of it."

Under Richard J. Daley, favored aldermen and favored wards were known to receive more and better city services than the areas that wouldn't give him big election numbers. But the Second Boss has brought a different approach: spread the spoils around and become a good guy in as many people's eyes as possible.

That's what he's tried in the West Side's 37th Ward. A run-down, predominantly Black area, the ward has been starved for investment for a generation. But a few years ago, the city built a new library there, and last summer, the city council, with Daley's support, voted to allow construction of the city's first Wal-Mart on the site of one of the ward's abandoned factories.

Since the mid-'90s, the Daley administration has handed each of the city's 50 aldermen a chunk of money, now up to $1.2 million a year, to use on street and sidewalk repairs of their choice.

The aldermanic menu program, as it's known, has made lots of people happy. Daley still controls the city's purse strings, but aldermen get some say in their own share of the money, and voters are impressed when they see the city at work on their blocks.

Transforming the Projects

Still, arguably the biggest symbol of change under this Daley has been implemented in the city's public housing communities, which are almost entirely Black. Chicago's high-rise "projects" were once nationwide symbols of racial and economic isolation--crumbling structures where poor single mothers and their children had to navigate drug dealing and violence daily.

But the complexes are now in the middle of a controversial ten-year, $5 billion "transformation" program that will see the high-rises torn down and mixed-income row houses and condominiums built in their place. Already, the bleak rows of concrete tenements that once lined Interstate 94 on the South Side are mostly gone, and other areas, such as Cabrini-Green on the North Side, don't look anything like they did just five years ago, before construction of the new townhomes, grocery store, police station and park. Former residents are living in private-market apartments and undergoing job training programs if they haven't already found work.

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"It sounds pretty good," said William Wilen, a longtime public housing advocate who serves as director of housing litigation at the Sargent Shriver National Center on Poverty Law. "There's really no dispute that the [public housing] system had failed, and something had to be done, and something is being done. But the devil is in the details, and few people know the details."

From Wilen's vantage point, the details are disastrous. At most of the city's public housing developments, officials moved residents out of their homes--where many had lived their entire lives--and into private-market apartments miles away. The city's explanation was that families would be offsite while demolition and reconstruction occurred and then granted the right to return. But studies have shown that most ended up in run-down apartments in neighborhoods as depressed as the ones they left. Children were often far from their schools and thrown into new gang turf. Social service programs still haven't reached many of the families most in need.

In addition, while Wilen estimates that 80 percent of the former residents want to move back to the rebuilt developments, they'll need to have 30-hour-a-week jobs, good credit and clean criminal records to get approved--requirements that are all but impossible for many single parents and others who have never worked.

Wilen said that many residents may end up staying in the inadequate private apartments that were supposed to be temporary. Others point out that the new buildings simply won't have enough units to house everyone who used to live in public housing.

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"Families segregated by the first Mayor Daley are being re-segregated by the second Mayor Daley," said Wilen, who is white.

Critics of the transformation maintain that the city should have rebuilt developments in stages, so that families could have moved from building to building in their own neighborhoods instead of being relocated across the city. And others worry that the plan is an excuse to gentrify areas that have become valuable in the years since public housing went up.

A recent, unusual outburst at city hall exposed increasing doubts about the transformation plan. In a routine city council committee meeting, South Side Alderman Carrie Austin, usually one of the safe African-American council votes for Daley, briefly stalled approval of a few minor real estate transactions related to new construction at a public housing site. Developments in her ward weren't well thought out, she said, and too many former public housing residents lacked the help they needed. The head of the Chicago Housing Authority, Terry Peterson, "may be doing a fine job in some places, but on the far South Side, he is doing a piss poor ass job," Austin declared. She voted against the items, they were approved anyway.

Gentrification or Education?

Ten years ago, Daley pressed the Illinois legislature for management control over the struggling Chicago Public Schools, a system of 600 schools and nearly 450,000 students, 91 percent of whom are of color. He got his wish. Under the two Daley-appointed teams that have led the schools since then, test scores across the district have improved, the pace of school construction has picked up and more administrators have been held accountable for poor performance. The system is no longer known as "the worst in the nation," as former Education Secretary William Bennett called it in the late 1980s.

But that doesn't mean the district is up to par yet. Test scores began leveling off a couple of years ago, even as some parents and advocates complained that teachers were spending too much time on test preparation and not enough on other basic skills. Budget crunches are an annual ritual, and many schools are still in dire need of repairs.

Dissatisfied with the rate of progress, Daley announced another school reform plan last summer. Under Renaissance 2010, as it's known, perennially failing schools will be shuttered and then reopened, starting this fall, with new curricula and staffs. While remaining part of the public school system, these programs will be free of the regulations that bind regular neighborhood schools. Outside groups--nonprofit charter school companies, area universities, even social service organizations--will develop the schools in coordination with district officials, often around particular themes or philosophies.

One of the new institutions, Bronzeville Lighthouse Charter School, will take over what used to be Hartigan School, a South Side elementary school that served children from a nearby public housing development. Mark Culliton, one of the leaders of Lighthouse Academics, the Massachussetts-based nonprofit that's developing the charter school, said neighborhood families are already excited about its arts-based approach to learning, though it won't open until fall 2006. In two days of modest recruiting at local community centers and shopping strips, Lighthouse collected the names of 300 interested parents, he said. And leaders of public housing residents' groups and other community organizations have joined the school's board of directors.

"Our fundamental belief is that just because you're poor or live in a certain neighborhood, doesn't mean you shouldn't get an excellent education," Culliton said.

Others see the Renaissance 2010 plan as the wrong move. "Supposedly, the idea is to replace failing schools with better ones. But they're putting in place schools that have no track record or very little track record," said Julie Woestehoff, the executive director of Parents United for Responsible Education, a school reform group. "We think that Renaissance 2010 has more to do with gentrification than education."

She argues that because most of the new schools will be created in hot real estate areas, they'll mostly help to accelerate the demographic changes. "The mayor has been very clear about his goals for the system--to make it attractive for middle-class families," she said. "But that's not parents' goal. Their goal is to make sure every child is educated, not just those from the middle class."

Culliton dismisses such criticisms, arguing that the school system would be wrong not to try new approaches. "I'd ask that person what they'd do with the woeful lack, the criminal lack, of educational opportunities for poor children in Chicago. Do you want to stick with the status quo? Because the system is clearly broken now," he said.

Woestehoff agrees with that part but maintains that, rather than spending money on untested approaches, the district should work to replicate "dozens" of its schools that are already offering an excellent education. The problem right now, in her view, is that the best-funded, best-run schools, with the best books, facilities and teachers, aren't serving the city's neediest students.

"CPS knows how to run a good school--they've done it," Woestehoff said. "But the mayor did not take over the school system to improve the lot of African-American and Latino kids. He took over the schools to attract middle-income families. So the result you're going to get is continued oppression of low-income communities."

An Arguably Corrupt Operation

For years, Daley has pledged his support for affirmative action in the form of the city's minority contracting program, under which 25 percent of all city business is supposed to go to minority-owned firms and five percent to companies owned by women.

The city has met its overall targets, but news that only nine percent of last year's contracts went to Black-led firms infuriated many African-American leaders.

Recent headlines haven't improved the picture for Daley. In the last several months, the daily newspapers have uncovered evidence that at least a few high-profile, white-led businesses fraudulently posed as minority-owned to win millions of dollars in city contracts. And federal investigators recently seized files from several city departments, part of a major look into corruption in an administration program that paid private trucking firms for work they didn't do.

"Because the mayor has grown up in an environment where it's a norm, I don't always think he can see the corruption," said Colon, the alderman from the Northwest side. "Somebody like me, who's from the outside, it's easy to see how we've been shut out ... Until we have a minority in that position, it won't change."

The corruption investigations have shown that taxpayer money has been misused. But that's not all--they've also started to pull the lid off Daley's seemingly unstoppable, and arguably corrupt, political operation.

According to federal authorities, the leader of the Hired Truck program was a former gang member with ties to the Hispanic Democratic Organization, a potent political operation led by two of Daley's top lieutenants, who are also Latino. The HDO rank and file is made up of city and county workers who owe their jobs to Daley insiders. At election time, they're sent out across the city to knock on doors, hand out literature, monitor polls and, some charge, intimidate voters. In the last eight years, a series of Latino independents has been targeted and beaten by the HDO, sending a "chill," in the words of one survivor, across Latino parts of the city.

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Some insiders say Daley dispatches other city workers into Black neighborhoods. Black aldermen say they're asked to go to work for other Daley-allied colleagues who may be in trouble. Others note that the mayor has employed a full-time staff member to court the support of African-American clergy, sometimes by helping them win city tax credits, buy vacant lots or receive grants for social service programs. With the extra resources, the churches offer ministries that help thousands of needy residents, but critics charge that, in return, they're obligated to use their pulpits to get out the vote for Daley.

Supporters call it outreach; opponents call it a buy-off. The implication is that people have to play by Daley's rules if they want in at all.

"Daley has a lot of money and a separate organization that he can send into any ward. You've created a Democratic Party within the Democratic Party," said Robert Shaw, a former alderman and Cook County official who's been involved in local politics for more than 40 years.

"This mayor seems to have co-opted all of the ideas the independents have," said Shaw, who is African American. "Daley has the power."

Only Game in Town

Shaw said he thinks Daley has implemented a "superb" political strategy. But others blast the mayor for failing to invest in African-American areas the way he has downtown. And they are particularly dismissive of his Black and Latino allies, whom they openly call sellouts.

"Every alderman has a pet project in his ward, and the mayor makes that happen," added William "Dock" Walls, a longtime political activist who's contemplating a campaign against Daley in 2007. "They cower down and allow him to dictate the pace rather than being an elective body."

Walls and other Daley opponents say the city could be run more equitably. They argue that the aldermanic menu program may have appeased complacent council members and even a fair number of voters, but it hasn't done much to reverse the decline of the city's poorest neighborhoods, which still have the highest unemployment and crime rates, worst schools and most inadequate housing. In fact, studies show the neighborhoods in and around the Loop still get a disproportionate share of public money.

Walls thinks plenty of like-minded people are out there. "They're locked into Daley [right now] because he's the only game in town."

Election numbers suggest he may be on to something. Though Daley won 79 percent of the ballots in 2003 against three long-shot candidates, he received about 100,000 fewer votes than he had 12 years earlier. Apathy, as much as Black and Latino support, has kept him in office.

Insiders know this. It's why, even as Daley wins national awards and glowing p.r., Walls isn't the only upstart considering a challenge. Some big names--including U.S. Reps. Jesse Jackson Jr., Danny Davis, also an African American, and Luis Gutierrez, a Latino--are reportedly lining up supporters even as they publicly state they're not mayoral candidates--at this time.

Naturally, everyone has an opinion about each of their chances. But no one really knows whether the Daley Machine can be stopped or whether anyone else can create a rival operation that draws in so many different people.

Mick Dumke is a contributing editor for the Chicago Reporter. He also teaches journalism at Columbia College Chicago.