It’s midafternoon on a Monday, the sleepy part of a day, but mayoral candidate Gery Chico’s downtown campaign office hums: phones ring, aides bustle about, the candidate himself cradles a phone to his ear, dialing for dollars.

It’s an impressive operation—a large room filled with bright young staffers and volunteers eager to prove that Chico’s best suited to carry Chicago into the future.

And yet so much about the candidate is linked to the city’s past—and, especially, to Mayor Daley.

In the last 20 years, Chico’s been the mayor’s deputy chief of staff and chief of staff; he’s served as Daley’s president of the school board, park district, and, most recently, City College Board chairman. He’s used his contacts and experience with city officials and government to build a thriving legal practice that has helped win contracts and zoning approvals for clients—one of them being Alderman Ed Burke, the powerful longtime chair of the finance committee, who has also been a mentor to Chico.

Chico’s connection with Daley is a double-edged sword. He says his training and experience makes him the ideal successor to a political giant. “I’m ready to lead on day one” is his constant refrain. But the person responsible for Chico’s impressive resumé isn’t the most popular politician in these parts anymore—thanks largely to the $1.15 billion parking meter leasing deal he pushed through the city council in 2008, which has increased the cost of parking and left Chicagoans little to show for it.

Chico has negotiated a delicate balancing act in his campaign, taking as much credit as he can for Daley’s accomplishments while distancing himself from the bad stuff.

“I’m proud of the service I gave the city,” he says. “But I’m running for mayor. This is a new campaign.”

Chico’s ties to the Daley political organization date to 1978. As a 21-year-old junior at the University of Illinois’s Chicago campus, he walked into the 11th Ward Democratic headquarters looking for a city job. The 11th Ward was home to Daley and had been home to his father, Richard J. Daley, Chicago’s mayor from 1955 until his death in 1976. Chico and his family were living in the ward, at 33rd and Ashland.

His paternal grandfather, Encarnacion Chico, came to Chicago from Mexico in the 1920s and worked as a meat inspector in the stockyards. Chico’s father operated a print shop and a gas station on the southwest side; his mother, whose parents were Greek and Lithuanian, was a secretary for the UIC College of Dentistry. Chico is the oldest of three boys; the middle brother, Craig, is president and executive director of the Back of the Yards Neighborhood Council, and his youngest brother, Scott, is an engineer who lives out of state.

Chico graduated from Kelly High School in 1974. He mentions his public school background often in speeches and interviews. He also points out that his three children went to Chicago public schools. It helps distinguish him from Rahm Emanuel, who graduated from New Trier West High School in Wilmette and sends his three children to private schools.

During that visit to the 11th Ward office, he told the personnel director he was a political science major interested in government work. “They must have been impressed,” he says—because the visit led to an internship in the city’s planning department, and, eventually, a full-time job in the department’s industrial retention division. “I talked to business owners about what we can do to create more jobs in the industrial corridors.”

After two years in planning he took a job as a researcher for Alderman Wilson Frost, then chair of the city council’s finance committee. While working for Frost, he went to Loyola Law School at night; he received his degree in 1985.

In 1983 Harold Washington was elected mayor—the city’s first African-American to hold the office. That set off Council Wars, a legendary power struggle among aldermen. The 16 black aldermen and five white ones stuck with Washington. Aldermen Burke and Ed Vrdolyak put together an antiadministration bloc of 29 aldermen—28 whites and one Puerto Rican.

For nearly three years the Vrdolyak-Burke faction blocked Washington’s appointments and key legislation and tried to make his administration look incompetent, unfair to whites, and corrupt. The faction dumped Frost, who was black, from finance, replacing him with Burke. Burke kept Frost’s aide, Chico, on the job.

Burke didn’t return calls for comment, but other aldermen from that era remember Chico as a standout assistant when he worked for Burke. “He was bright—very bright—and very detail oriented,” says 50th Ward alderman Bernard Stone, who was a member of the Vrdolyak-Burke bloc. “Any bill that’s introduced, Burke researches it because it comes through his committee. And Gery would be doing the research for Burke.”

In 1986 four alderman loyal to Washington were elected, and he took control of the council. Alderman Tim Evans, a Washington supporter, replaced Burke as chair of finance. (After the younger Daley was elected in 1989, Burke regained the chairmanship, and he’s held it ever since.)

Chico says he wasn’t a partisan in Council Wars. Yes, he concedes, Burke is a political mentor and a close friend. But he’s quick to point out that Evans kept him on staff. “I didn’t like the racial divisiveness of Council Wars,” he says. “Anyone who knows me will tell you I can get along with everyone. At finance, I did my job and I did it well. I’m proud of the fact that I served in the finance committee for three different aldermen.”

In 1987 Chico left City Hall for a job with the corporate law firm Sidley & Austin. He mainly dealt with zoning matters, working under the guidance of Jack Guthman, then and now one of Chicago’s most prominent zoning lawyers.

“I knew Gery from his work at finance,” says Guthman. “He was just this hardworking, very knowledgeable guy. One day Ed Burke told me, ‘Gery Chico is ready to leave the public sector.'” Guthman called Chico, and soon Chico was working for him, representing developers who were seeking city approval for their projects.

City clerk Miguel del Valle, one of Chico’s opponents in the current race for mayor, has accused Chico of using his city hall connections to win deals for wealthy developers. Guthman says it didn’t happen that way. “It’s a negotiation between government and the private sector—no one gets everything they want,” he says. “You use someone who understands the process of government in Chicago. You have to understand the law, the zoning code, and all its nuance. Gery knows that. He knows it inside and out.”

In 1991 Chico returned to city hall when Daley asked him to work as a deputy to chief of staff David Mosena. Two years later Daley made Mosena aviation commissioner and promoted Chico to chief of staff. He held that job until 1995. Aldermen and reporters described him as inexhaustible and meticulous. Chico points out that his years as chief of staff predated the corruption scandals that engulfed city hall in the early 2000s.

In 1995 he left city hall to return to Sidley & Austin. A year later he moved on to Altheimer & Gray, a Chicago-based law firm that also had offices in Europe and Asia.

But he didn’t stop working for Mayor Daley. Just a few weeks after Chico announced he was leaving city hall, Daley named him president of the school board.

Chico’s six-year tenure at the school board is the keystone of his campaign today—testimony, he says, to his ability to lead and to handle complicated, formidable tasks.

In May 1995 the General Assembly gave Daley full control of the city’s schools. Besides making Chico board president, Daley named his former budget director, Paul Vallas, CEO.

Chico says he and Vallas took a notorious school system—labeled the worst in the nation by Education Secretary William Bennett in 1987—and transformed it into a national model.

Is his view accurate? When Chico and Vallas were in charge of the schools, I was one of their sharpest critics. I hammered away at them in my column for being autocratic and mean-spirited, and blasted them for a series of controversial personnel moves and policies that held back thousands of students who scored poorly on standardized achievement tests.

But their era—especially the first few years of it—also brought a remarkable energy to the schools. Awash with money thanks to a real estate boom as well as a new state law enabling them to spend property taxes, previously earmarked for teacher pension funds, in the general budget, they went on an unprecedented school renovation and rebuilding campaign. By Chico’s count, they rehabbed—or “I rehabbed,” as he often puts it now—more than 400 schools.

Chico and Vallas almost immediately signed a four-year contract with the Chicago Teachers Union, guaranteeing labor peace through 1999. They expanded preschool and after-school programs. They won over many north-side parents in the late 1990s by building two new selective-enrollment high schools—Walter Payton, at 1034 N. Wells, and Northside College Prep, at 5501 N. Kedzie. In 1998 they converted a former Catholic high school, St. Martin de Porres, at 250 E. 111th, into another high-achieving public high school, Southside College Prep (since renamed the Gwendolyn Brooks College Preparatory Academy).

Math and reading scores throughout the city climbed under Vallas and Chico, in part because they demanded that teachers spend more class time prepping their students for the tests. The mainstream media showered Vallas and Chico with praise bordering on adulation. Vallas and Chico helped shape Mayor Daley’s reputation as a public school visionary—a reputation he’s been flaunting ever since.

But in 2001 the scores started declining again, and Vallas and Chico fell out of Daley’s favor. Vallas and Chico were squabbling openly with each other, too. “They were oil and vinegar,” says Maribeth Vander Weele, the board’s inspector general then. “Different styles. Both incredibly hardworking, but Gery is more thoughtful, more respectful to his staff. Paul races at warp speed. Very creative, but much more impulsive.” Chico contends the media exaggerated the bickering between he and Vallas. Vallas has endorsed Chico’s mayoral bid, but didn’t return calls for this story.

Chico resigned from the board in June 2001, telling reporters he wanted to spend more time with his family: “When I’m at the 14th community meeting for the week and I’m not with my ten-year-old, going over homework, it takes a toll.” Vallas stepped down two weeks later.

Chico, of course, focuses on the positives of those six years: “We took a system that was considered one of the worst in the country and we turned it around. We’ve lost our way since that time. We’ve got to get it back.” He maintains that CPS leaders following he and Vallas—including CEOs Arne Duncan and Ron Huberman—mistakenly expanded the central office bureaucracy. He says he’ll shrink it and spend the savings in classrooms.

Researchers at the University of Chicago observed last year, in their book Organizing Schools for Improvement, that test scores had already begun to rise in Chicago’s elementary schools before the tough-testing policies of the Vallas-Chico years. Interpreting the test results from the late 1990s was difficult, the U. of C. researchers wrote, because of “considerable evidence” that “cheating” and “‘gaming the tests'” had increased along with the emphasis on test scores and the penalties for poor results.

In November Chico said the school system had “lost momentum” since he and Vallas left. Daley didn’t appreciate it. He wondered aloud to reporters why Chico had never talked with him about a loss of momentum. “He never, ever, ever, ever, ever, ever, ever mentioned that to me,” the mayor said. “I understand people are candidates. They will say a lot of things.”

The mayor’s snit may have been a blessing for Chico, giving him cred as an independent-minded politician not afraid to upset the powerful—even his patriarch.

Chico was determined to take advantage of his prominence as school board president. In July 2002, about a year after he left the board citing the need to spend more time with his family, he announced he was running in the 2004 Democratic primary for U.S. Senate. But he was trounced by Barack Obama, winning only 7 percent of the vote in Chicago, where he’d hoped to run strongest, and finishing fifth in a field of seven.

In the summer of 2003, Chico’s law firm, Altheimer & Gray, declared bankruptcy and folded. Chico, the firm’s managing partner at the time, was criticized by other lawyers in the firm for expanding into foreign markets that didn’t generate nearly enough business to pay the bills. But Robert Berger, who was with the firm then, defends Chico: “I was part of the executive committee—I know what happened. The dot-com bubble burst. There was 9/11. The economy went into recession. It’s the sort of thing that happens to law firms a lot. I support Gery for mayor.”

Eventually Chico and the firm’s 58 other equity partners had to pay $15.6 million to cover the defunct law firm’s debts.

Chico doesn’t like to discuss the firm’s demise. In the totality of his career, he says, the bankruptcy was a speed bump. “I learned lessons and I moved on,” he says. “These were hard economic times.”

In the months after Altheimer closed he and Marcus Nunes, a former CPS lawyer, formed Chico & Nunes, which has grown into one of the largest Hispanic-owned law firms in the city, with 15 lawyers. It’s a registered lobbyist for 40 companies, including Cisco System, Exelon, and Clear Channel. In 2009 Chico and his second wife, Sunny Chico, who runs a consulting firm that provides tutoring services and curriculum advice for school systems, made $2.6 million, according to their tax returns. The couple lives in the South Loop.

Chico says he’ll quit his firm if he’s elected, but he won’t require it to discontinue its City Hall lobbying: “I can’t tell a law firm what to do.” To eliminate the appearance of a conflict of interest, he’d bar the firm from receiving city contracts. Chico adds that he’d award all contracts by competitive bidding, even those for bond deals. Daley awards bond deal contracts to firms without competitive bidding.

In 2007 Daley appointed Chico president of the Chicago Park District. Chico supported the mayor on all of his controversial park proposals, including moving the Children’s Museum from Navy Pier to Grant Park, building a soccer field in Lincoln Park that the private Latin School had primary access to, and the pledge, during the city’s ultimately unsuccessful bid for the 2016 Olympics, to turn over several parks to the games. (Legal proceedings have stalled the Children’s Museum move, and in December Chico said that if he’s elected he’ll try to keep the museum at Navy Pier or find a site for it other than Grant Park.)

Last March, at the mayor’s request, Chico left the park district to become chairman of the City Colleges board. But his tenure there was brief. On September 7, Daley announced he wouldn’t seek reelection. Two weeks later Chico stepped down from the board to run for mayor.

Despite his years in the seat of Chicago power, Chico has few endorsements from top local pols. Mayor Daley’s not endorsing anyone. Last week Alderman Burke announced that he backed Chico. Burke pointed to Chico’s experience in city government and added that he was well liked by aldermen. But asked by Fran Spielman of the Sun-Times if this was an endorsement, Burke stopped short: “What’s an endorsement? I support Gery Chico. I’m happy to be his friend. . . . It is what it is.”

The scuttlebutt among aldermen and other city hall insiders is that Burke is quietly supporting the legal challenge to Rahm Emanuel’s residency—and that Chico wants to keep his distance from that challenge, which has been criticized by both the Tribune and the Sun-Times. The Board of Elections Commissioners ruled in December that Emanuel can run for mayor, and a circuit judge has upheld that ruling; Burt Odelson, the lawyer challenging Emanuel’s residency, has asked the Illinois Appellate Court to intervene. Once the case is resolved, look for Burke to come out strongly for Chico. Incidentally, the case may ultimately be decided by the Illinois Supreme Court, which includes Justice Anne Burke—the alderman’s wife.

I talked with Chico recently in the cafeteria downstairs from his campaign office at 333 W. Wacker. As usual, he was meticulously attired—conservative white shirt, blue tie, blue suit. I asked him first about Council Wars—the city council battles when Harold Washington was mayor.

“You had a bunch of white racist aldermen—and you went with the bigots,” I said. “What was that all about?”

He smiled and dug a fork into his salad. “It was not all black and white.”

“Please explain what was not black or white about Council Wars.”

“At that time I needed a job,” he said. “You ask anybody about me—I was always fair. Don’t forget—I worked for Frost before I worked for Burke. And I worked for Evans after I worked for Burke. My strength is my ability to relate to all people.”

I asked about the parking meter deal. “You criticize it now; why didn’t you criticize it before Daley rammed it through the council in 2008?”

“Do I think it’s a bad deal? Yes, of course,” Chico responded. “But I was not in a position to vote against it.”

“And the Tax Increment Financing programs—as school board president you signed on to the creation of dozens of TIF districts.”

TIF needs to be more transparent, he said, “but you don’t want to throw out the baby with the bathwater.”

My translation: He knows that TIF gives the mayor almost free rein over at least $500 million a year in property taxes, and he’s not about to relinquish that.

He said it all succinctly in a gravelly voice, as if he were already the mayor, issuing the sound bite of the day.

As he likes to put it, he’s ready to lead on day one. For better and worse, he’s been on the inside for the last 20 years.