Paula Wolff was born in 1945 in Washington, D.C., the second of three children (two girls and one boy) to Jesse and Elizabeth Wolff. Her father is a corporate lawyer for a Manhattan law firm; her mother stayed at home and raised the family. She grew up in Mamaroneck, a Westchester County suburb. She attended public schools until her sophomore year, when her parents “decided I needed to learn to punctuate and spell” and enrolled her at Rye Country Day, a private school for girls. She graduated with honors.

She’s Jewish, but like her parents does not practice the faith. Her mother volunteered in Adlai Stevenson’s presidential campaigns, but the family was not politically obsessed. Young Paula read the newspapers, but she was not the kind of kid who knew her congressman’s name.

She kept busy. “In high school, I had the same pathology then as I have now–I like to do too much. I wanted to be on the cheerleading squad and I wanted to play sports. I was on the basketball team. I studied a lot.

“I read everything that anyone would hand me. I went through my J.D. Salinger stage. I got into a jag with [Italian playwright and novelist] Luigi Pirandello. I liked his themes. As far as he was concerned, there might be no reality. It certainly gives you a lot of latitude when your parents are disciplining you. You can always say, ‘Dad, Mom–for all I know we aren’t even here.'”

In the fall of 1963 she went to Smith College, in Northampton, Massachusetts, the same private women’s school her mother had attended. She majored in government, and studied under political theorist Leo Weinstein. “Weinstein told us that to understand government you must understand that simply writing about who votes how on what issue does not tell you the whole story. You have to understand what motivates people to act, what values they are following. If issues are important enough to people, they aren’t going to be stopped by the fact that they don’t have enough votes.”

The civil rights movement was cresting, and many of Wolff’s peers headed south to teach in freedom schools. She thought about joining them, but didn’t. A few activists organized a chapter of the Students for a Democratic Society at Smith, but she didn’t join them either. She opposed the war, but was not deeply involved in the antiwar movement.

She did organize a group called CRASH (the Committee to Reevaluate and Assess the Smith Handbook). As a result of their protests, the college relaxed its rules and permitted women to close their doors when men visited their rooms.

She was senior class president.

“I thought about taking the law boards, but when I asked my father for advice he told me that his firm didn’t hire women. He said, ‘We can’t, because this is a service position’–meaning the clients will not accept it.”

So she enrolled in the University of Chicago’s graduate department of political science and studied under Weinstein’s mentor, the legendary political philosopher Leo Strauss. “I was in culture shock, coming out of an all-girl school where the downside is that it’s a very artificial social environment in which you don’t live in the reality of the double gender world. On the other hand, having gone to an all-girl school, I had no reason to think that men were smarter than women, even though most men at Chicago–and most women, to a degree–had been conditioned to believe that was the case.”

She supported Eugene McCarthy in the 1968 presidential primary, but voted Republican in local elections (“the Democrats offered no decent alternatives; it was all machine”). She intended to teach political science at a college in Alabama for a year, but the school ran out of money and couldn’t hire her.

Instead, she got a job through a connection as a budget analyst for Governor Richard Ogilvie; by the summer of 1969 she was Ogilvie’s liaison to the Constitutional Convention, the assembly of delegates elected to rewrite the state’s constitution. Among the delegates was Wayne Whalen. They were married eight months after they met.

He was a corporate lawyer and a liberal Democrat who joined forces with Jesse Jackson and Billy Singer and led the legal battle to oust Mayor Richard J. Daley from the 1972 Democratic National Convention. Wolff and Whalen were part of a growing legion of young, idealistic liberals gathering in Chicago. They believed in integration. They settled in Hyde Park. They fought the Daley Machine, but they did it by institutional means. They filed lawsuits and wrote position papers for opposition candidates. They didn’t take to the streets. They worked hard at their jobs and got good at what they did.

The first of their four children was born in 1973, one year after she earned her PhD. “I took my orals while my baby was kicking inside me, which made it seem all so irrelevant.”

Her dissertation was on the Constitutional Convention and observed how many of the delegates had had to abandon or compromise their principles in order “to produce a workable document.” After that she taught public service at Governors State University, and in 1976 was named staff director of a bipartisan panel on reorganizing state government. Impressed by her efforts, an aide to James Thompson asked her in 1976 to work on the governor-elect’s transition team.

There she was at age 31, putting together the governor’s administration, choosing among men and women older than herself who would run the state.

“I had just finished studying the reorganization of state government so I knew its structure,” says Wolff. “You had to know what to ask each job candidate. In Public Aid, for instance, a lot of money had been misspent and the federal government wanted it back. So you wanted someone who knew a lot about the federal government. At the Illinois Commerce Commission you wanted a balanced group–so all views would be heard, but not so polarized that they couldn’t get anything done.”

She was cool and quick on her feet. As one coworker put it, “She doesn’t often fight a fight she doesn’t know she can win in advance.” According to reporter Kathleen Best’s article in Illinois Issues, “she requires her staff each year to develop lists of nettlesome, long-term questions with no simple, short-term answers. The lists–dubbed the ‘parade of the horribles’ and depicted as creeping slugs on purple staff T-shirts–are for those nights when people awake at 2 a.m. and ask themselves what they’ve done lately ‘that’s good for government.'”

Most of all, she was smart, far smarter than the average state bureaucrat. It wasn’t just street smarts–there were plenty of ambitious lawyers who had those. It was that, well, she knew about Pirandello. She added a little class to an operation that otherwise consisted of humorless ex-prosecutors and party hacks out of Du Page County.

Thompson made her his “program coordinator.” For the next 14 years she wrote budgets, settled crises, and helped oversee every program the governor implemented. She was known as “Thompson’s conscience”–a dubious distinction, since Thompson was known for cutting funds for public education, general assistance, and other programs for the poor.

In the meantime, her husband’s career took off. He helped open the Chicago office of the New York-based law firm Skadden, Arps, Slate, Meagher & Flom. They specialized in corporate mergers and acquisitions. They made millions.

Before too long, Paula and Wayne had made friends and allies in every mainstream political circle. Their children attended school with the children of Richard M. Daley; Wolff and Maggie Daley served together on that school’s board. Al Raby lived with them in 1983, while he managed Harold Washington’s historic mayoral race. (At the same time Jim Fletcher, one of Wolff’s cohorts from the Thompson administration, ran Bernie Epton’s campaign.) In 1989, Daley tabbed Whalen’s law partner, John Schmidt, to oversee his transition as mayor. Wolff did the same job for Jim Edgar last year after he was elected governor.

Throughout her tenure with the state, Wolff worked long hours–up at five, home at eight–often flying to and from Springfield in a single day. “I don’t go to a lot of parties,” says Wolff. “That’s the time I like to spend with my kids.”

For her efforts, her colleagues showered her with praise. She’s “smart, she’s tough, she’s practical, she’s pragmatic,” said Thompson in the Illinois Issues profile. “Paula is one of the most talented people I have ever met in government.”

Marilyn Katz, a local publicist who supported Wolff’s campaign for chancellor, goes beyond that: “She’s brilliant.”

Such was the buildup that preceded my only meeting with Paula Wolff. It took place in her husband’s 21st-floor office. She wore blue jeans and seemed relaxed. She was witty in a wry sort of way, but also evasive and discreet. I tried every which way to get her to reveal a trace of her ideas or ideology, but she would have none of it.

“Are you a liberal or a conservative?” I asked.

“I don’t believe in labels.”

“Who did you vote for for president?”

“I won’t tell you.”

“You won’t tell me?”

“It’s a private matter.”

“Does your husband know who you vote for?”

“I don’t know.”

“How about your kids?”

“At various times I’ve taken them into the polling booth with me, but I’m sure they’ve forgotten who I voted for.”

“What is your opinion of the Black Panthers?”

“I don’t remember having any opinion about them–although I was outraged by the slaying of Fred Hampton.”

“Were you excited about Harold Washington’s victory?”

“Didn’t you find it exciting?”

“Yeah, but it must have been incredibly exciting for you, what with Al Raby staying in your house.”

“It was an exciting time for everyone. I’m sure Bernie Epton thought it was very exciting too.”

“You’re amazing. I’m asking you all these questions and you’re not revealing anything about yourself.”

She smiled. “That’s not true; I revealed that I was a member of CRASH.”

“What do you think about the critics who say that you and Thompson didn’t do enough for social programs?”

“You have two choices: raise taxes or control spending. Thompson tried both ways. In any budget you’re making trade-offs. I’ve never been part of a budget process that wasn’t wrenching.”

“What about critics who say Thompson spent too much money building jails and not enough on schools?”

“If you have a court saying you can’t triple-cell prisoners and you are incarcerating more prisoners, you have to build more prisons.”

“But critics say that before Thompson, the public schools got something like 48 percent of their funding from the state and now it’s only 38 percent. Which means the schools are more dependent on the local property tax.”

“I’m not sure the numbers are as bad as the education professionals make them out to be. To me the important question is, what are you getting out of the education system? Does more money give you more? Not if it’s poorly spent.”

“Are you mad at your critics?”

“I don’t get angry. I don’t think you win by raising your voice.”

“How do you win?”

“You win by figuring out how to win.”

“What are you going to do now?”

“I’m teaching a course at the University of Chicago; I’ve had a few offers but nothing I really want. I was tremendously disappointed by what happened [with UIC]. I really wanted that job. But I’ll move on. There will be something else.”

Art accompanying story in printed newspaper (not available in this archive): photo/Kathy Richland.