Wall Street to Main Street

Cindy Simon seems like a natural today, standing behind a podium in a posh ballroom, talking about business policies like workers’ compensation reform and bashing Gov. Gray Davis. But a year ago, she had never made a political speech, and this group -- the Conservative Order for Good Government, open only to registered Republicans -- would not have had her as a member.

Simon, a child of suburban Illinois and former Wall Street bond trader, was a Democrat until she switched to the GOP last year so she could vote for her husband, Bill Simon Jr., in the Republican primary for governor. Uneasy at first with his decision to run for office, she has thrown herself into the campaign with the same practical, hands-on enthusiasm that has marked many of her other unexpected turns. “When she embraces something,” Bill Simon said in an interview, “she does it enthusiastically.”

With a red, elephant-checkered scarf dangling around her neck, she tells the white-haired Conservative Order crowd that “family, faith and fitness” keep her going each day; that she needs her early-morning walks more than ever during the hurly-burly of campaigning; that California is falling apart under the Davis administration; and that the state is desperately in need of the expertise her husband can bring to Sacramento.

Afterward, the questions start on a high note. “At our table, we’ve decided you would make a great U.S. first lady,” says one man. Simon beams.

But soon, things get complicated. The next questioner says Simon’s husband looked bad in his debate against Davis, and a woman rises and asks for Bill Simon’s position “on the homosexual agenda and gay marriage.”

Simon freezes at the podium. It’s a touchy topic -- her husband was barraged with criticism for first pledging to back gay marriage, then reversing his position after his conservative supporters cried foul.

“I don’t really feel prepared to talk about that issue,” she says, hesitantly. But unlike a more experienced campaigner, she doesn’t let it end it there. “Bill is a man of inclusion.... We’ll get you that position. I’m not sure what it is.”

Simon, 47, likes to call herself her husband’s best advocate. “The person who seems even more comfortable on stage than Bill and seems able to communicate her effervescent personality is Cindy,” said John Morrissey, a friend and neighbor.

Until the campaign, her full-time job was raising their children: William, 14; Lindsay, 13; and Griffith, 10. Now she can spend 18-hour days on the road, sometimes holding more public appearances than her husband, whose campaign has been dogged by missteps. She wolfs down a sandwich or edamame beans before lunch speeches so she can talk to people. She describes it as a dream job for a biography junkie who devours obituaries because she is fascinated by people’s life stories.

“I feel privileged to meet all these people across the state,” Simon said in an interview. In an online journal she keeps for the campaign, she elaborates: “Was I really flying on Air Force One? Did I really share a joke with Condoleezza Rice? Was I really standing up there on the stage next to my husband Bill, hands clasped in front of me in nervous excitement, while he proudly proclaimed his victory speech on primary night?”

Woman of many roles

To her friends and family, Simon’s charm is that she has managed to play many roles while remaining the same down-home Illinois native who, after 12 years on L.A.’s Westside, still gets excited when she spots a celebrity at her local supermarket.

“While she’s been able to accomplish all these things and do all these incredible things, she’s still Cindy,” said her younger sister, Julie Head. “She’s just very natural and down to earth.”

Cynthia Louise Stewart was raised in Oak Park, a middle-class suburb of Chicago. Her father, Glen, was a manager at Sunbeam; her mother, Dorothy, worked briefly as a teacher but spent most of her time raising her three children.

Two forces dominated the household: local service and the basketball team at Indiana University, which every member of the Stewart clan had attended or would. The family gathered around the television during the season to root for Indiana; they also stood together at elevated-train stops to hand out fliers for Glen Stewart’s successful campaign for the local Parks Council.

At Indiana, Cindy majored in sociology. Many of her classmates were focused on getting jobs after graduation; she was more interested in learning about other people. It was pure happenstance that put her on a track to Wall Street.

The summer after her freshman year, Cindy joined her parents at a church picnic and met a representative from the financial firm Kidder Peabody. He offered her an internship in Chicago that paid 25 cents an hour more than her previous summer job, at the Schwinn bike factory.

Cindy was soon fascinated by investment banking and the energy coursing through the high-rises of Chicago’s financial district. She decided she would move to New York after graduation and pursue a career on Wall Street. She interviewed at Kidder Peabody her senior year.

It was 1977, and women were just entering the investment banking field. Cindy recalls the man who interviewed her at Kidder Peabody proposing that she start as a secretary and work her way up the ladder. “I said ‘No, no, no, I want to be on the trading desk,’ ” Simon recalled.

That’s where she ended up, and her reliability, level-headedness and attitude impressed many of her co-workers, including a young man named Peter Simon, one of two sons of Richard Nixon’s former Treasury secretary. “She came to New York City and came to a trading desk, the male chauvinist capital of the world at that point,” Peter Simon recalled in an interview. “She didn’t care. It’s not like she was arrogant, she was just, ‘Hey, I’m here to learn.’ ”

Because all members of the trading desk used the same phone lines, Cindy occasionally picked up calls from Peter’s older brother, Bill. At a Kidder Peabody party, Peter introduced his brother to Cindy. “I was introduced to her as, ‘Oh, this is Cindy that you’ve been talking to for years and years,’ ” Bill Simon recalled. “I remember thinking to myself, man, she’s cute.”

About a year later, in 1985, Cindy had just ended a relationship, and Peter leaped into action. He called his brother and told him that this was his chance. Bill made a date with Cindy, then realized it would conflict with a game in the NCAA basketball tournament’s Final Four. A sports fanatic, Bill kicked himself for not offering to meet her somewhere at 8 p.m., after the match, but gamely knocked on her door at the agreed-upon 6:30.

Cindy recalls answering the door: “Hey Bill, hi, it’s really great to see you, but can you wait a couple of minutes? Because I want to watch the rest of the basketball game.”

The couple married in Oak Park two years later. Soon after, Simon became pregnant with her first child. She took a maternity leave from her post, now vice president at Kidder Peabody, and never returned. Bill and Peter were about to go into business with their father, and someone needed to move from the East Coast to run the California office. Bill and Cindy went to Los Angeles to check it out.

“People used to say to me, ‘How long did it take you to get used to living in California?’” she said. “The 30 seconds it took me to get off the plane.”

Simon became a fixture in her Pacific Palisades neighborhood, throwing herself into local projects like beautifying son Willy’s elementary school and organizing coffee gatherings for parents there. She also helped her husband disburse some of the family fortune into charitable projects as a member of the Cindy and William E. Simon Charitable Foundation.

“She jumps in and she isn’t one of the people who says, ‘Let me write you a check and go away,’ ” said Donna Fol, a friend and neighbor. “She’ll go pull weeds in some area that’s being beautified.”

A ‘partnership’

In a speech to hundreds of local government officials at the Long Beach Convention Center last month, Bill Simon laid out a picture of his marriage.

“I take care of all the major decisions, and my wife takes care of everything else,” he said. “I define major decisions as: What is the family’s stance on the federal trade deficit? What is the family’s stance on national unemployment? What is the family’s stance on Taiwan? ... Everything else, I follow her lead.”

The line drew big laughs from the crowd, but friends say it is a pretty good description of the Simons’ home life. That has been apparent in the governor’s race.

Bill Simon told his wife about his interest in running during the winter holidays of 2000. Both knew it would mean a big change for the family.

“We really have this partnership, and I really felt it was important to him -- so let’s do it,” Cindy Simon said. “I could have easily said, ‘What are you talking about? We have this life.’ ”

Though she accompanied him on some early forays, Simon spent the first half of her husband’s campaign far from the public eye. She mostly stayed home and helped the kids with homework.

In the fall of 2000, when former Los Angeles Mayor Richard Riordan announced he wanted to be the Republican nominee for governor, some of Riordan’s supporters suggested that Simon should get out of the race or shoot for a lower office, like lieutenant governor or treasurer.

“Cindy said, ‘Nah, if you’re going to go for it, go for it,’ ” recalled Bill Simon. “She said, ‘You’ve just told everybody you want to be governor for a, b and c, and now you’re going to tell them you want to be lieutenant governor for e, f and g. Who’s going to believe you?’ ”

It was not until Bill Simon won the primary -- surging 60 points in the polls in two months -- that Cindy Simon truly saw what her husband was getting into. His siblings had flown in for the primary and the clan had dined at home in the Palisades, then crammed into a van and rode to the hotel outside LAX, where Bill Simon would declare victory before thousands of supporters and dozens of cameras.

“The kids were watching a movie on the video screen in the van, we were all excited and talking, then we turned that corner and saw what looked like hundreds of cameras,” Cindy Simon recalled. “There was a hush in the van, we all felt it.... Bill and I looked at each other and said, ‘OK, here we go.’ That was something you never, ever forget.”

Since then, Simon has had a steadily increasing role in the campaign. No longer does she spend her days taking care of her children’s schedules; now she relies on neighbors to carpool.

“This campaign has really showed me what life is like as a working mother,” she told a roundtable of Republican businesswomen in Long Beach.

Although she is enthusiastic about campaigning, Simon shies away from talk of politics. She is willing to acknowledge she is pro-choice -- something her husband, who opposes abortion, has cited as an example of how he is respectful of differing views on the issue -- but is hesitant to discuss her views on gay marriage or other areas where she may differ politically from her spouse.

“I certainly didn’t marry Bill because I’m exactly like him,” she said. “There’s so much more to Bill than a label.”

Her husband says that having Cindy on the trail has strengthened them both.

“Previously, I went to the office in the morning and went on business trips and she was home, and we would kind of hook up at night and chat about our respective days,” he said. “Now ... its kind of like we’re partners in an enterprise.”

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Times staff writer Matea Gold contributed to this report.