Simon an Eager but Rookie Politician

Bill Simon Jr. is flashing that Boy Scout grin again, the one that’s a yard wide and makes you wonder if he swallowed a happy pill. He has just wrapped up a speech to a group of Republican women here, and their standing ovation has left him pumped.

Cornering his press secretary, the GOP candidate asks the question he asks after every stop on his long-odds journey to become California’s next governor: “How did I do?”

The aide shrugs, having heard only bits and pieces of the talk. So Simon--looking hopeful, craving feedback--turns to a reporter: “What did you think? I’ve reworked it a little, tried some new stuff. . . . Was it better than the last time you saw me?”

In a world dominated by cocksure, battle-tested politicians, Bill Simon is an eager, earnest work in progress, openly delighting in every stage of his maiden campaign.

He listens to old Ronald Reagan radio addresses in his car, works the cell phone while on the treadmill, huddles with a “brain trust” he assembled for policy advice, studies tapes of past gubernatorial debates--and tries to learn Spanish on the side. If the wealthy Los Angeles investor loses to a Republican rival March 5, it won’t be for lack of trying.

But Simon must win over an electorate that has proved itself leery of rich political newcomers--guys like Democrat Al Checchi, who had brains and $40 million in 1998 but couldn’t derail the Gray Davis train. Critics call Simon a Checchi rerun, right down to his failure to vote in three recent elections. They say only hubris--or political naivete--would drive him to seek the governorship on his very first shot at elected office.

Simon’s friends and family insist the cheerful, unpretentious man they call Billy is different. He most certainly is not, they say, a restless master of the universe out to conquer yet another mountain. Rather, he is driven by an ethic of public service seemingly etched on his DNA.

He evolved in the long shadow of an extraordinary father, Nixon administration Treasury Secretary William E. Simon. A mercurial taskmaster, Simon Sr. demanded unswerving excellence from his eldest boy, who rarely veered off task.

Simon the son launched his campaign just six months after his father’s death, but friends and relatives say the bold bid for the state’s biggest job has less to do with paternal legacy than his own devotion to charity and his Catholic faith. He prays each morning and makes regular pilgrimages to Lourdes, the shrine at the foot of the Pyrenees. Over the last decade, as success in business left him feeling “strangely empty,” he has committed more and more time to good works--even hosting an inspirational cable show, “Sundays With Simon.”

“Bill could have lived the life of the preppy party boy, using his sinecure to run around and play golf and have a good time,” says John Morrissey, his neighbor in Pacific Palisades.

“But he’s a doer, and he’s tried hard to make something of the gifts he has. I honestly think he’s in this for the purest of reasons.”

Lattes on Doorsteps

A baby boomer with old-fashioned good manners and a self-deprecating wit, Simon is described by friends as a guy who’s never too busy to return a phone call--and likes to surprise neighbors by leaving morning lattes on their doorsteps.

Reared in New Jersey, he settled in California a dozen years ago and has adopted the Golden State lifestyle with gusto. He surfs with 12-year-old daughter Lindsay, hikes with wife Cindy in the Santa Monica Mountains and loves nothing better than a backyard barbecue.

Despite a personal fortune that could buy Brioni suits and dinners at Spago, Simon is a decidedly unflashy guy whose friends joke he’s never spent more than $5 on a haircut. He all but gave up drinking after a DUI conviction in his 20s, and now, at 50, his only apparent vice is a cheeseburger addiction.

“What’s that saying about the good example being the most irritating? Well, that’s Bill,” jokes Ted Knetzger, a boyhood friend.

Being the good example, however, has not always been easy.

Like others who are both namesakes and first-born sons of powerful men, Simon has borne the pressure of great expectations. One of his five sisters, Mary Streep, can still picture young Billy holed up in his room with a glass of iced tea, “studying, studying, studying,” while the rest of the brood played gin rummy or dominoes with Dad.

As a teenager, Simon was on the prep school honor roll and mastered German and Russian. At the same time, he was serving as captain of the tennis team, reciting the Mass in Latin and befriending poor kids as a Big Brother. Aside from a nasty temper on the court--his parents once took away his racket for a month--he was the kid who “always did the right thing,” recalls his younger brother Peter.

Simon’s drive and diligence are rooted partly in his father’s humble beginnings--and his promise that the sky was the limit for those who try hard. The senior Simon was a weak student in college, working at an ice house and changing truck tires when Billy was a young boy. But a chance meeting with a Wall Street executive abruptly opened a door, and the elder Simon pushed through it, launching his storied career in finance. Before long, the family had left their cramped basement apartment behind, ultimately settling in a three-story Tudor in Summit, N.J., when Billy was in fourth grade.

For years, however, his father kept the extent of his success a secret from the seven children--and from his wife, Carol. A former model who managed her bulging household with warm efficiency, she clipped coupons, knit radiator covers and allowed Billy a $20 tennis racket, not the $30 Davis Imperial he coveted.

The children learned the magnitude of their father’s wealth when he was tapped for the Treasury spot by President Nixon in 1973. Simon got the news from his college roommate, who came across a newspaper story pegging his father’s income at $3 million a year.

“We were all shocked, because we’d honestly had a pretty ordinary life,” Simon recalls. “We had a station wagon, I’d always had jobs--cutting lawns, working as a hospital orderly.”

The elder Simon--who went on to serve as Nixon’s energy czar and then amass a fortune through leveraged buyouts--died in 2000. But his imprint is visible on his son, sometimes painfully so.

On the campaign trail, Simon notes that his dad often derided him as “one of the great minds of the 13th century” when he did something dumb. He makes a joke of it, but Streep recalls that their father could “slice you in half with a single comment.” The parenting style, Peter Simon adds, was “not violent, but definitely forceful.”

Billy Simon left home for Williams College in 1969, a year of anti-war protests, sexual liberation and psychedelic drugs. It might have been a time for experimentation, for rebelling. It was not.

Instead, Simon was captain of the tennis and squash teams, got elected class president and hit the books--hard. “Bill didn’t grow his hair long or convert to Islam,” recalls Bill Eyre, a college friend. Vietnam loomed as a possibility, but the draft was canceled two weeks before his number was due to be called.

Simon had planned a career in medicine, but abandoned that idea after a string of Cs in science classes. Instead, he followed his father to Wall Street, sharing a brownstone in Greenwich Village with a bunch of pals.

Currency Trader, Enjoying Life

Working as a currency trader, Simon romped around the city with his twentysomething friends, enjoying what he has called “a wilderness period.” In 1978, he was stopped for drunk driving. Refusing a sobriety test, he was automatically convicted of a misdemeanor under New Jersey law.

Eventually, says his boyhood friend Knetzger, Simon “realized he had ceded a bit of control of his life to the fun elements associated with cocktails. He made a deep commitment to handle that, and he has been very successful.”

Simon calls the DUI a mistake of “youthful exuberance,” one he regrets and has never repeated. He drinks only rarely now because “as I got older, life picked up speed, and I didn’t have time for much of anything but work and family.”

Soon after the DUI, Simon met a bridesmaid at his brother’s wedding--Claudia Matthews--and married her. The couple moved to Boston, where Simon enrolled in law school, having revived an old dream of someday making a living in a courtroom. He got the law degree, but the marriage--while producing a daughter, Cary, now 20--didn’t take.

Simon calls the divorce, and eventual church annulment, perhaps the most painful time in his life. Aside from the obvious dilemma it posed for a strict Catholic, the split made the boy who never blundered feel as if he’d let everyone down.

“You feel awful, like you made a public mistake,” Simon says. He remains friends with his first wife and close to their daughter, but calls the split “just very, very sad” and “embarrassing.”

It was his mother who finally pulled Simon out of his gloom and onto a path that would define his adult life. She told him to volunteer at Covenant House, an organization that helps homeless kids, “where I’d meet some people who really had it tough.” He followed her advice.

“You’d get these kids right off the street, and we’d try to figure out their problems, how to help them. It was an incredible experience for me,” Simon recalls.

As his interest in charity grew, Simon’s professional life took another turn. After three years at a law firm, he signed on with the U.S. Attorney’s Office in New York, working under the man who would become that city’s world-famous mayor, Rudolph Giuliani. Like others in the office, Simon shouldered a mixed load, defending FBI agents while prosecuting drug dealers and chasing the assets of organized crime families.

Simon and Giuliani stayed in touch over the years, and their bond is proving fruitful. Giuliani appears in Simon’s campaign ads and has headlined lucrative fund-raisers on both coasts.

After three years as a government attorney, Simon veered back into the business world, joining his brother and father to create an investment firm. The transition was a bumpy one. The patriarch was endowed with a sizable ego and made clear where he stood in the pecking order. At the time, Simon told a friend he feared he “might just be serving coffee to Dad.”

But eventually, recalls sister Mary Streep, “Billy and Peter started standing up to him. They hashed it out, and they all started to bloom.”

Volunteered to Move West

When the trio decided to expand William E. Simon & Sons’ investments in the Pacific Rim, it was Bill Jr. who volunteered to move West in 1990 and open the firm’s Los Angeles office. Simon and his wife Cindy, whom he married in 1986, settled in Pacific Palisades, where they now live in a $3-million, seven-bedroom home with daughter Lindsay and sons William III, 14, and Griffin, 9.

With his investment business flourishing, but leaving him feeling unfulfilled, Simon began devoting more time to charity. The evolution was a natural one.

Simon’s parents had made it clear that “giving back was going to be part of who we were,” he said. To underscore his message, Simon’s father ordered his seven children to master Andrew Carnegie’s essay “The Gospel of Wealth,” which exhorts the moneyed to dispense their fortune “to produce the most beneficial result for the community.” In that regard, Simon’s greatest passion has been Covenant House.

Since moving west, he has served a term as its Los Angeles chairman, guided fund-raising campaigns and recruited other power players to the board. He also continues to spend hands-on time, says George Lozano, executive director of Covenant House California: “It’s not just about the board or writing checks for Bill.”

At Catholic Charities of Los Angeles, where he is vice chairman, Simon gets credit not just for improving fiscal accountability but for dropping in on programs in the field, making sure they deliver services as promised. And at Good Samaritan, a charity Simon launched with a friend, he screens grants to Southern Californians in distress.

Underpinning much of his philanthropy--and his everyday life--is Simon’s Catholic faith. Besides his frequent visits to Lourdes, where he helps the sick into its healing baths, he and his father once had a private audience with Pope John Paul II.

In a published essay, Simon said he has sensed through prayer that “God wanted me to preach.”

“There is serenity when one realizes that someone else is in charge,” he wrote, “especially when that someone is God.”

Those who know Simon confirm that he holds religious principles quite dear, but say he does not demand the same standard for those around him.

On the campaign trail, his faith comes up only when he outlines his position on abortion: “As a Catholic,” he says, “I am pro-life.” He typically adds that his wife is pro-choice, and that the law on abortion is settled, so “there’s not much a governor can do.”

The timing of Simon’s quest to become governor, coming just after his father’s death, has prompted some theorizing about whether he’s trying to outdo his famous dad. The candidate says there’s no connection. Rather, he feels that what he calls the “house of California” is crumbling. And he believes he can help.

Like many political greenhorns, however, Simon has found that campaigning is not as easy as it looks. He excels at working a room--exuding warmth and openness, finding a thread that connects him to whomever he’s wooing. But when it comes to debates or speeches before large groups, he is less natural, and displays a boyish enthusiasm that, in the cynical world of politics, tends to look contrived.

Simon has also struggled with another consequence of campaigning--the relentless media spotlight. Public attention is something he has vigilantly avoided in his business life. But now he’s a candidate, offering himself for inspection. And reporters want to tour his home, meet his kids and know his net worth, all requests he has denied.

“This is a very public thing--you’re out there tooting your own horn, and the attention is different for me,” Simon says.

More problematic, Simon is reluctant to put on the hard press when it comes to the lifeblood of politics--fund-raising. “I won’t risk losing a friend over it,” he says. So he trails former Los Angeles Mayor Richard Riordan in money raised, and by last month had been forced to loan his campaign $2.3 million--about half his total contributions.

He has also shown a distaste for attacking Riordan, the Republican front-runner and a friend who coaxed Simon into the race before deciding to join it himself. And he has found himself forced to explain his failure to vote in primaries in 1996, 1998 and 2000: He was tied up at work, he says, but admits “there’s no excuse.”

Political Newcomer, Economic Conservative

He may be new to the game, but Simon is well aware that his anonymity makes him a longshot. Still, he hopes his message as an economic conservative with a philanthropist’s heart will turn some heads.

Simon’s critics admit many of his ideas have merit. But they wonder why he’s starting at the top. Why not run, say, for attorney general, a job that meshes well with his experience as a prosecutor?

“What you have here is another example of the arrogant guy who thinks his wealth can buy the race,” says Sean Walsh, policy director for the other GOP contender, Secretary of State Bill Jones. “Maybe consultants filled his head with dreams of grandeur. But you’d think a guy with his background would have been able to resist the siren song.”

Simon says it’s fair to question whether his experience qualifies him for the job. Indeed, his life has been replete with skeptics questioning whether he won a job or honor the hard way, or merely by birthright.

That’s to be expected, Simon says. But he still bristles at those who “seem to be saying, ‘How dare you run?’

“Politicians don’t have a monopoly on leadership, and fortunately we live in a great country, where people can step up and say, ‘I don’t like what’s going on and I think I can make a difference.’

“If the voters say, ‘I don’t agree with you and I don’t want to give you a chance,’ then that’s fine. I’ve given it my best shot.”

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William E. Simon Jr.: His Life, His Words

* Born: June 20, 1951

* Residence: Pacific Palisades

* Education: Bachelor’s degree in history from Williams College, 1973. Law degree, Boston College, 1982.

* Party: Republican

* Career: Partner since 1988 in William E. Simon & Sons, an investment company launched with his father and brother. Previously was an assistant U.S. attorney in New York, prosecuting drug dealers and organized-crime families. Began career on Wall Street as a currency trader; practiced law for three years in New York. Vice chairman of Catholic Charities of Los Angeles, former chairman of Covenant House/California.

* Strategy: Persuading voters that a political rookie can use his experience in business and charity to be an effective leader in government.

* Personal: Married, wife Cindy. Four children, one with his former wife, Claudia Matthews.

*

‘Politicians don’t have a monopoly on leadership, and fortunately we live in a great country, where people can step up and say, ‘ “I don’t like what’s going on and I think I can make a difference.”

‘This is a very public thing--you’re out there tooting your own horn, and the attention is different for me.’