Behind That Winning Smile, a Bulldog Spirit

When Bill Simon Jr. told his eldest sister he was running for governor last year, she gave him some free advice: “You’re crazy!” How, she wondered, could her gentle, lighthearted brother survive in the “snake pit of politics?”

The snakes may eventually get Simon, but he got through Round 1 in the pit without losing much blood. In a wild finish that astonished even the most seasoned political pros, the Los Angeles investor knocked off the GOP gubernatorial favorite--Richard Riordan--with ample votes to spare.

Now comes eight months of war with Gov. Gray Davis. And as a hoarse but gleeful Simon reveled in his newfound status Wednesday, a few fateful questions hung in the air:

Just who is this mega-rich, 50-year-old father of four with the Clark Kent look and perpetual smile? And does he have what it takes to stand up to Davis’ withering attacks?

On the surface, there seems reason to wonder. Aside from a turn as class president at Williams College, Simon is an utter political greenhorn. A New Jersey transplant who settled here 12 years ago, he hadn’t even visited much of California until the campaign trail led him there.

And though Simon never wavered in his yearlong drive to win the state’s top political job, he admitted Wednesday that the reality of his improbable coup is somewhat hard to fathom:

“This is a little bit overwhelming for me,” he told a cheering breakfast crowd in Los Angeles. No doubt. Just moments before, President Bush had called to congratulate him on the double-digit win--and offer whatever help he might need.

While comfortable in the spotlight, it is not a place where Simon--a self-deprecating sort--typically resides. Despite his personal fortune--he won’t reveal his exact net worth--he is not one to rub elbows with bigwigs and eschews many of the trappings of wealth.

He may live in a $3-million home in Pacific Palisades, but friends say he’s happiest in a sweatsuit shooting hoops or eating a hot dog on the beach. Until recently, he drove an old powder-blue Cadillac that often had his surfboard strapped on top.

A father of four, Simon the candidate still tries to get home at night to help out with homework. Campaign schedulers, meanwhile, are under orders to work around his daughter’s horse shows and overnights with his son’s Boy Scout troop.

Active in a host of charities, Simon is also a devout Catholic who has made numerous pilgrimages to Lourdes, the shrine at the foot of the Pyrenees. He says he tries to live by his mother’s admonition: “Character,” she told Bill and his six younger siblings, “is what you do when people aren’t looking.”

Pundits marvel at Simon’s surge from obscurity, but friends of the earnest guy they call Billy say they never counted him out. A former federal prosecutor in New York, Simon has a sunny exterior that masks an indefatigable drive.

“He’s an unbelievable plugger,” says friend Barbara Lyne. “He’s like the dog on your leg,” adds Henry Brandon, who works at Simon’s West L.A. investment company, William E. Simon & Sons. “You keep shaking and shaking and he’s always there.”

Tenacity is clearly an asset in politics, but Simon would probably not be where he is today if not for one thing--his wealth. It took $5 million of his own money, plus about half a million from siblings, to help finance his primary campaign.

That said, Simon’s family pedigree makes government service a natural. His late father, William E. Simon, served as Treasury secretary to presidents Nixon and Ford and as Energy secretary during the oil crisis of the early 1970s.

Until last year, however, Simon the son had charted a different course, preferring to focus his public life on charity work. Most of his time and money have been spent on Covenant House, which provides shelter and other help to runaway teens, and Catholic Charities of Los Angeles. He and his wife, Cindy, also launched a foundation that funds scholarships and school improvement projects.

Simon portrays his foray into politics as an extension of his philanthropic work, but it also reflects his deep faith. In recent years, his business accomplishments have left him feeling “strangely empty.” Becoming governor, he figures, is another way he might serve God and play a more meaningful role.

As it is for many rookies, the transition from private businessman to candidate was a rocky one for Simon. Despite a battery of consultants and public speaking tips from his priest at St. Monica’s Catholic Church, he appeared wooden and overly scripted in his early campaign speeches. He struggled to master the myriad issues confronting the state, and faced tough questions about his spotty voting record and credentials to vault from nowhere to governor.

“There were definitely good days and days that weren’t so good,” said John Herrington, his campaign chairman. “He wasn’t used to the exposure.”

In recent weeks, however, Simon’s performances took a dramatic turn, showing new polish, greater command of policy and comfort before the cameras.

He was buoyed in part by campaign help from his old boss at the U.S. attorney’s office, the popular ex-mayor of New York, Rudy Giuliani. Joining Simon for fund-raisers and in TV ads, Giuliani provided a validating presence that analysts say helped put Simon on the map.

Scattered around Los Angeles, Simon’s friends had only one lament as they watched their buddy become the GOP nominee:

The popular pickup basketball game he used to host at his home each Friday afternoon will be suspended for another eight months. Or more.

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Times staff writer Nicholas Riccardi contributed to this report.