Westly

Two weeks ago, the Weekly’s cadre of political experts ID’d Steve Westly as Arnold Schwarzenegger’s toughest Democratic opponent come 2006. Since then, Westly has treated the news like peanut butter — spreading it on every available surface. Okay, we can suspend reality with the best of them, so what about the guy?

Uber-ambition is to a politician what wizardry is to Harry Potter–it defines your essence and, as an asset, is probably more important than being glib in front of 6 million viewers. That’s why it is significant to remember that Westly ramped up at an early age. He was only 23 when he became treasurer of the California Democratic Party and barely 32 when, in 1989, he very nearly, almost, just about, but not quite, became chairman.

Westly spent the better part of ’89 hustling the chairmanship, nailing down support in advance of the party’s convention in Sacramento. What he could not anticipate was the similarly intense if chaotically applied ambition of another, slightly better known California Democrat–Jerry Brown, who emerged from the wilderness to re-ignite his political career with the same job. In the flicker of a moment, Brown consigned Westly to the outer fringe of relevance.

How a tyro handles disappointment can speak volumes about his tenacity.

Fast-forward to 1997 where Westly, by then a techie business dude and Stanford lecturer, stepped onto the ground floor of a rocket-powered elevator known as eBay — the 23rd employee of a dot-com enterprise about to experience the kind of explosive success that turns option-saturated employees into facsimiles of Warren Buffet. Within a few years, Westly was among those Silicon Valley red-hots who redefined affluence, having amassed more than $100 million in personal wealth. By 2002 he was primed to reassemble the fragments of his political ambitions, and his path to fulfillment was state controller. To seed his campaign, Westly wrote himself a check for $1.6 million.

From the get-go, Westly sought the job as though it was posted on eBay–he bid high and bid often, eventually spending at least $5 million of his own money. He used some of it to bury Democratic primary opponent Johan Klehs, who had a long elective career, but no cash. He used even more of it to squeak past Republican Tom McClintock in the general election, winning by fewer than 20,000 votes.

Once in office, Westly careened through his first two years the way an impulsive teen-ager might teach himself to drive–sometimes on the left side of the road, sometimes on the right, with a few dents and broken headlights along the way. He also revealed a sense of opportunism, which often combines with ambition to form a political fuel not unlike hydrogen–combustible, unstable and highly unpredictable. The formula can whip you into hyperdrive, but then, there is the Hindenburg to consider.

Westly showcased all of this in 2004 when he co-chaired Schwarzenegger’s campaign to pass Props. 57 and 58–measures meant to address the state’s fiscal woes through borrowing and a spending cap. The governor was at the crest of his popularity, and Westly conspicuously glued himself to the campaign, injecting it with a bipartisan flavor. He also went out of his way to distinguish himself from gubernatorial rival Phil Angelides, the Democratic state treasurer irked these days because voters can’t tell Democrats from Republicans.

The propositions were approved, but the victory party provided a photo op that could haunt Westly the way “Jersey Girl” and “Man About Town” dog Ben Affleck.

Westly and the governor are celebrating together. But while Arnold beams his Ipana smile, Westly looks as though he just graduated from the Howard Dean Academy of Political Screams.

In a general election, that photo could suggest Westly as an enthusiastic problem-solver able to work with all comers to unravel the state’s various Gordian knots. But before the controller can promote an impression of himself, he must first survive the party primary where Angelides, his brass knuckles newly polished, likely will fire-hose a different twist into Democratic mailboxes everywhere: Steve Westly, the Schwarzenegger lapdog.

At 47, Westly is still young for a politician with grand designs, and he has the luxury of time. Let’s see if he can balance ambition with patience and use sound political judgment when charging at windmills.