She tells Fortune that she might spend $50 million of her own money on the campaign. That figure daunts even Jerry Brown, the state attorney general who's running for a second stint as governor: "That's a lot!"

But what does she bring besides money? The article glosses over her spotty voting record — she voted in less than half of the past 10 year's elections. And it also gives her a pass on her opposition to gay marriage. That position, in particular, has enraged natural supporters inside eBay and around the Bay Area, where a business conservative might otherwise hope to win crossover votes. (Puzzle this one out: Whitman's longtime assistant at eBay, Anita Gaeta, is a lesbian who lives with her partner in San Jose, and is working with her on the campaign.)

Whitman's fundamental mistake seems to be thinking that the decisiveness she displayed as eBay's CEO will translate into governance. Hold on a second. Was Whitman that great a CEO, beyond eBay's first few years, when the startup was fueled by the strength of founder Pierre Omidyar's idea of an online auction?

She made several bad mistakes in the second half of her career at eBay: buying the voice-over-Internet startup Skype for $2.6 billion; enraging eBay's sellers by hiking fees; and putting a revolving door of leaders through PayPal, the company's online service, which eBay is only now focusing on as a growth engine.

So, let's review: This is a person who engaged in wasteful spending, raised eBay's equivalent of taxes, and squandered opportunities for growth.

"Being CEO of the state is not a popularity contest," she says. Well, actually, last time we checked, getting the job was. Whitman had better start trying being popular, because running on her business record seems like a non-starter.

Newsom, a Democrat, has declared himself a candidate for California's governor seat, a wide-open race taking place next year, since term limits are keeping Arnold Schwarzenegger from running again. A rising star in the Democratic party, Newsom has hurt himself with gaffes both personal and political.

He and his first wife, Fox News TV host kimberly Guilfoyle, divorced in 2006. While going through the divorce, Newsom had an affair with Ruby Rippey-Tourk, the wife of his campaign manager, Alex Tourk. The divorce and affair ruined Newsom's Camelot-by-the-Bay image.

His wedding last year to Siebel, a cousin of wealthy software entrepreneur Tom Siebel, was a step towards restoring his tattered image. (Google founders Larry Page and Sergey Brin ferried guests in their private jet to the wedding site on a Montana ranch.)

But then came Proposition 8, California's ban on gay marriage, a cause Newsom has championed since he defied state law in 2004 by issuing marriage licenses to gay couples (including the author of this post). At a rally, Newsom declared that gay marriage was coming to California "whether you like it or not," a sound bite Prop 8 supporters aired endlessly in TV commercials and was cited in many election post-mortems as a factor in the passage of Prop 8.

With memories of his messy personal life still fresh, and his main cause defeated in the last state election, Newsom's push for the governor's seat looked like it was off to a rocky start. In the Democratic primary, he faces California Attorney General Jerry Brown, the former Governor Moonbeam.

But political observers say Brown may strike potential voters as too old. With Newsom's wife expecting a child in the fall, he will have the perfect family-man campaign prop. What better way for a claimant to the throne to seem young and vital than to have his very own heir?

Update: The mayor's office has confirmed that the Newsoms are expecting. Spokesman Nathan Ballard said:

We are pleased to confirm that Mayor Gavin Newsom and First Lady Jennifer Siebel Newsom are starting a family. The Mayor and the First Lady are thrilled to be embarking on this adventure together, and they appreciate your good wishes.

Guess who wasn't expecting this? Gavin's dad and Jennifer's mom, both of whom told the San Francisco Examiner that their children hadn't let them in on the secret.

(Photos by Getty Images)

Agencies and advertisers are bit players in this. Microsoft has been lobbying reporters to write about this stuff. They have a huge lobbying apparatus in place from the antitrust battles of the '90s. Some very high up people at [media] holding companies don't even think it's worth their time to get involved because it's a lobbying battle. And for agencies, they know they're being used, but they think Google need to get its snout hit.

(Photo by AP/Sarbach)

Dear Attorney General Brown:

I am writing to urge you to direct your office to take quick and decisive action by launching a formal investigation into the proposed business transaction between Google and Yahoo's search advertising business which would give Google control of 90+% of the search advertising market, making its already dominant position even stronger. Aside from the competitive issues this proposed deal raises, it also highlights the market power that would be concentrated within Google. This power would allow the search giant to unilaterally develop “online privacy policies” related to search and other forms of online advertising. Currently, Google is not entirely transparent about the type of personal data it collects (i.e. search terms, YouTube viewing habits, web browsing habits), how long they keep it, how they “data mine” it across their properties, and how exactly they use the information.

Recently, I worked together with privacy organizations and successfully forced Google to reverse its position – in compliance with the California Privacy Protection Act – and link to its privacy policy prominently from its homepage. The struggle to achieve what should have been a simple victory indicates that Google does not value online privacy concerns as much as it purports.

At both the federal and state levels, a bi-partisan collection of elected officials and regulators are conducting comprehensive investigations into this proposed business transaction. Most notably, the U.S. Department of Justice has launched an anti-trust investigation that appears wide-ranging based on media reports of subpoenas and other developments. In Congress, both the Senate Commerce and Senate Judiciary Committees have held hearings in the past week, as well as the House Judiciary Committee. Leading privacy advocates like Republican Congressman Joe Barton (TX) and Democrat Senator Herb Kohl (WI) are aggressively questioning the impact of this business deal on consumers, advertisers and the e-commerce marketplace.

At his Subcommittee's hearing on Tuesday Chairman Kohl expressed concerns that this deal “will reduce Yahoo to nothing more than the latest satellite in the Google orbit.” Senator Kohl has promised to thoroughly investigate the “privacy implications of this deal.”

Your colleagues in other states are also scrutinizing this deal, including Connecticut Attorney General Richard Blumenthal and Florida Attorney General Bill McCollum. Blumenthal stated “on their face, those numbers cry out for an inquiry. If their agreement is a substantial one in its impact on services or costs, it could have a huge impact on competition. It could be hugely anti-competitive.”

The impact of such potential market concentration – in both internet search and search advertising – left in the hands of one company, at the very least, warrants rigorous scrutiny. We must ensure that the proper consumer safeguards and transparency are put in place to protect privacy. The ability to “data mine” online behavior in order to find specific consumers interested in specific products is a big part of Google's revenue stream and business plan. If Google is allowed to control over 90% of Internet searches, those data mining capabilities will be unmatched and will soon make it impossible for any competitor to crack Google’s stranglehold on web advertising.

We look forward to your prompt response.

Respectfully,

Joel Anderson
California State Assemblyman

Yes, Jennifer is one of those Siebels — her dad, Ken Siebel, is a cousin of Tom Siebel, the founder of Siebel Systems. The father of the bride is also chairman of Private Wealth Partners, which manages a $444 million fund. But Newsom might find it difficult to pry any campaign contributions from his new father-in-law, since the elder Siebel has donated only to Republicans in national elections since 2000, including George W. Bush, John McCain and Rudy Giuliani.

Newsom did at least convince the bride's family to host the wedding in Stevensville, Montana, where the groom wore a casual linen suit and the bride wore Vera Wang and rode down the aisle bareback on a white black stallion. By far the best blow-by-blow of the nuptials was from Newsom's predecessor at City Hall, Willie Brown. Siebel and Newsom plan to tour Africa on their honeymoon — no word if they intend to indulge in the hot celebrity trend of adopting a child as a souvenir.

Being in the family way might help burnish Newsom's image after an adultery scandal in 2007 and a public admission of the entrepreneurial wine salesman's drinking problem. The timing of this marriage eerily reflects that of Newsom's first in 2001, when the then-Supervisor wed Kimberly Guilfoyle months before he announced his candidacy for mayor of San Francisco.

But the couple divorced a year after he was elected amidst talk of a new "Camelot" couple rising in the Democratic Party ranks. You can expect the eternal flame of the media's love for Newsom to be rekindled along those lines, though I doubt the newlyweds will be posing in any oil-money mansions this time around.

With Newsom now fielding an exploratory committee to run for statewide office, longtime superfan and San Francisco Chronicle blogger Beth Spotswood was generous: "I give them two years, that's my wedding gift to Gavin." Which is just long enough to last until June 8, 2010, when the votes for Governor will be tallied.

Hopefully Siebel can continue to steer clear of commenting on blogs in the meantime. Siebel's first publicity challenge will be to show up California attorney general Jerry Brown's longtime partner and current wife Anne Gust in the primary, followed by Maria Shriver, wife of California Governor Arnold Schwarzenegger. (Photo by Getty Images/Meg Smith)

Any California customer of the five ISPs already signed on in New York is included in the restrictions. For customers, the initiative's inability to target porn-serving newsgroups means the loss of access to many innocent newsgroups. But there are countless workarounds for Usenet users, a demographic dominated by technical types, to get access. For Cuomo et al., the initiative sounds so good on paper that they don't have to even bother making it work.

Speaking of which, the crowd included Chuck Phillips, the president of Oracle; Accel Partners' Jim Breyer; Google angel investor Ram Shiram; Gavin Newsom; former California governor Jerry Brown; Jessica Guynn of the Los Angeles TimesBarron's; AllThingsD's Kara Swisher; former Chronicle editor Phil Bronstein; MarketWatch's Therese Poletti; Craig Newmark; and renowned San Francisco socialite Denise Hale, who rather liked my tie.

Zittrain's book is about the tradeoffs between freedom and control, security and creativity. New devices like the iPhone provide a safer, smoother experience than the uncontrolled Web — but at the cost of having a gatekeeper, Apple, dictating what can and can't run on the device. That kind of chokepoint, in turn, makes it far easier for government regulators to get involved. The alternative, though, is not particularly attractive: an Internet ruled by spammers and hackers.

Like his counterparts in politics, Zittrain is seeking a third way. I couldn't help but think this impulse is driven by an early experience he related at the party: Getting beaten up in high school. (He thanked the hostess, Melanie, "for not beating up on me.") Having been bullied, Zittrain doesn't want revenge: He just doesn't want anyone to bully, or be bullied. This moderating impulse is seen in a passage where he discusses how neither governments nor citizens ought to be able to wholly circumvent the law through technology:

Perhaps it is best to say that neither the governor nor the governed should be able to monopolize technological tricks. We are better off without flat-out trumps that make the world the way either regulator or target wants it to be without the need for the expenditure of some effort and
cooperation from others to make it so.

And yet Zittrain's career could well exceed Lessig's. That he was able to fill a room — an impeccably furnished, tastefully modern room in one of San Francisco's wealthiest enclaves, at that — speaks to his draw. Liberal San Francisco politicans, self-made entrepreneurs, and the Web's wacky fringe can all find things they agree on in his work.

The danger for Zittrain is that his work might be nothing more than a justification for compromise and tradeoffs. Will he find a third way for the Web — or just point out the middle of the road? His calls for a "generosity of spirit" are reminiscent of the assumptions that turned eBay, a marketplace of strangers, into a very profitable community of traders. Hoping for the best really can pan out, as it happens. But the answers Zittrain will have to find, or inspire, are far more complicated than asking someone to be on their best behavior.