When the mayoral election is over in November 2012, San Diego could have its first openly gay elected mayor, first Democratic mayor in two decades or continue its long line of coastal Republican leaders.

The high-profile free-for-all that’s the San Diego 2012 mayoral election begins in less than a week with the start of official fundraising. Already, it’s attracted Republican and Democratic star power from city, county, state and federal elected offices. It’s the rare election with no incumbent or obvious successor, and it comes with greater powers to set the direction of the nation’s largest cities.

“You have a whole steaming pot of political adversaries,” said Richard Ledford, a longtime local Republican lobbyist.

A mayoral campaign could cost as much as $1 million through next June’s primary, political strategists and other observers said, and prospective candidates have a brief window this month to show their strength and viability to donors.

Campaigns have from the election’s official start on June 5 to the end of the month to raise money before the next financial reporting period ends. The money that candidates can raise in June will be the only public disclosure of their finances until the end of the year.

Do well and more donors and endorsements could follow. Do poorly and donors and endorsers might go somewhere else.

“You have 24 days in June to make a statement,” said Tom Shepard, a longtime political strategist who’s working for state Assemblyman Nathan Fletcher’s campaign.

This month, the half dozen or so major candidates expected to declare will try to sell their strengths to donors and downplay their weaknesses. Here’s a quick, early analysis of six major candidates who already have or could enter the race.

Carl DeMaio, Republican, City Councilman

DeMaio has filed his papers to run, but has yet to fully commit. (A campaign spokesman said he expects to make an announcement in the next week or so.) No other candidate will attract as much attention as him. He’s a master of sound bites and self-promotion. He’s laid claim to the fiscal reform mantle, which could once again be the campaign’s key issue. He co-authored a ballot measure to replace pensions with 401(k)-style retirements for most new city employees and developed his own comprehensive budget plan. He’s also expected to fundraise well.

The key question facing DeMaio is if his popularity has a ceiling — can an anti-establishment candidate get more than 50 percent of the vote in San Diego? Organized labor essentially has declared open war against him (there’s an @AnyoneButCarl Twitter handle) and he doesn’t have a lot of friends among the downtown establishment.

Bonnie Dumanis, Republican, District Attorney

So far, Dumanis is the only candidate both to officially declare for the race and say she’s in for the duration. We’ve dubbed Dumanis the Most Powerful Politician in San Diego. She’s an ally of Mayor Jerry Sanders and was considered a shoe-in for his endorsement until she opposed Sanders’ current signature financial reform: the 401(k) ballot measure. Dumanis believes the measure goes too far, but hasn’t yet developed her own plan to address the city’s fiscal problems.

That could point to her biggest weakness. She hasn’t yet demonstrated an ability to engage with city issues, financial and otherwise, and often is criticized for playing too close to the vest.

Still, her advantages are enormous. As district attorney, she has tremendous name recognition, has won countywide elections and managed a big bureaucracy. She is well-liked among the downtown establishment and in the gay community and should have no problem fundraising. Her campaign expects to hold as many as a dozen events in June.

Kevin Faulconer, Republican, City Councilman

During his more than five years on City Council, Faulconer has championed Republican causes such as a ballot measure for competitively bidding city services, opposing a sales tax increase and signing onto the 401(k) measure. He’s also a big backer of building landmark projects downtown. He’s also distinguished himself from DeMaio by being the crucial swing vote on a deal to cut retiree health care benefits for current employees.

But it’s hard to see where Faulconer fits. Dumanis is in the race and though Fletcher hasn’t officially declared, he’s almost there. All three will be fighting for the moderate Republican space occupied right now by Sanders. Should Faulconer declare, fundraising figures will be big for him as well. He has a boost: $75,000 left over from his City Council campaigns.

Bob Filner, Democrat, U.S. Congressman

Filner knows the city, is a veteran of tough campaigns and is known for hard work. His chief strengths are his experience — he’s served on San Diego’s City Council and the school board — and his proven ability to fundraise. Filner’s 18 years in Congress have given him a national profile and he’s well known for his work promoting veterans. That’s not a bad cause to have championed in a military town.

It’s unclear, though, how much attention he’s been paying to city issues while he’s been in Congress. He’ll have to develop his own financial plan and vision for the city. And his cantankerous reputation could cut both ways.

Nathan Fletcher, Republican, State Assemblyman

Fletcher, who hasn’t officially declared, is probably the candidate most likely to soar or flop. It’s difficult as a Republican in the state Legislature actually to pass new laws. Fletcher has. He sponsored Chelsea’s Law, which put greater restrictions on sex offenders in the wake of last year’s murder of Poway teenager Chelsea King. Fletcher also was the driving force behind the controversial late-night legislation to lift a key limit on downtown redevelopment.

The resulting storm that came after the redevelopment deal highlighted Fletcher’s inexperience, which could be his biggest weakness. He hasn’t been in a major competitive race before. But even though he’s inexperienced, he’s lined up people who know the city. Shepard is the mayor’s consultant and considered one of the best in town. Fletcher’s new chief of staff is a veteran of the Sanders’ administration. And Fletcher, an Iraq war veteran, is said to be the favored candidate of former Mayor and Governor Pete Wilson and his team.

As a moderate and relative unknown, the June fundraising figures matter as much for Fletcher as anyone. Shepard said the campaign hopes to raise $100,000 by the end of the month.

Christine Kehoe, Democrat, State Senator

Like Filner, Kehoe is a longtime legislator. Her experience has earned her friends in the environmental and gay communities. She was the city’s first openly gay elected official and helped start revitalization efforts in City Heights, one of San Diego’s most underdeveloped neighborhoods.

But her experience also has downsides. She’ll have to answer to her vote in favor of the city’s first pension underfunding plan in 1996, which began digging a hole out of which the city has yet to emerge. Her answers on pensions and finances will be even more significant because of her history.

Please contact Liam Dillon directly at liam.dillon@voiceofsandiego.org or 619.550.5663 and follow him on Twitter: twitter.com/dillonliam.

Liam Dillon

Liam Dillon was formerly a senior reporter and assistant editor for Voice of San Diego. He led VOSD’s investigations and wrote about how regular people...

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