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Friday, Feb. 29, 2008 | When Republican prosecutor Bill Gentry suddenly dropped out of the San Diego city attorney’s race last month, Judge Jan Goldsmith was sitting pretty. As the lone Republican in the race, with the endorsement of the local Republican Party, Goldsmith looked like he had a sizable chunk of the vote tied up.

But any hopes Goldsmith may have had of turning the race into a one-on-one partisan match-up between him and Democratic incumbent Mike Aguirre soon evaporated. A few days after Gentry’s departure, City Councilman Brian Maienschein shocked Goldsmith, and most City Hall observers, by running for Aguirre’s seat. Soon after, Council President Scott Peters decided he would have a crack at winning the job too.

Goldsmith now finds himself in a well-populated political donnybrook. And, while it seems like he genuinely wants the job, he doesn’t appear too excited about the campaign ahead of him.

He’s facing two well-funded and experienced local politicians, an incumbent with a solid fan base and two ambitious local Democratic attorneys. And the race ahead of him will, by necessity, involve a huge amount of fundraising, an element of the political process he has said he dislikes.

By the end of last year, Goldsmith had raised a little more than $8,000, and he has strictly ruled out spending any of his own money on the campaign. Both Peters and Aguirre have the means to self-finance their campaigns. Overall, Goldsmith gives the impression the election race has morphed into exactly the sort of potentially scrappy political undertaking that led him away from politics and onto the bench almost a decade ago.

“I said I don’t want any more politics. The good stuff is important, but the hardball stuff like money-raising isn’t,” he said. “The more I got to know it, the more I realized I didn’t like it.”

But, like it or not, Goldsmith walked into a race that has messy politics written all over it.

Even without Peters and Maienschein in the race, Goldsmith would still have had to face Aguirre, probably the most divisive political figure in the county. Now, he has to fight tooth-and-nail, campaigning hard towards a primary election on June 3. If no candidate wins 50 percent of the votes that election, the top two vote winners get back on the campaign trail for another six months of campaigning and fundraising before a final vote which is held on the same day as the presidential election in November.

The appearance of Maienschein in the race is particularly galling for Goldsmith and his Republican supporters.

As a conservative Republican, Maienschein will be competing directly with Goldsmith for approval from a crucial voting bloc. In his seven years on the City Council, Maienschein has built up a solid base of support along northern San Diego’s conservative “I-15 Corridor” communities of Rancho Bernardo and Scripps Ranch. That area was once the heart of Goldsmith’s political support when he was a city councilman and mayor of Poway in the 1980s and served in the state Legislature in the 1990s. Maienschein also has a healthy campaign war chest of more than $250,000 he raised in his uncontested run for reelection to the City Council in 2004.

Larry Remer, a local Democratic political consultant not involved in the city attorney’s race, said Goldsmith’s aversion to fundraising could be more of a reaction to the situation he’s been placed in than a character trait he has had for a long time. Goldsmith has run for office before and he knows the rules of the game, Remer said, so he should have been expecting some tough months of fundraising.

“He’s not a babe in the woods,” Remer said. “This is either buyer’s remorse or a political miscalculation if he’s decided that just because a group of fat cats wants to fund him the waters will part for him.”

But Republican political consultant Duane Dichiara said Goldsmith’s fought some brutal campaigns in his time. He said the campaigns Goldsmith ran in the 1990s to keep his seat in the state Legislature were certainly not walkovers, and that the judge’s dislike of fundraising is completely natural, if not laudable.

“Very few people like running for office,” Dichiara said. “I can’t think of any of my clients that actually liked running for office, between the attack ads and raising the money. And I don’t know if our first pick should be someone who actually likes that stuff.”

But at least one of Goldsmith’s competitors says he relishes it. At Maienschein’s press conference Thursday to announce his run for city attorney, he addressed the crowd:

“I’m excited to get out there and campaign. It’s something that I enjoy doing, believe it or not, so I’m looking forward to the campaign.”

At Maienschein’s side will be the $250,000 war chest he raised in 2004.

Goldsmith has argued that Maienschein shouldn’t be allowed to roll his funds, from his successful City Council campaign, over into his city attorney campaign. He has complained to the city’s Ethics Commission to that effect and said he realizes fundraising will be a crucial component of the city attorney’s race but hopes he can overcome his obvious disadvantage.

“If this is all about money, there’s no way I’m making it, but I’m betting it’s about more than that,” Goldsmith said.

Goldsmith has his own support in the form of the Republican Party, which can raise large amounts of money to communicate with Republican voters. He has also hired an experienced local fundraiser, Jean Freelove.

But Goldsmith said he’s spent the last nine years on the bench where, “you don’t ask people for money.” He said he will certainly not commit any of his own money to the race and pointed out that he’s already forgoing his $175,000-a-year judge’s salary to make the commitment to run.

But though he’s not a fan of the journey he will have to take to the City Attorney’s Office, Goldsmith said there’s no doubt he wants the job.

He talked animatedly about his days as a politician in Poway and his years as a legislator in Sacramento. He said he’s proud of his work as a small town mayor and of the laws he helped to create during the 1990s. He said he enjoyed everything about public office apart from being so far away from his family.

“In the middle of Poway, there’s a plaque with my name on it,” he said.

But Goldsmith admitted that he’s out of practice when it comes to politics. Before he decided to run, he said, he told Republican operatives that had asked him to consider the race that he had some serious doubts about leaving his position as a judge.

“I said ‘I’m not sure I have it in me to do the politics,’” he said.

Local political consultants not involved in the city attorney’s race said the fact that Goldsmith has been out of the public eye for almost a decade clearly makes a big difference in terms of his recognition factor with the public. But Dichiara, the Republican consultant, said just because Goldsmith doesn’t like to play the politician doesn’t mean he can’t do it. Dichiara said he has no doubt Goldsmith will grin and bear it when it in the coming months and will call on his experience as a politician, however long it has been since he was in the public eye.

“I would say it’s like riding a bicycle. Once you learn how to ride, you can go off to the Himalayas, where you’re not going to be riding a bicycle, for 10 years. But when you come back, you’ll still be able to ride pretty well,” he said.

Please contact Will Carless directly with your thoughts, ideas, personal stories or tips. Or send a letter to the editor.

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