In what has become one of the most closely watched and hotly debated election battles in recent San Diego history, incumbent City Attorney Mike Aguirre has found himself fighting for his political life against four opponents, including two sitting city councilmen and a retired judge.

The position of city attorney of San Diego, once considered a benign, even boring legal advisory role, has morphed into one of the most powerful and sought-after positions in city government.

That’s largely Aguirre’s doing. Since his election in 2004, the incumbent has redefined the scope and impact of the City Attorney’s Office. By asserting that the city attorney is accountable to the people of San Diego directly, rather than via the authority of the City Council, Aguirre has effectively placed the office, and himself, at the forefront of policy and politics at city hall.

Consequently, Aguirre has spent the four years since his election issuing legal decisions, holding press conferences, completing investigative reports and generally asserting his authority as a “voice of the people” like no other city attorney for at least the past 50 years.

Pat Shea, a one-time candidate for San Diego mayor and a close friend and adviser to Aguirre, described the sea change at the City Attorney’s Office using an analogy:

“In a sense, it’s like a chess board,” Shea said. “Forever, a political player in San Diego would look at the City Attorney’s Office and say ‘That’s a pawn.’ Mike came out and said, ‘Really, this is like a bishop, or even a queen. It can move in a lot of different directions, and if I don’t act like a pawn, but act like a queen, then I jump to whatever issue I choose to.’ It’s a very powerful piece on the board and he made it that way.”

Two sitting city councilmen, Brian Maienschein and Scott Peters both decided to challenge Aguirre earlier this year. Both announcements were unexpected, but Maienschein’s was a bombshell to local Republicans.

Maienschein, himself a conservative Republican, seriously rocked the local Republican party when he threw his hat into the race. Local Republicans, after some initial faltering, had already endorsed conservative Judge Jan Goldsmith, a former state legislator and mayor of Poway as their chosen candidate. They voiced concern that Maienschein could split the Republican vote and hamper their candidate’s chances.

Joining Peters, Maienschein, Goldsmith and Aguirre in the race is local democratic attorney Amy Lepine, who one worked for Aguirre and is currently suing him and the city for sexual harassment and wrongful termination. Considered the underdog in the race, Lepine has nevertheless injected a feistiness into recent candidates’ forums that other contenders have avoided, and has been taking the race extremely seriously.

The candidates face off against each other in a primary election on June 3. If none of the candidates wins 50 percent of the votes, the top two vote winners proceed to a runoff election to be held on the same day as the Presidential election in November.

Recent non-partisan polling suggests Aguirre will make it into a runoff. All eyes, therefore, are on second place.

Until March, Maienschein bested the other candidates in fundraising, building on a campaign war chest of more than $250,000 he amassed during his uncontested run for reelection to the city council in 2000.

But by mid-May, Scott Peters was pulling in more money in individual contributions than his opponents. Maienschein had spent much of his war chest and Aguirre and Goldsmith were both out-fundraising him.

Scott Peters also has his own money to spend and has been pumping cash into advertising. He has played on his 15 years of experience as an environmental lawyer, some of which were spent as a county counsel, as evidence that he’s the most accomplished attorney to take over from Aguirre.

And Goldsmith, with the financial backing of the Republican Party and endorsements from Republican heavy hitters District Attorney Bonnie Dumanis and Sheriff Bill Kolender, and an extensive legal and political career, has been polling well and appears to appeal to many conservative voters.

The two councilmen must overcome their association with the city’s pension scandal, an issue that has overshadowed the race and has dominated many of the city attorney debates in recent weeks. Goldsmith will have to resurrect a political career that’s been dormant for almost a decade. Aguirre will have to convince voters that his reign has been more about real impact than frivolity and Lepine will have to continue the battle to make her name stand out against the well-known and experienced group running against her.

Right now, it’s anybody’s race.

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