Thursday, Sept. 4, 2008 | Labor Day is behind us. That means it’s election season. We could talk about a lot of things, but let’s go with the sexiest — the most interesting and consequential local race: The campaign for San Diego city attorney.

Few things could affect our city as much who its top lawyer is. This would sound pretty strange to a new arrival to the city’s political scene, but it’s a given fact to the rest of us.

The following is a list of the five things you should look for in the following nine weeks. The outcome of each will shape San Diego indefinitely.

1) How much money does the incumbent have, or better, how much will he spend?

City Attorney Mike Aguirre financed most of his successful 2004 campaign with his own personal wealth.

But for this year’s June primary, he simply did not run a campaign of any mention. He made the calculation that — with no less than four competent challengers — he would probably not win enough support to avoid this upcoming general election. But, he rightly determined, he had a base of support that would ensure that without much effort, he would advance to the final election.

So why try at all? It was pretty shrewd, actually. He weighed the cost of what underperforming in the primary did to his public image against the benefit of saving all of his money for what he deemed an inevitable final race. He thought he’d be facing Council President Scott Peters and aimed most of his invective at that long-time rival. But Judge Jan Goldsmith made a strong showing instead, vacuuming up the vote of those who wanted a new city attorney but couldn’t stomach Peters or his council colleague, Brian Maienschein.

Now, we have to wait and see how much money Aguirre saved and how much he deploys now. I’m not privy to any polling at all but, after the primary, Goldsmith’s got to be the frontrunner right now. Aguirre’s going to need a well-organized, strong and well-funded re-election campaign. He’s not raising much money. If he decides not to spend money — or not to spend enough of it — he’s in trouble.

2) Does labor make an endorsement?

After the primary election, when Aguirre realized he would not be facing his longtime menace, Peters, he started actually trying to make nice with the council president. And some around town even wondered if Peters would support Aguirre. Others simply concluded that since Aguirre is a Democrat other Democrats who had supported Peters would naturally move to Aguirre.

These assumptions could have only been formulated by those unaware of the true animosity between Aguirre and Peters. The primary voters were few, but they were well-informed and motivated. Nobody who would want Peters to be city attorney would want Aguirre and vice versa. Sure, some might end up preferring Aguirre if he happened to be running against some kind of slimeball, but it was a real stretch to link the two because of their Democratic-ness. They represented vastly different worlds and have views about the city and the position of the city attorney that are simply irreconcilable.

And one big group in particular is dealing with this conundrum. The San Diego Imperial Counties Labor Council — the region’s union of unions — supported and worked hard to elect Peters in the primary. And, at the same time, the group displayed its disdain for the conservative politics Goldsmith displayed during his time at the state Legislature.

There were some indications the group would back Aguirre. But he has continued his long assault on the city’s firefighters union and others.

Big labor is one of the last groups not to take a side on this race. It has resources to buy publicity and lots of people to man phone banks. Does it stay on the sidelines or jump in?

Update: We have an answer. I’m told this morning that the Labor Council formally decided not to decide who to support in the city attorney race. The announcement was buried in a press release about the union of union’s recent endorsements. Both candidates are unacceptable, apparently, to the group. “Our members did not feel comfortable endorsing either candidate at this time given the unfortunate decisions they have both made throughout their careers,” said Labor Council Secretary-Treasurer and CEO Lorena Gonzalez, in the press release. More here.

So what does that mean? A non-endorsement is a win for Goldsmith. The conservative Republican had little chance to get the endorsement. But if Aguirre is trying to make this a partisan, Democrats vs. Republicans, race, he just lost a big opportunity to bolster his Dem credentials.

On the other hand, he could revert to his long claim that unions and the Labor Council are part of an establishment he is continuing to challenge. Not sure if that’s a winning argument but it’s definitely his type of argument.

3) How strong is Aguirre’s base?

The incumbent’s biggest strength is also his biggest weakness. He has tapped into a support base that will live and die with him because of one thing: He listens to them and reacts to what they say. No politician I’ve ever seen has so quickly reacted to residents’ complaints and grievances, whether they have emerged in the media, at community forums or in briefings with his staff.

The guy, in other words, reads the newspaper, hears about a supposed outrage and reacts immediately with all the power he has at hand.

This has earned him undying support from community activists who have never had a politician listen to them like that.

But this impetuous style has a big downside. It leads to an image of erratic behavior and lack of contemplation. He’s unable to pick his battles and that has led him to create enemies of all types. To Aguirre, every day is new filled with new outrages and new targets of his populist diatribes. The community activists who send him their complaints love it. But no individual can alone solve all the world’s ills. By taking on everything from global warming and the mortgage crisis to upsetting cutbacks at the local public radio station, Aguirre has had a hard time focusing his efforts.

I really do believe Aguirre sincerely is trying to help people and save the Earth. But while every day is a new day to him, the targets of his investigations and public vitriol of the previous day don’t let things slide so easily, and they’ve become passionate political enemies.

This makes a political campaign difficult. The major question for the fall is whether his base of passionate supporters is larger than the base of these fervent foes. Aguirre has to hope that his side is far larger than the 29 percent who voted for him in June.

4) Which message do the rivals seize?

There are lots of attack lines about the incumbent, but nothing has become the de facto message about why he should be turned out of office. Goldsmith and his campaign have been going about this the way traditional challengers in San Diego go after incumbents: By trumpeting daily supposed missteps with press releases and statements, and garnering endorsements by extension.

To unseat the incumbent, I would argue that Goldsmith needs a single coherent message that can both make people chuckle and communicate a disdain for Aguirre. This message has not yet emerged. Perhaps there are too many. Perhaps Goldsmith and his team sense that some of the most coherent arguments against Aguirre would unintentionally make Goldsmith seem like a lackey for the Establishment if he employed them. And that’s exactly what Goldsmith doesn’t want.

Aguirre, on the other hand, would be most successful by making Goldsmith seem like an unacceptable alternative. He has tried to make it a political, even partisan contest. He calculated that San Diego is more and more Democratic in its makeup and voting patterns. So, he thinks, if he successfully paints Goldsmith as a partisan conservative Republican beholden to the special interests that connotes, he can make him an unacceptable candidate.

Goldsmith has already anticipated this and reacted with a string of endorsements from prominent Democrats, including the one Aguirre was trying to make nice with: Scott Peters.

If Aguirre wants to beat Goldsmith, I think he’s going to want to find another line of attack.

5) The debates.

Aguirre and Goldsmith’s first debate was just ridiculous. It’s not hard to imagine news being made at the next. As Gerry Braun satirized it in Wednesday’s Union-Tribune, the debates could use some decency rules.

But if local politics interests you at all, you simply can’t miss them. Each one of the above dynamics about the race will influence the debates. But it’s in those head-to-head battles when we’ll see each for who he is.

Game on.

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

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