San Diego’s primary election isn’t for three months, but who will advance to the runoff in the race for city attorney could be decided next week.

That’s when the local Democratic Party will choose whether to endorse one of the four Democrats running.

Local parties are allowed to accept contributions from individual donors that exceed the limitations for individual candidates. Parties can spend that money to communicate with their registered voters – not just through the mail, but through email and door-to-door campaigns, too.

“It’s a substantial advantage,” said Tom Shepard, a political consultant running Gil Cabrera’s campaign.

But it’s Cabrera’s rival, fellow Democrat Rafael Castellanos, who has the best chance at winning that endorsement.

As the vote approaches, it’s become clear that a win for Castellanos is getting the endorsement. A win for Cabrera – and Deputy City Attorney Mara Elliott – would be to convince the party not to endorse anyone.

Deputy District Attorney Robert Hickey is the lone Republican on the ballot. With the support of his party, and most of its network, he’s likely to make it to the November general election.

That means the drama of the race over the next three months is among the four Democrats – and especially among the two candidates who have put themselves in the strongest position, the port commissioner Castellanos and the former chairman of the San Diego Ethics Commission Cabrera.

“Going into it, our goal would have been – and we would have been happy – if nobody got an endorsement,” said Bill Wachob, the consultant running Castellanos’ campaign. “Then we started collecting endorsements, and we saw he has a good base of support with central committee members.”

But the fight is far from over.

Angling for the Endorsement

Castellanos has a simple pitch for himself as the obvious choice for the Democratic Party: Every Democratic club in town that has endorsed a candidate has endorsed him.

He got there, in part, because so few people know anything about the Unified Port of San Diego, where he’s a commissioner.

The City Council appointed Castellanos port commissioner at the beginning of 2013. He said he already knew then that he wanted to run for city attorney.

When Wachob and Castellanos started talking about how Castellanos could position himself as a citywide candidate, they realized he could go on a tour to explain what the Port does. It would double as an effective campaign.

“He used it as a chance to get out there and talk about it and himself, and I don’t know what other candidates were doing at the time,” Wachob said.

Cabrera’s team also recognized Castellanos’ position on the Port as a substantial advantage.

“He’s a sitting port commissioner – that’s as close to an incumbent insider you can get without being elected,” Cabrera said. “He’s been saying for a while, ‘Gosh, look how good I’m doing, I’m just a street lawyer and look at all the money I fell into.’ But really, I don’t think anyone is surprised a sitting port commissioner can raise significant money.”

It’s typically pretty tough to raise money for city attorney races, Shepard said. The city attorney has less direct influence than City Council members or the mayor over decisions that might be important to a donor.

“This is a bit different for (Castellanos), as a port commissioner and developer attorney, he has access to major donors and he’s done a good job taking advantage of that,” Shepard said.

But Cabrera has his own path to campaign cash.

He is a longtime member of – and at one point coordinator for – an informal Democratic fundraising group called the 745 Group. It was started by longtime Democratic donor Murray Galinson and often convenes fundraisers when national candidates like Hillary Clinton come to town.

Wachob said he knew Elliott would not raise much money.

“But we were always kind of surprised when we saw that we had outperformed (Cabrera), especially early on,” Wachob said. “We saw this La Jolla crowd. He had built a network. And it wasn’t a secret he would be running for office.”

Jostling on the Left

Cabrera and Castellanos have raised the most money and collected the most endorsements of the four Democrats. Cabrera brought in more than $200,000 last year and had $130,000 to spend at the beginning of the year. He’s gotten endorsements from City Councilman Todd Gloria, Assemblywoman Lorena Gonzalez and former Assembly Speaker Toni Atkins.

Castellanos has brought in more than $300,000 and started the year with more than $230,000 to spend. While his highest-profile endorsements came from out of town – Lt. Gov. Gavin Newsom and Attorney General Kamala Harris – he also has the support of City Councilman David Alvarez.

Environmental attorney Bryan Pease was a late entrant into the race. He’s got some citywide fame from high-profile lawsuits he’s filed against the city, and from running for City Council four years ago. But so far he hasn’t received many endorsements, and he hasn’t had to file any campaign finance disclosures yet to show how much he’s raised.

Elliott has the pedigree and endorsements of a serious contender – she’s a senior employee in the office that she’s running to lead and she’s received endorsements not only from the union that represents rank-and-file city attorneys, but also City Councilwoman Marti Emerald and former City Attorney John Witt.

What she doesn’t have, though, is money that would let her stand toe-to-toe with Cabrera and Castellanos: Through the end of 2015, she’d raised just $50,000, and had just $35,000 available to spend.

Money is always a separator in political races, but it’s even more important in a race like city attorney, where relatively few voters know what the position does and even fewer have any familiarity with the candidates. It’s expensive to make sure voters citywide know who you are, your party and your qualifications.

And that’s where support from a county party becomes so crucial.

How it Will Go Down

The San Diego County Democratic Party is affiliated with a network of 36 clubs around the county, either organized by neighborhood – like the Point Loma Democratic Club – or by issue – like Democrats for Equality.

Ten of those groups have endorsed Castellanos. The rest either voted not to endorse anyone, or haven’t voted yet.

Not only does that make it easier for Castellanos to appeal as the choice of the party’s grassroots groups, but many of the chairs of those individual groups are part of the party central committee. They aren’t obligated to vote along with their group, but it’s one more thing to consider.

“I wouldn’t equate his support with being the most liberal,” said Wachob. “I think it shows he’s the hardest-working candidate, and some of the other candidates have frankly been pretty lazy about it.”

Cabrera’s team said Castellanos’ club endorsements are misleading. Many of those were small clubs outside the city, and Cabrera says Castellanos’ team paid for people to become members of the clubs specifically to vote for him.

Cabrera’s team instead focused on appealing to the largest clubs in the city, like Democrats for Equality, the Clairemont Democratic Club, the Point Loma Democratic Club and San Diego Young Democrats. Those groups opted not to endorse any of the candidates.

“Anyone paying attention to the race would be hard-pressed to say he outworked us,” Cabrera said. “A lot of organizations are waiting to see what happens in June, and with four Democrats in the race that’s not surprising.”

Making a Citywide Case

Elliott hasn’t raised nearly the money as Cabrera or Castellanos. But she has a different kind of advantage.

Not many people know what a city attorney does, or what they should look for in a candidate. In such low-information contests, the tag-line describing your profession might be all a voter knows about the race.

It’s hard to beat Elliott’s ballot title: chief deputy city attorney. The office she’s running for is right there under her name.

Plus, she’s the only woman on the ballot, a potential advantage, especially among women voters.

It’s possible, then, that she’ll need less money than the other candidates to make her case, since she’ll have something of a head start.

That was partly born out in an internal poll the Elliott campaign released last month.

It showed 64 percent of voters are totally undecided on the race. But it also showed that once respondents heard each candidate’s resume, Elliott jumped to second place, with 26 percent support. Hickey clocked in at 32 percent support. Pease and Castellanos had 16 percent support each, and Cabrera had just 6 percent support.

Shepard said the poll was consistent with his own internal polling in one important area: the share of voters who remain undecided.

But he said his poll also raised the possibility that Hickey isn’t a lock to get through June.

“Without respondents being told substantial positive information about Hickey, he didn’t do well,” Shepard said.

Hickey’s campaign said it is focusing on making a nonpartisan case for him and emphasizing his law enforcement support.

Shepard and Wachob concede that Elliott has a built-in advantage. But they think it is likely to disappear once voters see campaign materials from those with enough money to spend.

It looks like three candidates will have enough money to run a full citywide campaign. Hickey has raised a total of $182,000 and has $100,000 unspent. He’ll also have the support of the local Republican Party, potential independent expenditures from the Lincoln Club, a conservative group political action committee, and a host of prosecutor and law enforcement groups.

But Cabrera said he won’t need as much money as Castellanos.

That’s because, Cabrera said, Castellanos won’t be able to spend money just introducing himself to voters. He’ll also need to spend money responding to accusations about his past.

In 2010, an attorney at the firm Castellanos was working for filed a lawsuit alleging sexual harassment against the firm, specifically naming Castellanos for pressuring her to have sex with him. The case settled a year later. Castellanos didn’t pay anything in the settlement, and didn’t admit to any wrongdoing. The woman received one month’s severance pay in the settlement, paid by the firm’s insurance carrier. Voice of San Diego delved deeper into the case late last year.

“He is going to need more money because he is going to have to respond to allegations, including the one covered by Voice of San Diego,” Cabrera said.

Shepard said any dollar spent on that will be a dollar Castellanos can’t spend leveling attacks of his own.

“It’s either going to have a major role in June, and he won’t survive, or he’ll get through and it we’ll defeat him in November,” Shepard said. “I think the Democratic Party needs to do some soul searching among its members about where they want to take the party.”

Wachob reiterated that Cabrera has been outworked by Castellanos.

“There is no excitement about his campaign and maybe that is because he is really more like a Republican,” Wachob said, criticizing Cabrera for having a relationship with the San Diego County Taxpayers Association, a right-leaning organization, and for seeking the endorsement of the Lincoln Club.

He said Shepard’s attacks were hypocritical and have helped Castellanos raise support.

“It’s also interesting that Tom Shepard would raise the sexual harassment allegations issue, he being the gatekeeper to the Bob Filner campaign and his early months as mayor,” Wachob said. “Their attacks have been backfiring since they first started slinging that mud in 2014.”

Andrew Keatts

I'm Andrew Keatts, a managing editor for projects and investigations at Voice of San Diego. Please contact me if you'd like at

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