Aug. 8 2012 10:10 AM

The San Diego mayoral race gets weirder

Tom Shepard, Art Castanares

"No matter how cynical you become, it's never enough to keep up."

—Lily Tomlin

The recent post-primary mayoral-race moves of Republican campaign strategist Tom Shepard to Team Filner and former local Democratic Party chairman Art Castañares to Camp DeMaio has political heads spinning.

Spin Cycle, meanwhile, tried to take the news in stride in a political environment whose tectonic plates seem now in perpetual shift. Just what, Spin thought, are these moves all about, and what are the plusses and minuses of each decision?

Let's start with Shepard. As Spin wrote a couple months ago, Shepard had suggested that if Bob Filner softened his negative rhetoric, in essence, on public-employee-pension reform and the bayfront Convention Center expansion efforts by local hoteliers, then there was a chance that he could woo Shepard's former client, Republican-turned-independent Nathan Fletcher, to his side.

Little did Spin know at the time that such political compromises, which Filner made, would eventually attract Shepard himself into taking on the consulting duties for the Filner campaign. But with Shepard facing the prospect of having no mayoral candidate in the fire heading to November for the first time in a long time—he was strategist for two of San Diego's last three mayors—it shouldn't be completely surprising.

To some, it's a brilliant move on Filner's part: Counter Carl DeMaio's perceived political intransigence on a variety of issues with a demonstration that Filner's legendary prickly hard-headedness as a member of Congress will take a back seat when he occupies the mayor's chair.

Others suggest perhaps a less-than-altruistic reason for Shepard to join Team Filner. Shepard is part owner of Public Policy Strategies, a local lobbying firm whose clients include the San Diego Police Officers Association and San Diego State University. Without the shot with Filner, Shepard would find himself scrambling for effective access at City Hall in the future.

Shepard called such a suggestion "offensive to a staff that is trusted at City Hall to tell the truth."

What Shepard does bring to the Filner campaign is a visceral distaste for DeMaio. As the U-T San Diego noted in its story about Shepard's decision, "he just couldn't sit back and watch DeMaio become mayor because he knows ‘how much damage a destructive personality can do to an institution'"—a nice way to say that DeMaio's aggressive tactics and animosity toward public-employee unions are ill-suited to run a large city.

But some political observers also wonder if the addition of a Republican consultant so embedded in the politics of the past is a good fit for Filner, whose campaign boasts both his outsider status in city government and insider knowledge of problem solving.

"I just worry that it's the first foot in the door of the establishment that has been running San Diego for so many years," said former state Sen. Steve Peace, who serves as co-chair of the Independent Voter Project, a nonprofit dedicated to putting an end to political polarization. "We can all argue whether we like Bob or Carl, but nobody can argue that either are of the establishment.

"And that's what's needed in this town, a little creative destruction. In my mind, bringing on Tom says Bob has decided he needs the establishment. And that's disappointing to me."

Conversely, what does the addition of Democratic consultant Castañares bring to DeMaio's campaign?

At least initially, a whole lot of blowback from local Democratic leaders, for one.

Jess Durfee, who's wrapping up an eight-plus-year stint as chairman of the San Diego County Democratic Party, likened Castañares to a "used-car salesman" and snidely wondered how much he was getting paid to join the DeMaio team.

"I can't imagine DeMaio paying him very much, because, to be honest, anything is probably too much," Durfee told Spin Cycle.

Durfee even went to the trouble of issuing a press statement when the Castañares hire was announced last week. "From Art's ethics breaches to his legal entanglements, he doesn't exactly embody the ‘reform' that the DeMaio campaign has been promising," Durfee jabbed.

To his credit, Castañares has not withered from the avalanche of criticism heaped upon him for joining the DeMaio camp. He told Spin that he's less surprised by the shots themselves—"I knew they would be coming"—than he is by the venom used to deliver them.

Yes, he's had run-ins with the San Diego Ethics Commission over late filings of his lobbying activities in 2007 and 2009, but he described those as clerical errors more than anything.

As the operator of several business ventures over the years, he's had his share of legal disputes, but he says he's never lost a case.

A 2009 complaint filed by the Securities and Exchange Commission that appeared to link him, as CEO of Four Square Productions, to convicted South Bay Ponzi-schemer Moises Pacheco was later dismissed because, he said, "we had documents proving that we paid back the loan. I had no idea that Pacheco was involved in other things."

The SEC complaint alleged that Pacheco had "wired $960,000 in November 2006" to Four Square Productions, a Kearny Mesa-based film company whose shares Castañares had earlier purchased from Peace, who'd first hired Castañares as an intern in high school before promoting him up the ladder over 13 years to chief of staff. Peace offered "no comment" when asked about his relationship now with Castañares, suggesting some hurt feelings.

In 2007, Castañares shuttered Four Square, which in its early days was the launching pad of the popular Killer Tomato film franchise (since split off into another company held by Peace). Castañares said simply that times had changed for film-production companies. "You could make a film on an iPhone," he noted.

Castañares, as head of Manzana Energy, is also embroiled in a lawsuit with the San Ysidro School District over an $18-million contract to top school buildings with solar panels. He predicted that issue will be resolved soon, and "you'll see who the good guy is on that."

In the end, it's hard to know if such political hires will be game changers. It's just interesting that they happen.

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