Darth Vader meets the Worst Person in the World: Pulling back the curtain on the mayor’s race

The San Diego mayor’s race was expensive, hard fought and by most standards, nasty. The campaign strategists — the men behind the candidates — are paid to shape the persona and mould the message.

The Bob Filner and Carl DeMaio campaigns hired some of the best. One has been called the Darth Vader of politics, the other, the Worst Person in the World.

Both sat down with inewsource and opened their play books.

Tom Shepard looks tired.

As Bob Filner’s chief strategist, Shepard has spent the last three months crafting the Congressman’s campaign for mayor -- as well as anyone can craft a man as infamously hard to handle as Filner.

“I haven’t succeeded in moulding him at all,” Shepard said with a laugh.

Seated behind a large desk with a view overlooking Bankers Hill, he reflected on this mayoral campaign — one he parachuted into midstream; one which elected a man Shepard didn’t support in the first place; one that has cost him his 30-year relationship with the Republican Party.

“Clearly Bob was not my first choice in this race,” he said.

But Filner was, he explained, the only choice.

Shepard began his political career as an idealistic 23-year old college student, who later worked as a volunteer on political campaigns and eventually became mayor of Del Mar.

He swept that conversation aside, as if it wasn’t even worth the time.

That’s the kind of guy he is.

Shepard engineered campaigns for the building and expansion of the Convention Center and Petco Park, the city’s adoption of the strong mayor form of government, and the election of numerous city councilmembers, sheriffs, supervisors, treasures, and more than a handful of mayors both in San Diego and in the surrounding area.

He’s as polarizing a figure in the political consulting world as Filner and Carl DeMaio are in the electorate. He’s been called a “Mayor Maker” and “the most successful political consultant in San Diego history.” Others call him the Darth Vader of local politics, a man who will win at any cost.

Shepard started out the 2012 election season strategizing for Assemblyman Nathan Fletcher, a Republican-turned-Independent who created huge buzz but couldn’t make it through the primary in the race for San Diego mayor.

When it was down to Filner and DeMaio, Filner, a lifelong Democrat, approached Shepard — who then thought long and hard about the repercussions. His last three San Diego mayoral campaigns had seated Republicans in the office.

Shepard said political strategizing is a business, very different from personal advocacy. But he couldn’t sit this one out.

“I felt, as many San Diegans probably did, that [Filner and DeMaio] were not my two choices for mayor,” he said, “but we still had to make a choice.”

“Given that choice,” he said, “this was the right thing to do.”

DeMaio’s campaign strategist would disagree.

“Tom Shepard has the benefit of not having any soul when it comes to ideology,” he said.

This coming from the worst person in the world.

The losing side

When a friend called late one night to tell Jason Roe that political commentator Keith Olbermann had just labeled him the worst person in the world on national TV, Roe had one question:

“Did they use a good picture?”

That’s the kind of guy he is.

The 42-year old founding partner of national consulting firm Revolvis is confident, by admission juvenile, successful, relatively young for his profession, and worst of all — smart.

His company refuses to take on liberal clients, and in doing so, suffered a trouncing this election day between the firm’s 20 politicians. He’s not sure who he’ll take on in the immediate future, or what he’ll do.

Snowboarding in Tahoe isn’t out of the question.

What went wrong on Tuesday, according to Roe, was he and fellow Republican strategists failed to expect the overwhelming under-30 voter turnout. The firm bet low and lost.

But DeMaio’s loss clearly agitates him.

Roe and DeMaio knew each other somewhat during their parallel lives on the East Coast, when DeMaio ran The Performance Institute in D.C. Roe helped DeMaio by arranging for Congressmen to speak at the for-profit think tank.

Roe saw potential in DeMaio, and he admired him.

More than a decade later, on June 1, 2011, Roe’s firm signed on to its first major San Diego campaign: Councilman DeMaio’s run for mayor.

Parallel Paths

While the differences between the far-left Filner and the fiscally-stringent DeMaio were the highlight of many a campaign advertisement this election season, not much was said about their similarities.

And there are a few.

Both men are accustomed to getting attention by making noise, and lots of it — Filner as a Congressman, DeMaio as a minority member of a largely democratic San Diego City Council. The experiences made both men highly abrasive.

Both campaign managers coached their clients about that behavior. Both said their candidates matured personally and professionally in the process.

Both Filner and DeMaio made their campaign managers think long and hard about the costs of the job. Money aside, Roe was concerned about jeopardizing his friendship with Fletcher, who aided Roe and his wife in adopting a child two years ago. Shepard debated the all-too-real possibility of severing his hard-earned relationship with the Republican party.

Each candidate inspired a disdain in the other’s consultant that powered a personal reaction to get involved.

When asked about DeMaio, Shepard recalled a time when he was a “close observer” of former City Attorney Michael Aguirre, one of the city’s most outspoken and divisive figures.

“I watched how much damage an unstable personality can have on an institution,” he said. “I class DeMaio in the same category as Aguirre in terms of a destructive personality.”

When asked how DeMaio’s personality compared to Filner’s, Shepard said, “I've spent a good deal of time with both of them, and I'm working for Bob Filner.”

Shepard fears DeMaio would have done “serious damage” to the city government, although he preferred not to speculate about the particulars.

The fear of damage is contagious.

Roe, dressed in jeans and sandals and sipping an IPA in a Bay Park restaurant on Wednesday, became visibly irritated when discussing Filner.

“This guy is about to be given the keys to the castle, to San Diego,” he said, “which is just starting to get out of a financial crisis... and this guy’s got no plan, and he does not have the temperament to be a chief of staff.”

“Being one of 435 members of Congress,” he continued, ”there is only so much damage that Bob Filner can do.”

“I am frightened for the city of San Diego for what will happen when Bob Filner is mayor.”

Filner’s mistakes

Over the course of the campaign, Filner’s unapologetic indignation dug him into a few holes.

His flustered television interview with KPBS over port issues in April — complete with cellphone ringing mid-tape — set the stage for a slew of gaffes.

In opposing the Plaza de Panama plan at a City Council meeting in July, Filner raised more than eyebrows by introducing an imposter Kate Sessions, famed horticulturalist known as the Mother of Balboa Park, to help make his case. Many believe those theatrics cost him a key endorsement.

Filner’s refusal to come out on stage during a recent debate because he didn’t agree with the rules of the coin toss gave DeMaio time for a solo conversation with the audience.

Shepard knew what he was getting into. He’d been speaking with Filner about working on his campaign during the time of the Plaza de Panama hearing.

“After that happened,” Shepard said, “I sat him down and said ‘What were you thinking?’”

Shepard underscored what he’d been harping on for weeks: the difference between being an advocate, like Congressman Filner is expected to be, and being a chief executive, like Mayor Filner would need to become.

“He spent 20 years in Congress playing a role which was defined by the system he was in,” Shepard said, “which was, ‘Stand up for your constituents, express as strongly and effectively as you can your point of view, and try to get it to prevail.’”

“Those are admirable traits,” he continued, “but they’re a skill set for a different job.”

Shepard said, “I don’t think I’ve significantly changed [Filner’s] behavior at all,” yet at the same time he believes, “There has been an evolution in [Filner’s] thinking and approach.”

Filner’s transformation since hiring Shepard in August may have been difficult to detect, but DeMaio’s was more prominent, more measurable, and much more calculated.

A new science

While only 42 years old, Roe already has 25 years logged under his belt in the political arena, and he’s watched the consulting game shift over time.

“It used to be about 80 percent art and 20 percent science,” he said. “Today it’s 80 percent science and 20 percent art.”

Roe, along with two other Revolvis staff, began DeMaio’s campaign by polling the city’s voters, employing a strategy called microtargeting: an “exhaustive and in-depth” process of extracting voter behavior from consumer data.

This helped the campaign determine what issues those voters cared about, along with “what will move them on those issues.” They crafted their mail campaign around those issues, targeting specific voter clusters with different messages.

And then they did all they could to get Filner through the primary.

“We got involved in the primary in places to... help Bob Filner run the campaign that he was incapable of running for himself,” Roe said, “to help him get across the finish line.”

Revolvis did this by running TV ads, along with mailers, that attacked Filner for being too liberal. They sent the mail to registered Democrats.

“We had to,” Roe said. “The guy was killing himself.”

Running against Bonnie Dumanis or Nathan Fletcher would have been a challenge for DeMaio, since the two were centrist candidates more “comfortable and acceptable” to Democrats, according to Roe. The targeted ads aimed to solidify San Diego’s Democratic base behind the man Revolvis thought DeMaio could beat once he emerged from the primary.

Because DeMaio knew the issues “better than anyone in the city,” Roe said, debate preparations had “little to do with substance.” They were about style.

DeMaio, who had become shrill in order to be heard, was a quick study, Roe said. Revolvis worked on “polishing the edges.”

The rest was up to the ads.

Going negative

The infamous “I’m a Congressman, and can do whatever I want” line served as the salt and pepper of the anti-Filner campaign-- sprinkled over numerous ads and used liberally throughout. That line was taken from a nine-year old memo that purported to quote Filner in a confrontation with an immigration supervisor. Filner denies saying it.

“I find that ad to be very objectionable,” Shepard said, “notwithstanding my relationship with Filner.”

But Shepard’s campaign has crossed the line, at times, as well -- most notably when Filner falsely accused DeMaio’s partner of criminal involvement in the trashing of the Balboa Park lily pond a few months ago. Some thought it was a disguised attempt to highlight DeMaio’s sexuality.

Roe referred to this as “gay-baiting,” and believes it should be “appalling to the gay community.”

Shepard was working for Filner at the time.

“All I can say about that,” he said, “is there were things said that should not have been said... [Things] that were not vetted and were not based in fact.”

Revolvis sullied DeMaio’s image a bit with bad advice in April before a televised debate on KPBS.

The firm advised DeMaio to bring up an Ethics Commission investigation of Fletcher — without knowing that Fletcher was already aware the commission had closed the inquiry.

“That wasn’t Carl’s decision,” Roe said. He referred to the incident as “an awkward moment” — but one that didn’t leave “any lasting damage.”

While both sides claim to have adhered to the ethical standards for their industry, neither will deny the power of going negative. It’s simply too effective.

“For all those who decry it,” Roe said, “I’d tell them to take a look in the mirror.”

“It’s what works,” he said.

Roe even gave kudos to Shepard’s campaign for pushing DeMaio as “too extreme.”

“I could be extremely cheap or extremely generous,” he said. “Extreme becomes a subjective — you apply it to what you want it to be.”

Roe believes this tactic worked well on “low-information voters,” who were led to associate DeMaio with a subjective term that doesn’t actually mean anything.

“Toward the end,” he said, “it is the bluntest, most simplistic messages that are effective.”

The future

When Filner steps into his role as mayor, he'll be forced to do something he's never had to do while in Congress — delegate authority.

"I think his biggest challenge is building a team that he trusts," Shepard said.

Shepard has seen Filner "fight like crazy" with his Congressional Chief of Staff, Tony Buckles, but at the end of the day, he said, "Filner can back down and acknowledge the fact that he's wrong or that he needs to look at a particular situation differently."

Shepard doesn't know who Filner will recruit for his staff, but for the Congressman to manage effectively and listen to reason, it needs to be someone with a strong personality. And he needs to learn how to get along well with others.

"A mayor is successful not based on how strident their advocacy is," Shepard said, "but how effectively they can build coalitions."

"And he knows that," he continued. "I think he's beginning to put into practice that revelation."

Roe has serious doubts about that. Case in point was the morning after the election when Demaio attempted to make the traditional call to Filner.

“For Bob Filner to not even be willing to give Carl his cell phone number,” he said, “[in order] to call and say, ‘Hey, congratulations, good luck, let me know what I can do to help,’ was, I thought, pretty low.”

DeMaio’s recently retired campaign manager, Ryan Clumpner, confirmed the Filner campaign’s refusal to share the Congressman’s personal phone number with DeMaio early the morning after election day.

Instead, a call came in from Shepard, who told Clumpner that Filner would be the one to call DeMaio.

“I’ve never heard of the winning candidate insisting on being the one to make the call,” Clumpner said. “That is not a standard.”

As for DeMaio, he hasn't said what he'll do next, but Roe believes he will stay in politics.

"As bad as he is interpersonally,” he said, “he really feeds off this process."

"I think it energizes him, I think he's a student of it, and I think he wants to be good at it," he said, "and I think he's gotten good at it."

Finishing up the last of his beer, Roe said, "I don't think we've seen the last of Carl DeMaio -- by any stretch of the imagination."

We'll let you know when big things happen.
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