The day Tom Shepard met Jerry Sanders, they were both in the Mayor's office, and the lobby outside was filled with angry anti-abortion protesters. The mayor at the time was Susan Golding, the former county supervisor with an eye on higher political office. The year was 1996, and it was Aug. 9, the Friday preceding the Republican National Convention San Diego was hosting that year. The protesters, planning to demonstrate against Planned Parenthood clinics during the convention, were pissed about Golding's refusal to disallow the use of nunchucks as a non-lethal police weapon-used properly, the nunchucks can be clamped around a person's arm, forcing even the most reluctant activist to move. The protesters decided to test Golding's resolve by occupying her lobby.
"Most of her aides thought we should just arrest them all," Shepard said, 12 years later, sitting outdoors at Caffe Italia in Little Italy. "I said we should just leave them there. The only person in the room who agreed with me was the police chief, Jerry Sanders."
Golding went with Shepard and Sanders. The protesters sat there for hours, waiting to be arrested. At 5 p.m. a building manager politely asked them to leave. By then, only two remained, and Golding invited them to spend the weekend in her lobby. By the next day, the two had slunk off. Shepard and Sanders had scored their first team victory.
By that time, Shepard's career had reached a pleasant middle. He'd long ago left his youth and innocence on the beaches of Del Mar and in the courtrooms of San Diego. He'd suffered for years in limbo, and he'd struggled back to the peak, having guided Golding to victory over UC San Diego professor Peter Navarro. He still had years before him of helping well-funded moderate Republican candidates win elected office, not to mention steering initiatives that would fund expansion of the San Diego Convention Center and construction of Petco Park, culminating, at least for now, with the re-election of Sanders, his handpicked candidate in the wake of Dick Murphy's fall from grace.
His long string of victories and his connections to some of San Diego's wealthiest and most powerful residents has earned him the enmity of the political left. Navarro refers to him as "a tragic figure in San Diego politics," but others simply deride Shepard as a mudslinger. To the perception of many, he's the man pulling the strings behind many a puppet mayor.
Shepard's reputation doesn't bother him. If anything, he's amused.
"It's flattering that people think of me that way," he said, a slight smile crossing his face.
He has a little more time these days than he used to. Thin, neatly dressed in a button-down shirt and slacks, Shepard looks relaxed during an August in which he has no major campaigns to work; he has time to reminisce over past triumph and pain. His black hair has begun to gray, and his conversation is peppered with references to the lessons he's learned now that he has "reached old age." Having just turned 60, he has indeed slowed down his pace from his peak in the 1990s, when 14 campaigns in a given cycle was the norm. Having achieved a level of financial security rare for political consultants, Shepard can finally consider a slow winding-down of his long career.
Shepard easily remembers his first political moment, the event that pushed him into politics and gave focus to his benevolent, if vague, desire to "make life better for people."
As an undergraduate at UCSD in 1968, a friend of his who had volunteered for Democrat Alan Cranston's campaign for U.S. Senate invited him to the Ambassador Hotel in Los Angeles to watch the primary-election results roll in.
Cranston's victory in the primary was assured, but right-wing conservative Max Rafferty had been giving three-term incumbent Thomas Kuchel a serious race on the Republican side.
"When Max Rafferty beat him, we suddenly realized: we were going to win," Shepard said, sitting forward in his chair, his face animated with remembered excitement. "Because Rafferty was totally nuts."
Shepard even watched on TV from Cranston's suite as a crowd awaited Sen. Robert Kennedy's speech to thank his supporters for his dramatic victory in the California Presidential primary, and he saw the footage of Kennedy getting shot. He saw security drag assassin Sirhan Sirhan from the kitchen through the next-door ballroom, and he was questioned by Secret Service as they interviewed everyone in the hotel. The Secret Service wouldn't let anyone leave for hours, Shepard said. The adrenalin highs of the triumph and the tragedy of the night stayed with him. He was hooked.
Shepard lived in the then-popular student enclave of Del Mar. The sleepy beach town of the day bore as much resemblance to its future upscale self as a school board election does to a Senate campaign. At the time, students lived in low-rent bungalows and spent their days surfing or studying. Shepard studied, too, but he also ran for student council and then student body president. After graduating, still living in Del Mar, he decided to take his career ambitions up a level and run for Del Mar City Council. With the students as his base, he won, and his colleagues chose him to be mayor.
"I was probably too young," Shepard said. "People would come up to me in the supermarket and get all in my face. I had too thin a skin."
Shepard had won on a slow-growth platform, opposing the madcap pace of development that sent longtime residents into a panic over the possibility of "Los Angelization." Shepard and fellow City Councilmember Nancy Hoover had noticed the work of a young attorney named Roger Hedgecock who was passionately advocating for the creation of the California Coastal Commission. Shepard had known Hedgecock as the only reliable music promoter when, as student body president, Shepard organized some anti-Vietnam War concerts. Hedgecock had since gone to law school, and Shepard and Hoover decided to make him the city attorney.
"We wanted someone who could kind of push the envelope on these things," Shepard said.
Hedgecock swiftly built a reputation for himself as an environmentalist and a moderate Republican voice in a region populated by hard-line conservative politicians. In 1976, Hedgecock ran for county supervisor and won, defeating future Shepard antagonist Bruce Henderson. Two years later, Shepard would join Hedgecock as his chief of staff, never to run for office again. While Shepard remains proud of the work he did with Hedgecock for the county, particularly an influential report that highlighted the poor working conditions and healthcare of migrant workers, the slow grind of local bureaucracy did not suit him.
Shepard started a political consulting firm in 1981, with backing from Hoover and her boyfriend, J. David Dominelli, that added up to $357,000 over three years. After then-San Diego Mayor Pete Wilson's 1982 election to the U.S. Senate, Hedgecock decided to run for mayor of San Diego, and he hired Shepard's firm to run the campaign.
Hedgecock was considered the outsider competing against two entrenched figures-Democrat Maureen O'Connor, a friend of the unions and married to the founder of Jack in the Box, and William Cleator, a Republican with the full support of the Downtown elite. He beat them both.
"We had to go to the neighborhoods," Shepard said.
He and his partner, pollster Bob Meadow, carved the city into demographic chunks and crafted messages designed to resonate with specific groups of San Diegans: pro-environment for the beaches, anti-growth for the northern suburbs, pro-business for anyone Downtown willing to listen. The tactic allowed them to get around the establishment, beating Cleator in the primary and then, with Republicans unified behind them, beating O'Connor in the general election.
While Shepard didn't join Hedgecock's administration, he became part of an informal "kitchen cabinet," along with some university professors like San Diego State University professor emeritus Glen Sparrow.
"He doesn't just walk away at the end of the election," Sparrow said of Shepard. "He stays involved."
Indeed, Shepard's continued involvement with his candidates became a hallmark of his career. Even today, he says many of his clients will call him for an opinion in a crisis or with questions on how to craft the response to a particular issue. His work with Hedgecock made him the logical candidate to run the campaign to build a new convention center Downtown.
"The convention center had failed six times," Shepard said. "Even Pete Wilson couldn't get it done. Everyone always thought it would get laid at the feet of the taxpayers."
Shepard's insight was to persuade the Port of San Diego's Board of Commissioners to offer to build the convention center on their waterfront land, and then lease it back to the city. The move allowed Shepard to co-opt earlier opponents and win their endorsement. The initiative passed.
Then everything went to shit.
The financial firm that Dominelli and Hoover had used to get the cash to back Shepard's business turned out to be a giant hoax, a kind of Ponzi scheme pulled on San Diego's elite. Dominelli and Hoover were both convicted on fraud charges. But thelaw enforcement agents on the case traced the money Hoover had given to Shepard to Hedgecock, calling the funds an illegal campaign contribution designed to avoid donor-limit laws. Prosecutors charged Hedgecock with felonies and had to go through two trials before they got him on 12 counts of perjury and a count of conspiracy (though an appellate court later overturned them all, with Hedgecock settling for a single misdemeanor). Shepard found himself facing charges for his alleged role.
"They were using me to get to Hedgecock. I was facing 14 felony counts, and after he went down, they offered me a misdemeanor," Shepard said. "I ended up paying $1,000."
But the fine was the smallest price he paid. In what he would later call "the worst period of my life," Shepard lost all of his clients, including Golding, who was running for supervisor at the time. He struggled financially and had to accept work writing mailers for other consultants, often on the condition that no one knew he was doing the work. He started running small campaigns in New England, where he was unknown.
"I decided that I never wanted to be in the ethical gray area again," he said. "There are some consultants who still believe the ends always justify the means, but I'm not that way anymore."
But the scars of the Hedgecock trials went deeper than after-school-special morality. Shepard had been a fearless campaigner to that point, a San Diego "geranium" for a new era. In Del Mar, he'd fought a major development in Carmel Valley, and with Hedgecock, he was an environmental populist against entrenched interests.
"I think his career could have had a wonderful arc to it," said Navarro, now a professor at UC Irvine. "The core problem there is that Roger got railroaded and Tom understood the unfairness of it, and it turned him into somebody who became bitter and disillusioned."
Shepard spent his entire post-Hedgecock career working with exactly those Downtown elites he once fought. To Navarro and San Diego's coterie of progressives, he had "joined the dark side." Shepard would contest the notion that he is bitter, but not that he has made a habit of picking well-funded candidates, or, as he phrased it, "candidates with the resources to win." Shepard needed eight years to make his way into the establishment, and once there, he never left.
In 1987, he joined consultant Larry Remer and neighborhood activist John Hartley to win a campaign in favor of district-by-district elections for City Council, rather than citywide, and then to help Hartley win his seat on the City Council against the far-better-funded Gloria McColl. Remer remembered Shepard the Del Mar mayor fondly from Remer's own student radical days. Remer had organized a protest to block a trainload of munitions from reaching the Port of San Diego by blocking the track in Del Mar. The police showed up and the situation threatened to get ugly until Shepard intervened. After their win with Hartley, Remer invited Shepard to be his partner in a consulting venture they called The Primacy Group.
Shepard began to form his new legacy during his four-year partnership with Remer. In 1991, the pair helped activist Valerie Stallings defeat incumbent City Councilmember Bruce Henderson.
"He isn't afraid to get extremely negative," Henderson told CityBeat. "He will pretty grossly misrepresent positions for political purposes. That's part of the hardball."
Henderson believes Shepard is all too willing to sink to the lowest level of politics by boiling nuanced positions into negative-sounding mailers and advertisements. It's an accusation Shepard often hears: In 2002, a San Marcos City Council member accused him of using push polling against him, and in 2005, mayoral contender Donna Frye complained to the Union-Tribune of Shepard's willingness to distort her positions. (These days, Frye says she doesn't "think about Tom Shepard").
Shepard sees negative ads as just another tool in his toolbox.
"Everyone says they're against negative ads," he said. "Except that if they're accurate, and if they're fair, they work."
After the Stallings victory, The Primacy Group landed Golding's mayoral primary campaign and got her to the runoff against Democrat Peter Navarro. Golding changed agencies to the hot public-relations firm of the time-Stoorza, Ziegaus, Metzger & Hunt-and she insisted they hire Shepard. He jumped at the chance.
"It happened relatively suddenly," Remer recalls. "But that was his way back into the establishment. He never looked back."
Now on the inside, Shepard found himself working alongside George Gorton and two other consultants. Scott Barnett, who worked for Shepard at the time, recalls Gorton's screaming temper and the competition for Golding's ear. But he also remembers Shepard creating what would become a signature ploy: Chase mail.
"I don't think anyone had done that before. Now it's standard," Barnett said.
Shepard had started courting absentee voters all the way back in his 1972 Del Mar campaign.
"You can't depend on students to remember Election Day; they're too busy getting stoned on the beach, or studying or whatever," Shepard said. "So I devised all these goofy ways to get them registered with absentee ballots and to get them to send them in."
In 1992, backed by Golding's substantial fundraising (she would spend twice as much money as Navarro on the campaign), Shepard could be more sophisticated, but he was doing essentially the same thing. A programmer would go to the Registrar of Voters office and get the name and address of every voter planning to vote absentee. Then, three days after the absentee ballots were mailed, the campaign sent out mailings targeted just to that group of people. The procedure is expensive, since the mailing is so much smaller it has to go out via first-class mail.
"There are people who debate the effectiveness of that, but I think almost every election I've won, we've won the absentee vote," Shepard said.
When Golding won, Shepard was back as the dean of local political consultants. But having worked so hard to get that reputation back, he stopped taking outsider campaigns.
During the next 15 years, Shepard solidified his reputation as a consultant who wins. Asked what he did to win so many races, the consensus view of other political consultants was "choose candidates likely to win."
"The most important part of consulting is to have good candidates," said recently retired consultant John Kern. "Tom's been very fortunate to have good candidates."
With the Golding victory in hand, Shepard once again became part of a "kitchen cabinet," staying in weekly contact with Golding or her staff. When the Republican National Convention came to town, he was part of the planning effort, which may be why he was invited to the office to help deal with those protesters. Shepard's close association with Golding, along with a string of successes such as getting Dianne Jacob elected to the county Board of Supervisors, had finally gotten him connected with San Diego's major establishment figures. In 1997, he was hired to run the campaign to finance the expansion of the convention center, and that spring, Padres owner John Moores and team president Larry Lucchino hired him to run the campaign to sell bonds to fund a new ballpark.
Taken together, Shepard figured he could construct for voters a year-long narrative around redevelopment.
"The trick was to persuade the suburbs that these would be good for them," he said.
At that point, Downtown's resurgence was well on its way, and Shepard created a narrative linking the convention center expansion with the continued urban rebirth, a move that generated the right kind of buzz in San Diego's northern precincts. But the ballpark was still a problem.
"We were polling 37, 38 percent," Shepard said. "We had to figure out how to get over that. Then we decided to poll on locations. The Downtown location polled at 60 percent, because of its connection with redevelopment. So we spent the summer doing this kabuki dance: Lucchino pushed for a stadium by the sea, Moores for a Mission Valley site, and Golding for Downtown. Eventually we gave in' to Golding."
This period was possibly the busiest of Shepard's life. He would work 14 or 15 campaigns in a given cycle. In addition to working on the ballpark and the convention center expansion, he also was working on Golding's primary campaign for U.S. Senate, from which she eventually dropped out.
Shepard never did well in party-oriented campaigns. Some, like Navarro and Henderson, think it's because he simply isn't a good enough consultant to win those races. Shepard believes his own politically moderate stances make him a perfect fit for the nonpartisan city and county races.
"I figure, when you have a partisan campaign, you have 10, 15 percent of the undecideds to work with," Shepard said. "But in a nonpartisan campaign, you have everybody."
Shepard refused to be pinned down on his own personal politics, but he clearly seems to dislike the far left and the far right of the political spectrum, the people who form the base of any partisan electorate. The pro-business, right-leaning moderates seem to match his own view of politics.
Golding's Senate loss would mark the start of yet another downturn for Shepard. In 2000, he lost an attempt to get Brian Bilbray reelected to Congress, and he ran Ron Roberts' losing campaign for mayor of San Diego. In that campaign, Roberts had accepted free tickets to Padres games, and he'd flown in Moores' private jet. Roberts was tarred as a tool for the rich and defeated by then-Judge Dick Murphy.
Shortly after these high-profile defeats, Stoorza, Ziegaus, Metzger & Hunt closed down its practice. Shepard took over both the campaign division and its lobbying arm. The firm, now called Public Policy Strategies, has at various times represented high-profile clients like Sempra Energy and Wal-Mart and currently represents Poseidon Resources (the company building a desalination plant in Carlsbad), San Diego State University and The Home Depot. Shepard himself is not a listed lobbyist with the city of San Diego, and he says he never lobbies clients he elected, and, in particular, he agreed with Mayor Sanders that he wouldn't lobby him.
"I don't have any involvement with Public Policy Strategies besides what's required for my ownership stake," Shepard said.
The firm currently has two employees registered with the city as lobbyists. Other political consultants aren't as sure about how effective that divide between Shepard the consultant and Shepard the owner of a lobbying firm can be.
"I don't lobby my clients, and nobody in my company lobbies my clients, because I believe it's a conflict," said Remer, Shepard's former partner. "How can you trust the advice I'm giving you if I'm being paid by somebody else to give it to you?"
Conversely, Remer doesn't see how having an employee of Shepard contact Sanders' office on an issue is all that different from having Shepard himself do it.
"I don't see any difference," he said. "To say that somebody on my payroll is lobbying them and it's not me, to me that's a distinction without a difference."
In general, lobbying has the advantage of avoiding the boom-and-bust cycles of political consulting, and there's also the potential for earning far more money than political campaigning.
With the cushion of Public Policy Strategies and the electoral success of Scott Peters and Brian Maienschein in their bids for City Council in 2000, Shepard's early millennium wasn't nearly as painful as the middle-1980s had been.
San Diego's now-infamous pension scandal swallowed Mayor Murphy, forcing him to resign in summer 2005. While Deputy Mayor Toni Atkins managed the city's bureaucracy, there was a special election for mayor. Shepard knew the city would need a candidate with unimpeachable character, and preferably an open, likable personality to contrast with the departed Murphy. Shepard remembered that moment with Sanders in Golding's office, and he remembered that Sanders had helped devise a security plan for the convention in which, as the Union-Tribune reported, not one protester was arrested throughout the event. When Shepard called Sanders, the future mayor was on vacation in Washington, D.C., with wife Rana Sampson. The couple made an early return, and over dinner in San Diego, Shepard convinced Sanders to run.
In Sanders' campaigns of 2005 and then 2008, Shepard pulled together all the skills and resources he'd developed in 30 years of San Diego politics. Sanders, though the former chief of police, was relatively unknown compared with his Democratic opponent, City Councilmember Donna Frye, and had far less money to spend than millionaire Republican Steve Francis. Shepard publicly positioned Sanders as an outsider candidate untainted by the pension scandal, even as Sanders collected campaign contributions from San Diego's development establishment. Once Sanders survived the special election that eliminated Francis, he had little trouble defeating Frye with the combined Republican vote behind him (almost a repetition of the Hedgecock-O'Connor campaign of 1983).
With Sanders in office, Shepard resumed his policy of staying involved. He asked Professor Sparrow to serve on the transition team. In addition, Sanders hired one of Shepard's friends, Fred Sainz, as his spokesman, though Sainz said Sanders was the one who picked him out even before he won the race. Another close mayoral advisor, Kris Michell, had worked with Shepard in getting the ballpark initiative passed.
Shepard stayed in weekly contact with the Mayor's office, mostly through Sainz, but occasionally through Michell or talking to the mayor himself.
"Sometimes we'd talk about what was going on, but mostly it was to gossip," Sainz said. "A lot of times, I'd reach out to him or he'd reach out to me on certain issues and how these issues were playing out, or just to gossip."
Sainz recalled consulting Shepard on how to handle sewer-water recycling as an issue.
"He has a lot of clients and a lot of polls," Sainz said. "He usually had a pretty good idea of what people were thinking and talking about."
Shepard was also called in to advise the mayor when he was considering whether or not to support the City Council's letter of support to the California Supreme Court on the question of gay marriage. Sanders has a daughter who is a lesbian, and he was considering changing his position to one of support for the resolution. Shepard said he himself favors gay marriage but counseled against it for fear of losing the support of the Republican right against the notoriously conservative Steve Francis (before his political makeover).
"To his credit, Jerry ignored me," Shepard said. "But I had to spend the next three months repairing the damage."
This year, Shepard had the advantage of an incumbent client, but he had to help Sanders fend off the challenge of Francis, whose campaign spent $5 million, even as Sanders promised not to take money from anyone with business before the city. To get Sanders elected, Shepard crafted a message that emphasized Sanders' leadership to an electorate that already knew him as mayor, and he focused heavily on chase mail. But in the end, it may have been Sanders' position on gay marriage and the support he won from the gay community that guaranteed him reelection and no runoff.
Though the Sanders campaign absorbed his time, it was one of only a few campaigns Shepard ran this year, along with cakewalk reelections of two county supervisors. He has no plans to retire, but he does see himself doing less and less as the years progress.
"I'm definitely dialing it down," Shepard said. "But I'll be around a while yet."