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During 1988, Reilly was paid more than $6 million by the automobile insurance industry to run two statewide anti-consumer initiatives. In the spring of that year, he bought a mansion in Sea Cliff for $2.3 million, and in 1992 became a landlord, paying $3.9 million for an office building on Pacific Avenue in North Beach that became the start of his commercial real estate fiefdom.
In 1993, Reilly was awarded what he says was a $600,000 settlement after San Francisco Examiner Editor Phil Bronstein allegedly broke his ankle in a scuffle that erupted during a meeting with Publisher Will Hearst. (Both men have their own versions of the scuffle's origins.) Reilly believes the pain-filled incident marked a turning point in his previously charmed consulting life. The media was no longer entirely friendly toward him, he says, and a four-year streak of winning campaigns ended.
Reilly's ship went to ground on Kathleen Brown's 1994 gubernatorial campaign. When she lost by a landslide to Pete Wilson, a Greek chorus of pundits blamed Reilly for her defeat. Then, in 1995, Reilly ran the failed re-election bid of San Francisco's incumbent Mayor Frank Jordan against the outgoing speaker of the state Assembly, Willie Brown. Jordan lost after he spontaneously took off his clothing and allowed his picture to be taken in a shower with two naked radio DJs, spawning universal expressions of incredulity.
Reilly retired as a political consultant. Despite the late-career defeats, he is recognized by his peers as a pioneer in the business of campaign management. He and his full-time staff ran a profitable, full-service operation that did everything from raising campaign funds to printing and mailing brochures to writing speeches and producing television commercials. Reilly excelled at providing what may be the most important service of all: developing a simple, believable message on which a candidate could focus his media barrage.
He had another talent. In honor of his ability to create negative images for opposing political candidates, his associates nicknamed him "Satan." It was a negative image his opponents resurrected -- to startling effect -- in deflating Reilly's initial run for mayor.
Although he's out of the business, Reilly loves to explain the mundane science underlying the seeming magic of political consulting. Before the advent of television, he says, people elected leaders who, they believed, possessed uncommon knowledge about public affairs and a talent for governance. "These leaders were like Old Testament prophets who navigated the crises for the people," he says.
Inside the mass media barrage of the present-day election, however, people are "deluded" into believing that they -- the voters -- possess significant knowledge about reality and governance (when they do not). Therefore, Reilly says, they vote for the candidate who they think agrees most with them. Modern campaigns are intended to hook into people's fears, insecurities, and prejudices, not their hopes.
"Media bombards you," remarks Reilly. "You do not comprehend it as it changes the way you think; voters are empowered in their own minds to believe they are in control of the issues. The political consultant does not put out anything new; rather, he strives to resonate with people's previously held ideological convictions, such as about the death penalty, abortion, taxes, crime, education.
In 1995, Reilly moved to improve the quality of his own life. He married his girlfriend, Janet Koewler, a public relations professional who worked for a former Reilly client, Richard Riordan, the mayor of Los Angeles. And he bought the 16-story Merchants Exchange Building from Shorenstein for $18 million. It turned out to be a brilliant investment; the building may now be worth as much as $70 million. Reilly also owns an office building in Sacramento. He says steady income from his commercial office rental holdings gives him the freedom to serve the public.
"Citizen" Reilly replaced Satan.
"When I started out in 1970," Reilly says, "I thought I could elect good people who could do more than me by myself. I thought I could multiply myself and my convictions. In the Christian community, the priest is not really a leader, but a facilitator of leadership. My idea of a political consultant in the absolutely best sense was as a facilitator of leadership. I left the profession because people think of political consultants as Machiavellian, as necessary evils. I decided I could have a greater impact on social change by becoming a leader myself, as opposed to a facilitator of leadership."
Reilly's first foray into citizen politics was financing and quarterbacking a barely losing campaign against Willie Brown's proposition to build a "stadium-mall" for the 49ers football team. (When 49ers then-owner Eddie DeBartolo pleaded guilty to a federal bribery count in Louisiana in 1998, the stadium-mall deal died.)
In 1999, Reilly announced the birth of his daughter, Jill, and his candidacy for mayor. He sold stock and took out loans on his buildings to finance his $4 million campaign, which he lost with 12.5 percent of the vote after ex-Mayor Jordan and Supervisor Tom Ammiano jumped into the race at the last moment -- and after a charge that Reilly had a history of abusing women was splashed all over the front pages of the papers.
"Losing the mayoral race was humiliating and embarrassing, but losing is part of winning," Reilly sighs.