consultant

SAN FRANCISCO — Every election produces a campaign strategist whose victory bestows upon them, for at least a little while, the unofficial title of reigning political genius.

James Carville, Karl Rove, David Axelrod and Stephen K. Bannon have all worn the crown.

For many years, and many election cycles, California’s reigning political genius was Clint Reilly.

In an age before the internet, before social media, before the cable-TV chat shows and before Carville and the like, Reilly came as close to celebrity as a political operative possibly could. He was the subject of fear, admiration, contempt, envy and lengthy newspaper and magazine treatments.

His cherry-red Jaguar, Italian suits, designer eyewear and seaside mansion made Reilly an influencer before there even was such a thing. (A connoisseur of the finer things, he served visitors coffee in bone china when they called on his San Francisco office.)

“It used to be that political consultants and political mechanics were something that only a handful of people thought about,” said Eric Jaye, one of generations of campaign strategists who were trained or inspired — directly or indirectly — by Reilly. “Clint was the original star consultant who made news himself and shaped the political discussion.”

Reilly, a working-class product of Oakland who crossed the Bay and scaled the heights of San Francisco business, culture and politics, died earlier this month at age 79.

For someone who never held political office — a 1999 bid for San Francisco mayor was a notable flop — Reilly wielded considerable influence.

A list of the many Democrats he helped elect — among them Nancy Pelosi, Dianne Feinstein and Barbara Boxer — reads like a scroll of modern California history. At one time, the sitting mayors of both San Francisco and Los Angeles were clients of Reilly.

He wasn’t flawless as an election strategist. Like any political operative, he had his share of defeats.

Reilly’s particular genius lay in the methodology — vertical integration — he brought to campaigns. Typically, one consultant would handle television advertising, another direct mail, another polling, another big-picture strategy, and so on.

“Everything was in-house with Clint and, at least in San Francisco, he was the first to do that,” said Jerry Roberts, who was a scruffy reporter for the city’s alt-weekly when he met a shaggy-haired Reilly more than 50 years ago. At the time, campaigns were a sideline for Reilly, who supported himself selling doodads and other salvaged wares in a movable flea market he operated on Fisherman’s Wharf.

“It was a smart business model,” said Roberts, who went on to lead two major California newspapers.

It made Reilly very rich.

In 1988, he managed what, at the time, was the most expensive political campaign in California history, a $64-million effort by the insurance industry to beat back a Ralph Nader-inspired reform initiative. Reilly lost, but his firm cleared at least $6 million on that contest alone — or about $17 million in today’s dollars.

“So that’s where our premiums went,” one guest observed with a low whistle as he arrived at the state-of-the art headquarters Reilly built not long after the Proposition 103 campaign. (Naturally, he threw an open house; for all his affluence, Reilly never did entirely shake the proletariat chip on his shoulder.)

A onetime seminarian — he left three years shy of being ordained a Catholic priest — Reilly was no saint.

He was hot-tempered, profane and egotistical. He embraced the nickname “Satan,” which a former client affixed after Reilly went to work for an archrival, as a reflection of his reputation for intimidation and mastery of the political dark arts.

In one fit of pique, Reilly took the unheard step of firing a client — Feinstein — via faxed press release because, he said, the former San Francisco mayor lacked the requisite fire to run for governor. The two eventually reconciled, though Feinstein stuck with members of the team that replaced Reilly and helped guide her to successive terms in the U.S. Senate.

If Reilly was at times overbearing — and known for being the kind of hellacious boss who gave employees night sweats — he was also generous and a genuine bleeding heart.

Before his career took off, Reilly volunteered for the United Farm Workers and lived an ascetic life, sheltering in church halls, as he ministered to the poor. Once he established his high-end consulting firm, Reilly retained his political staffers at no small expense, even during the lull between campaigns, rather than hiring and firing them as seasonal workers, which was the norm.

After leaving professional campaign consulting in the mid-1990s, and making a substantial fortune in real estate, Reilly gave prolifically to various charities and assorted civic caucuses. He started a charitable foundation of his own, Bay Scholars, which helps poor and underserved youth attend Catholic high schools throughout the area.

In 1987, when Reilly arguably resided at the height of his power and influence, he took on Pelosi as a client.

She was running for a rare open congressional seat in San Francisco and, though well known in political circles as a prodigious Democratic fundraiser and high-level activist, Pelosi was a blank slate to many voters. Reilly came up with a slogan that played on Pelosi’s Washington connections and many important friendships: “A voice that will be heard.”

More than that, he made a key tactical decision in the waning days of the campaign.

Pelosi was one of 14 candidates, several of them well-known Democratic officeholders. Ignoring Pelosi’s objections, Reilly sent out a mail piece to the city’s vastly outnumbered Republicans suggesting that a Democrat was bound to win the congressional seat and arguing that Pelosi was the best — or, at least, not the worst — of the bunch.

On election day, Pelosi lost the Democratic vote to Harry Britt, who succeeded Harvey Milk on the Board of Supervisors after Milk’s assassination. Still, Pelosi prevailed, by less than 4,000 votes out of nearly 108,000 cast. The winning margin was her Republican support.

The rest, as they say, is history.

Clint Reilly, a Bay Area milkman’s son who rose to manage the campaigns of California’s most influential political figures, has died at age 79.

A savvy political consultant, Reilly spearheaded early winning campaigns for some of the most recognizable names in California politics: former U.S. House Speaker Nancy Pelosi, Sen. Barbara Boxer and Sen. Dianne Feinstein.

Brandon Heist, Clint Reilly Organization’s head of business operations, said in a statement to The Times that Reilly died over the weekend in San Francisco. He died surrounded by family, which requested privacy. The San Francisco Examiner newspaper, which Reilly bought in 2020, earlier announced its owner’s death Sunday.

“I will always be grateful for Clint’s friendship and counsel over so many years,” Pelosi said in a statement. “As the manager of my first campaign for Congress in 1987, he brought his unmatched strategic mind to help create and amplify my slogan: A Voice That Will Be Heard.”

In a 1987 article, The Times attributed the success of Pelosi’s congressional bid to money — her campaign spent $1 million, more than her 13 opponents combined — and a sophisticated voter turnout program devised by Reilly. At the time, Pelosi was a 46-year-old mother of five children and a party activist known for raising large sums for Democratic candidates.

Reflecting on Pelosi’s rise last November, Reilly wrote in a San Francisco Examiner op-ed, “The mystery of being a political consultant is that you never know how your winning candidate’s career will turn out.”

Reilly’s legacy went beyond catapulting politicians into office.

He helped transform modern campaigning, said Oakland political consultant Jim Ross, who worked for Reilly throughout the ’90s, including on the election and reelection campaigns of San Francisco Mayor Frank Jordan.

In the ‘80s, Reilly was among the first consultants to merge grassroots organizing with new technology: using voter roll data to segment and target pivotal voters for turnout and persuasion, Ross said.

“It was a way to make sure that he spent resources effectively,” Ross said.

Reilly’s data-driven voter targeting tactics helped Feinstein, then-San Francisco mayor, beat a recall effort in 1983. They later had a public falling-out in 1989 during Feinstein’s failed campaign for governor.

Reilly’s portfolio wasn’t strictly Democratic. In 1993, he coordinated businessman Richard Riordan’s successful campaign for Los Angeles mayor by targeting homeowners’ anxieties about unemployment, crime and other symptoms of urban decay. When elected, Riordan became the first Republican mayor of Los Angeles in 36 years — and no Republican has been elected to that office since.

Reilly also advised the California insurance industry.

In 1988, he led the insurance industry’s losing $60-million initiative campaigns for Propositions 104 and 106. The pair of insurance industry-sponsored measures was designed to compete with Propositions 100 and 103, initiatives backed by trial lawyers and consumer advocates who wanted to reform the industry.

Voters ultimately passed Proposition 103, which promised insurance rate roll-backs and created the elected state insurance commissioner role. But Ross said it was one example of how Reilly would search for creative ways to achieve his client’s goals.

“Clint really pioneered in that election the idea of running competing ballot measures,” Ross said. “The reform measure was extraordinarily popular, it was going to pass, so instead of going at it directly, he ran a competing measure.”

A 1994 profile in The Times, from when Reilly was running Democrat Kathleen Brown’s bid for governor, described him as “one of the most powerful–and feared–political operatives in California.”

“When the opponent knows you have (him) on your side, a chill goes up their spine,” former San Francisco Mayor Frank Jordan told The Times. “He’s certainly better to have inside the tent than outside.”

Born in Oakland in 1947, Reilly was drawn to politics from an early age. He ran successfully for class president during fifth grade, with a campaign slogan his sister devised: “Take a Hint, Vote for Clint.”

Reilly’s relationship with Eugene Boyle, a Bay Area Catholic priest and liberal activist known for supporting the Civil Rights Movement, shaped his political views. He was passionate about supporting “the underdogs,” Ross said.

Reilly spent nine years in seminary before switching to pursue politics. His big break came in 1979, when he ran San Francisco Supervisor Quentin Kopp’s campaign for mayor. Kopp lost, but Reilly’s name stuck.

He soon developed a reputation for charging top dollar for his campaign strategy services and for his heavy campaign spending. In 1982, after Reilly brought Boxer to a decisive primary victory in her first congressional race, she fired him over excessive campaign spending, the Times reported in the 1994 profile.

As a boss, Reilly was “extraordinarily demanding,” Ross said, adding, “I reread pieces of direct mail five and six times now because of him.”

He also had a generous side, Ross said. Reilly spent time teaching young staffers the art of campaigning, a rarity in politics. Even after he left political consulting and shifted his focus to real estate, Reilly continued to help candidates with fundraising and messaging.

Reilly ran unsuccessfully for San Francisco mayor in 1999 and later turned his attention to local media and philanthropy, founding a nonprofit in 2008 to offer scholarships for low-income students to attend private college-preparatory high schools.

Reilly’s passing will not change the structure or current operations of the Clint Reilly Organization, Heist said. The organization’s media division includes the San Francisco Examiner — which Reilly acquired in 2020 alongside its now-defunct affiliate SF Weekly — and the Nob Hill Gazette, which he bought in 2016. The organization also has a hospitality company and real estate division.

“The organization’s commitment to its employees, partners, and the community remain firmly in place,” Heist said.

Condolences poured in from leaders across California on Monday.

Gov. Gavin Newsom and his wife Jennifer Siebel Newsom in a statement honored Reilly as a “San Francisco institution” with a brilliant mind and generous heart.

San Francisco Mayor Daniel Lurie said on social media the city “lost a civic leader who left a lasting mark on our city.”

Reilly is survived by his wife Janet and two daughters, Jill and Ava. Memorial arrangements will be announced later.

An informal advisor to Los Angeles Mayor Karen Bass handled communications for her office for free while simultaneously working on a three-year contract with Los Angeles World Airports worth nearly $600,000.

Yusef Robb, who runs the firm tk/Communications, was an unpaid spokesperson and advisor for Bass from February through the beginning of June.

On June 19, Robb began working for Lineage Logistics, whose cold food storage facility in Boyle Heights burned for more than a week last month. He continued to serve as an unpaid, unofficial advisor to the mayor, though no longer as a spokesperson, until The Times and other outlets reported on his work for Lineage on Saturday.

Robb said the airport contract was unrelated to his work for the mayor. But a legal expert said the arrangement raises questions about whether his free labor was a gift to the mayor and whether working for the city and private clients creates conflicts of interest.

“This was done through a transparent and public competitive bidding process,” Robb said in an email to The Times. “I provide communications support and training.”

The Bass administration said Robb’s unpaid assistance was “for the benefit of the city. It’s not a gift.”

In 2024, Robb signed the contract with Los Angeles World Airports, or LAWA — the city department that operates Los Angeles International Airport and the Van Nuys Airport — for $450,000 over three years.

He won the contract, which involved “executive media training” as well as “crisis communications,” over 10 other firms. It was updated in April to include additional work for $137,500.

A report from LAWA in support of the contract update said that “executive management at LAWA have benefited from successful, professional media training as well as support for LAWA crisis communications and response.”

Because tk/Communications has subcontracted to at least two other companies, Robb said his firm has earned no more than $315,000 over the three-year contract.

“There is no connection between the work Mr. Robb performs for LAWA and the assistance he provides for Mayor Bass’ Office,” said a spokesperson for Bass’ office. Bass is running for reelection against City Councilmember Nithya Raman.

The LAWA contract was Robb’s second with the city during the Bass administration. The city paid a total of $75,000 in 2022 and 2023 to Robb’s firm to provide “various communications services related to the start-up of the administration,” according to a contract.

Tk/Communications has worked for government agencies as well as political campaigns and private businesses, including the Los Angeles Department of Transportation, the Los Angeles Unified School District and the music and entertainment company AEG, according to the company’s website.

“We develop powerful narratives and engagement to accelerate and amplify our clients’ messages, whether they’re grounded in an investment proposal or a political campaign,” the website states. “We author and tell stories that build deep connections and lasting relationships that deliver more than you asked for.”

Robb has worked in and around City Hall for decades. He was a press aide in Mayor Jim Hahn’s administration, then worked for Eric Garcetti when Garcetti was a city council member and then mayor. He left Garcetti’s office in 2015.

Robb said he has provided “unpaid help to all sorts of people and businesses, to advance criminal justice reform, organize community movements, or just to find the right words.”

“I feel it’s important to help the city if I can,” he said.

Jessica Levinson, a professor at Loyola Law School and former president of the city’s Ethics Commission, said the airport contract shows how valuable Robb’s labor is, raising the question of whether he is providing a gift to Bass by working for her for free.

Another concern for the public, Levinson said, is that Robb is working for Bass at the same time that he has other clients and could potentially use his position at City Hall to advance those clients’ interests. His work for Bass could also make him more desirable for clients who believe he has the mayor’s ear, she said.

“What we’re worried about is undue influence, preferential access and backroom deals that benefit certain people, as opposed to the public,” said Levinson. “We don’t want public officials serving two masters.”

Still, Levinson said she does not believe that Bass has violated any laws by using Robb pro bono.

“This is an unusual setup,” she said. “That does not mean it’s illegal.”