Clint Reilly was the quintessential San Franciscan. For good and ill. 

Clinton Thomas Reilly was, in many ways, a quintessential San Franciscan. He was a wholly self-made man who ascended from poverty and despair to the heights of city society — but never lost the trappings of the milkman’s son he was. He put heaps of his own money into political races and charitable causes and raised even more. Many a local and national politician beat a path to the basement of Reilly’s restaurant, Credo, to swap stories with the man himself.

No longer: Reilly, the self-made mega-millionaire, groundbreaking political consultant, real estate baron, art collector, philanthropist and media tycoon, died over the weekend at age 79 of what sources describe as chronic lung disease. 

His story reads more like something out of San Francisco’s rough-hewn past than its anodyne present. 

Born in Oakland and raised in San Leandro, Reilly was the oldest of 10 children; his father was a milkman and his mother sold hot dogs at the ballpark. His beloved sister Jill died in adolescence and, barely a teenager, Reilly left home to join the seminary and study for the priesthood. 

He instead dropped out as a young man and slept in church rectories for years as he worked on programs for the poor. He volunteered for the United Farm Workers and traveled to Florida’s Dade County to combat bigoted anti-LGBTQ politicians as a straight ally when that was a truly dangerous thing to do. He operated a junk shop and ran political campaigns on the side. He became the state’s foremost political consultant, working to elect Nancy Pelosi, Dianne Feinstein, Barbara Boxer and many others — and parlayed his financial success into a real-estate empire. He ran for San Francisco mayor. He lost. He sued the Hearsts. He didn’t lose. He bought the former Hearst flagship, the San Francisco Examiner. He became, as friends and protégés echoed, consequential. 

Prior to events at the sumptuous Julia Morgan Ballroom, on the 15th floor of the Merchants Exchange Building, Reilly would drop in, unannounced, in a suit and sneakers and scare the bejesus out of the waitstaff with his mere presence. He skulked around like he owned the place. 

He did. 

Reilly got his start in politics in his mid-20s managing Dick Hongisto’s campaign for sheriff in 1971. He did this as something of a side gig while running a junk shop, where, in a truly 1970s detail, Reilly repurposed old milk cans into kitschy decor, and bought and sold used school desks. 

When Supervisor Quentin Kopp recruited Reilly to run his 1979 mayoral campaign against incumbent Dianne Feinstein, he did so at the insistence that Reilly get out of the used milk can business. “I hired him on the condition that he devote all his time to my campaign,” says Kopp, 97. “Which he agreed.” 

Reilly was busted for drunk driving while running Kopp’s campaign. Despite calls to fire Reilly, Kopp stuck with him. Reilly, by his own account, quit drinking in 1981 — and, adds Kopp, “once he stopped, you never had to worry about his advice.” 

Kopp, of course, lost to Feinstein — but it was closer than it could have been. For Reilly, the campaign punched his political ticket. And Feinstein definitely noticed: Four years later, in 1983, she hired Reilly to run her defense against a recall attempt. Reilly overperformed here: While Feinstein was a relatively popular mayor, a full 81 percent of city voters inveighed against the recall. The recall ended up making her stronger, and the same went for Reilly. 

He became a wealthy consultant, then a fabulously wealthy businessman and philanthropist and his consulting protégés are seeded throughout the political landscape; it harks to the Bill Walsh NFL Coaching Tree. 

“I answered a help wanted ad in the Chronicle in 1982. Clint hired me,” says Eric Jaye, one of the city’s most veteran political consultants. “There were three of us in that flat on Bush Street. When I left six or seven years later, there were 75 people working there. It was one of the largest political consulting firms in America.” 

Reilly ran bigger and bigger races and made more and more money. He raised eyebrows by courting incumbent Republican governor Pete Wilson and seeking to run his 1994 campaign before signing onto the campaign of Wilson’s opponent, Kathleen Brown. Reilly earned millions of dollars during the “insurance wars,” running ultimately losing campaigns on behalf of auto insurance companies in an electoral death match vs. trial lawyers. 

The fortune he walked away with seeded his foray into real estate. Employing the same skills he earlier demonstrated in buying and selling milk cans, Reilly gradually amassed a high-end real-estate portfolio.  

While Reilly left consulting in the 1990s, he was never far from politics. In 1999, he decided that, rather than run candidates for election, he’d do it himself. He challenged incumbent mayor Willie Brown, whom he condemned as the acme of corruption and cronyism. Despite spending a huge outlay of his personal fortune, Reilly received only 12.5 percent of the vote, and was personally tarnished by allegations of abysmal behavior during his drinking days. 

Reilly, always the master campaigner, had no answer here.

Reilly was a complicated man. He did not amass his great wealth and career success with anything resembling grace. He was a notably aggressive, political hard-charger in an era marked by them. He was a legendarily difficult boss. Even former employees with some fond recollections of Reilly say they wake up in the middle of the night, in a cold sweat, after nightmares that they were still working under him. 

The litany of alleged Reilly workplace misbehaviors former employees recounted to newspaper reporters resemble out-takes from the Kevin Spacey character in “Swimming with Sharks.” Reilly held his employees to high standards — often unfair and impossibly high standards. He did the same for himself.

“He worked people very hard and he, himself, would be working until 2, 3, 4 in the morning,” said political consultant Jim Stearns, who worked with Reilly and ran his 1999 San Francisco mayoral campaign. “It was quite a common occurrence to schedule a meeting for 5 p.m., be delayed until 10 p.m., finally sit down at 11 p.m. and then the meeting would go on for three or four hours. That was his style.” 

Reilly acknowledged his temper was a problem and expressed remorse for it in print. “There’s no excuse for” the anger so many colleagues recount, he told the Los Angeles Times in 1994. “I feel badly about it.” But anger, in Reilly’s profession, was something he couldn’t afford to do without. Candidates, he continued in the Times, “are not hiring me because they want me to get along with everybody. They’re hiring me because they want to win. The campaign is a war, you know?”

And Reilly won plenty of his wars. 

“He was beyond innovative. He was a pioneer,” says consultant Ace Smith, the go-to man for Gov. Gavin Newsom and Vice President Kamala Harris, who first met Reilly in 1979. 

“All these fancy national consultants used to meet with him and they were stunned about the way he was doing polling. Their idea of targeting was getting crude demographics from ZIP codes. Clint literally introduced the entire industry to what has become targeting and micro-targeting. He was the pioneer of that, full-stop.” 

To do this, Smith continued, Reilly “bought and owned one of the first VAX computers,” a closet-sized, 1970s mainframe. He amassed voter databases and rendered them searchable and sortable. With this sort of information — parsing constituencies on a granular level down to the “left-handed Lithuanians” — Reilly’s campaigns could communicate with voters far more efficiently. 

“You could be five or 10 times more efficient,” Smith continued. “If you use your budget like that, you can talk to the right voters five or 10 times when, previously, probably two times would be the best case.” 

This was, to adopt Joe Biden’s later phrasing, a big fucking deal. “A lot of people took Clint’s ideas,” says Smith, “and claimed them as their own.” 

Two years after losing the 1999 mayoral race, Reilly sought to rehabilitate his image. He provided unfettered access to SF Weekly for an in-depth profile. The resultant article was an exceedingly deep dive but, insofar as people remember it, they recall Reilly’s own mother, Bess, telling SF Weekly of her eldest child: “People do not really like him. He’s not lovable.” 

Oof. If Reilly hoped to once more take a crack at elected office, this was a devastating setback. In context, Bess Reilly’s statement made more sense: “Clint can’t tolerate petty people. He’s not into small talk. He’s not beholding. He pushes people; you know you have to.” 

But that quote provided a potential coup de grâce for any opposing political consultant with even a scintilla of Reilly’s talent; taking things out of context is a hallmark of political messaging. Reilly also told SF Weekly that modern political campaigns are intended to hook into people’s fears and prejudices, not their hopes. This, too, was deployed against him. 

So that was that. But voters and spinmeisters, in this case, didn’t have the only say. 

“I did love him,” said D.C.-based consultant and strategist Anthony Garrett, a former San Francisco politico. “He embraced me and was always extremely supportive. He saw talent in me. He was sort of like an older brother to me.” 

“I swam in the same waters as Clint. But we always knew he was special.”

What made Clinton Thomas Reilly tick? Both critics and allies alike point to a primary motivator: Respect. No matter how successful Reilly was, career-wise and materially, he seemed to always desire affirmation. 

“Clint has this Rodney Dangerfield problem, where he thinks somehow people don’t respect him,” consultant Bill Carrick told the Chronicle in 1999. “When Clint was an active political consultant, there was always this need to get an affirmation that he was good, talented, smart, on an equal plane not only with his peers in his [consulting] profession but also with the candidates themselves.” 

His friend and former employee Jaye says that, “Clint, from day one to his last day, always felt like he had something to prove.” 

It was, with a moment’s thought, a bit bizarre: Reilly seemed to desire the approval of people who hadn’t accomplished a fraction of what he had, and certainly hadn’t bootstrapped it with no help at all, as Reilly did. 

“He was keenly aware of class,” said Garrett. “He was keenly aware of what it means to not be treated the way someone wants to be treated and to want to be seen.”

Very few political thinkers may have been better than Reilly at sizing up the psychological pressure points of an opponent. It is not clear if he ever fully turned this skill inward.

In 1993, Reilly sued the Hearsts and then-Examiner executive editor Phil Bronstein following an altercation at the paper’s office. Just what the hell happened has never been definitively established, but Reilly left the building in an ambulance and required nine screws and a metal plate to repair his broken ankle. While the terms of the settlement have never been made public, Reilly told SF Weekly that he bagged $600,000. 

In 2000, he sued the Hearsts again, attempting to block the Examiner’s purchase of the Chronicle. That plan ultimately came to pass — but Reilly’s suit revealed that Hearst executives and Mayor Willie Brown discussed favorable coverage of the mayor in return for Brown’s support of the newspaper merger (the Hearst Examiner, surprise, surprise, surprise, endorsed Brown for mayor in 1999). That was a salient detail for the public to know — and the $2 million Judge Vaughn Walker awarded to Reilly didn’t hurt a bit. 

In 2020, Reilly bought the Examiner. Considering his history with the Hearsts, it was mind-boggling that he’d end up owning the paper. His purchase likely saved the erstwhile “Monarch of the Dailies” from oblivion. 

But Reilly had the bad fortune that the San Francisco Standard, funded by an even wealthier San Francisco politico, Michael Moritz, emerged not long thereafter. It soon filled the niche the Examiner could have if it was willing to pay top dollar for journalism, as the Standard does, and take on establishment figures Reilly considered friends, as the Standard does. 

SF Weekly was a sister paper of the Examiner and Reilly made the decision in 2021 to shutter the Weekly to devote more resources to the Ex. Despite promises to preserve SF Weekly’s archive, the exact opposite transpired. You cannot find the 2001 SF Weekly profile of Reilly on the SF Weekly site (author Peter Byrne put it on his own site). You cannot easily find any of the articles, from any of the publications he owned, recounting the era when Clint Reilly was a primary mover and shaker in this town.

But he was.

“He was equal parts tenacious, terrifying and inspiring,” says one former employee. “He was a civic force.”  

“He believed politics could change people’s lives,” said Jaye. “He took it seriously. Politics, to many people who practice it, is a game or a grift; it’s what you do until it’s socially acceptable to hit the bars. Not Clint.”