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The Power and the Story

How Willie Brown continues to control his own narrative.


When things go well for Willie L. Brown Jr., no one’s the wiser. Advice is requested, wisdom is dispersed, phones are dialed, and appreciable sums of money change hands—all out of view of the public. Such transactions often turn out profitably for Brown, padding the considerable wealth he’s accrued since departing elected office in 2004 and solidifying his stature as the city’s ultimate fixer. But sometimes, despite the most well-greased skids, things can go off the rails.

It was such a derailment that brought Brown—the former San Francisco mayor and state assembly Speaker and current influence peddler, municipal elder statesman, and freelance San Francisco Chronicle columnist—to a spacious Embarcadero Center boardroom one immaculate morning this April. Just before 10 a.m., Brown sauntered into the room, sitting down with his back to a bank of oversize windows that framed Coit Tower in front of a cloudless pale-blue sky. Brown, wearing a magisterial dark suit and red tie, sat to the left of his legal counsel, Timothy Flaherty, and across the table from Dan Berko, the attorney for onetime Brown ally Joe O’Donoghue, the man who was both suing and being sued by the former mayor.

“Good morning, Mayor Brown,” said Berko. “Have you ever had your deposition taken before?” The question, the attorney knew, was ludicrous, akin to asking a rodeo clown if he’d ever been pursued by a bull. “Oh, I have no idea how many times,” Brown responded. “I’m 82 years old, and I’ve been practicing law for almost 60 years, and I’ve been in and out of matters involving taking of depositions.”

Willie Brown with one of the highranking officials on his speed dial.

Photo: Randy Brooke/WireImage/Getty Images

Brown’s facial expression in this moment seemed to convey a singular, stern message: Fool, don’t waste my time. But over the next seven hours and change, that message would be ignored by the counsel for O’Donoghue, 78, the retired chieftain of the Residential Builders Association and, in an earlier era, one of the city’s premier bundlers of political cash. Throughout the 1990s and into the ’00s, O’Donoghue was tapped by Brown to direct political donations toward whatever candidate or cause the mayor desired. Together, they made—and unmade—political careers, rewrote the rules, and helped transform SoMa into a realm of office towers and live-work lofts. But that was then: Brown and O’Donoghue’s partnership has since gone sideways. At issue this April morning is a $10 million 2005 real estate investment that has soured, with O’Donoghue and Brown each accusing the other of reneging on agreements following their group’s purchase of an art deco lakeside residential tower in Oakland.

O’Donoghue accuses Brown—who has moved his wife, Blanche, and two adult daughters into the building and, by Brown’s count, sunk some $600,000 into upgrading their units—of operating with impunity on the site without his partners’ consent and impeding the construction of a condo tower on open space at the rear of the property. Brown, under Berko’s questioning, said that his wife was entitled to live in the building “cost-free,” an arrangement never codified in writing with his fellow investors: “These were all a group of friends,” Brown explained. “Each of us was trustworthy.” Brown and his wife, in turn, last year filed suit against O’Donoghue for changing the locks on Blanche’s storage unit and purportedly berating her in an incident that Brown’s lawyers portrayed as “elder abuse.”

The particulars of the suits and countersuits and the corresponding deterioration of a web of friendships and allegiances are cumbersome to parse. But O’Donoghue’s motives are not. The retired builder and bundler possesses an appetite for retribution straight out of a Mario Puzo novel; his sense of outrage, at this point, cannot be slaked by any offers of a settlement—which Brown’s attorneys have offered, and which O’Donoghue says he’ll never accept. “We will, if necessary, bury Willie Brown,” he tells San Francisco. Brown, who declined multiple interview requests for this story, doesn’t appear to be overly concerned about O’Donoghue’s threats.

Again and again during the daylong deposition, the former mayor bobbed and weaved, dismissing Berko as “not sharp enough” to ask the right questions, or offering beguiling responses to questions that were perhaps righter than he wished them to be. “You want a different answer,” Brown said in response to a series of queries about Blanche Brown’s living arrangements. “You can’t get it from me.” At other times, his answers betrayed truths that were as familiar to longtime Brown watchers as they were enraging to his inquisitors. Asked why he alone was entitled to house his relatives cost-free in spectacularly valuable units despite the same $2 million buy-in as other partners in the investment, Brown calmly replied that it was because he was “a desirable investor.” Why was he so desirable? “Because of who I am.” 

This has become something of an MO for Brown: I do it because I can, and I can because of who I am. A dozen years out of elected office and at an age when most ex-politicians are lingering over their morning bowls of Wheatena before a round of golf, Brown remains a busy man, and a much sought one. “You can get a permit for a high-rise faster than you can for an addition to your home—if you can afford to pay for expediters,” explains a city developer. It’s hard to conceive of a more connected expediter than Da Mayor. 

Even at 82, his friends and foes alike will tell you, Willie Brown is a formidable player in San Francisco—the smartest man in the room, regardless of the room. And, in some respects, his influence has only grown over time. Two decades ago, the San Francisco Chronicle produced a series of articles titled “Willie Brown, Inc.,” spotlighting then-mayor Brown’s feat of salting the public payroll with hundreds of his political minions and thousands of additional city employees. Today, Brown, a marquee writer for the same paper, can place calls to that “patronage army” from his waterfront law office, which is, unsubtly, christened Willie Brown, Inc. Though his official capacity (is he a lawyer? a lobbyist? a kibitzer? a consultant?) is not always well defined, his brand remains undiminished. 

“The difference between him and most lobbyists in this town,” says a longtime political operative, “is it’s not all about the money for him. For him, it’s about staying in the game.” Not that there aren’t piles of money at stake, or that Brown isn’t skilled at maximizing his haul of it. It’s that the money, in Willie’s World, is an ancillary benefit; his genius has been to monetize what he’d be doing all day long anyway—placing call after call, dispensing and receiving intelligence, and living the unapologetic life of a palace whisperer, high roller, and bon vivant. In this way, says the operative, Brown’s a bit like ageless quarterback Tom Brady, who has stated a desire to play football in perpetuity, long after all of his contemporaries have broken down. But “in football,” this insider continues, “there are physical limitations. In politics there are none.”

Willie Brown can stay in the game until his dying day. And he will. Unless somebody manages to bury him first.


Willie Lewis Brown Jr. was born in 1934 in segregated Mineola, Texas, where he grew up fishing coins out of spittoons after shining the horseshit-encrusted boots of the town’s white elites. He worked his way through UC Hastings law school by sweeping up the place after hours. Later he carved out a niche as the lawyer to call if you were a San Francisco pimp, junkie, dealer, or prostitute. After that, it was on to politics, and you know the rest: 30 years in the state assembly, the last 15 as Speaker; elected and reelected mayor in 1995 and 1999; succeeded by protégés Gavin Newsom and Ed Lee; now paid handsomely as a lawyer, lobbyist, and ersatz film critic (Furious 7, he opined, has “no real story and no real acting, but the stunts are unbelievable”). This is Willie Brown’s version of the American dream.

And, like a dream, Brown’s role in the inner workings of the city remains highly mysterious. Even to the sharpies hired to shepherd multimillion- or even multibillion-dollar projects through San Francisco’s arcane development process, it’s not always clear if they’re working with or against Willie Brown. It’s a bit like holding a naval battle in a dense fog: “Half the time,” says a development strategist, “you don’t even know if he’s involved. You hear it through the conversations. But you never really know.”

Even when you do know, Brown’s services—for which past clients say he can command $10,000, $25,000, $50,000, or many times more—remain opaque. Take the following interaction, as relayed by a prominent San Francisco developer whom we will call Smith (like most people interviewed for this story, Smith preferred to remain anonymous so as not to alienate Brown): Smith and Brown meet over a couple of drinks at the Palace. (Did Smith pay for said drinks? “Of course!” he says.) Smith explains what he’d like to build; Brown explains whom he’ll have to talk to and offers to phone one or two of the proper city officials so Smith’s calls “will be returned.” The drinking and talking clock in at perhaps an hour, definitely less than two; Smith and Brown exchange no paperwork and sign no contracts. It’s “just a handshake, and give me a check,” says Smith—a check with four zeros on it. “It’s a fairly exorbitant consulting arrangement,” concludes Smith. “He doesn’t do that much.” In this case, he says, Brown “was able to put us in touch with the right people, but we still had to do all the work.”

No matter—Brown’s client list remains stacked. While his docket is a closely guarded secret—and relationships like the one recounted above do not generate written records—paper trails indicate that Brown has worked on behalf of such big hitters as AnsaldoBreda, makers of the city’s clunky light-rail vehicles (purchased during Brown’s mayoral terms); development giants Catellus and Lennar (which, interestingly, jousted over the lucrative Concord Naval Weapons Station project); downtown staples Recology and PG&E; and a slew of high-rise developers.

When entire teams of movers and shakers realize they’ve “hit the ceiling on what the group can do,” one political strategist says, someone will acknowledge, “That’s a Willie job.” Brown is brilliant, and Brown is a lawyer, but these are not jobs requiring a brilliant lawyer. “He’s certainly not writing legal briefs,” notes a former Brown underling. “He does what [former New York senator] Al D’Amato does: He picks up the phone.”

Of course, there have been instances when Brown’s involvement in a deal sees the harsh light of day and fallout ensues (but, in typical Brown fashion, never for him). In 2013, after developer David Choo’s business imploded, bankruptcy filings revealed that he owed Brown $750,000 in lobbying fees. (Brown, who was not a registered lobbyist at the time, faced no blowback, legal or otherwise.) Last year, the Wall Street Journal published emails between would-be governor Steve Westly and alleged woman-beating tech CEO Gurbaksh Chahal indicating Brown had asked for $1 million to intervene in Chahal’s domestic violence case, in which he was accused of striking a female companion more than 100 times (see "How Da Mayor Makes Da Money").

Despite his unseemlier associations, it’s still difficult to think of anyone in the state who won’t accept a call from Willie Brown. “He’s able to open doors and put meetings together—with people it’s sometimes difficult to get meetings with,” says a developer who has paid Brown hundreds of thousands of dollars for multiple engagements. Brown, he says, doesn’t make any promises about what he can and cannot do—or even what he will do for a client. He merely agrees to “attempt to set up meetings and get us access.” Brown, in this role, is strictly a “facilitator,” not a “negotiator.” He is hired and compensated for his “gold-plated Rolodex.”

That Rolodex, and the years of next-level machinations required to compile it, mean that Brown still has valuable “midlevel relationships in the departments.” His work can be undertaken on the staff level well before any piece of legislation finds its way to an elected official. 

You can, in fact, still find Brown’s allies—and appointments—speckling the city’s money commissions: His former chief of staff Eleanor Johns, who now heads the Willie L. Brown Institute, has been on the Airport Commission since Brown put her there in 2003 (Brown appointees, in fact, make up a majority of this commission); Ann Moller Caen still sits on the PUC Commission; Kimberly Brandon still serves on the Port Commission. 

The list of city higher-ups who came up under Brown is formidable: mayoral chief of staff Steve Kawa; Public Utilities Commission head Harlan Kelly; City Administrator Naomi Kelly; Controller Ben Rosenfield; former Transbay Joint Powers Authority executive director Maria Ayerdi-Kaplan; Human Services Agency boss Trent Rhorer; Public Works head Mohammed Nuru; and—of course—Mayor Ed Lee.

As has been the case for decades, any politician receiving a call from Brown knows he or she is speaking with someone who can, without leaving his table at Le Central, marshal piles of cash either for or against them. Amassing money and directing it to a designated cause is one of Brown’s raisons d’être. Years ago, O’Donoghue recalls, Brown instructed him to bundle funds for Governor Gray Davis (O’Donoghue raised $100,000) and, not long after that, to direct cash to Arnold Schwarzenegger—the man who would go on to unseat Davis. O’Donoghue says he did this unquestioningly, earning sway for both himself and Brown. “Willie never benefits financially from donations. That I can say emphatically,” O’Donoghue says. “What he got is access. That’s more important than a cut.”

Access begets access, and few have more of it than Brown. His ability to chat up high-level officials—who often owe him their careers—is unrivaled by that of anyone in state or city government. And his ability to turn around and disseminate the lowdown to his clients makes him invaluable to those who can afford him. Conveying raw information from the highest rungs of power, says a city consultant, “is a pretty big, fat deliverable.”


There have been Willie Brown types before. (White House counsel and D.C. honcho Clark Clifford purportedly charged tens of thousands of dollars for a single phone call, too.) But there has never been another power broker with Brown’s combination of smarts, moxie, flash, and perceived invincibility; he is all but certainly the most investigated least prosecuted politician this state has yet produced. (Asked in his April deposition if he keeps notes of “important agreements that you reach,” Brown answered unequivocally, “I do not”—unsurprising for a man who likes to quip that the e in “email” stands for “evidence.”)

And yet, getting into bed with Brown carries its own risks, the greatest of which is the sinking suspicion that you may be getting played. Sure, hiring Brown requires a bucket of money, reasons a city development consultant, but “if you’re working on a project that costs 100 buckets of money, who would you hire?” Willie Brown, he says, “is the Toys ‘R’ Us of political strategists. He is the category killer.” If Brown’s gold-plated Rolodex shaves a few months off a project’s timeline, then he’s paid for himself many times over. “You got a house?” barks a veteran San Francisco politician. “You got fire insurance? You think your house is going to catch fire? Or is it just a prudent thing to get insurance?”

Willie Brown, then, is the Cadillac insurance policy that a CEO can’t afford not to purchase. It’s not unlike hiring Rem Koolhaas to design your building, or bringing in Goldman Sachs to structure your firm’s merger. If things go poorly, that CEO can always say, “Don’t blame me. I hired the best.” That’s not to say that Brown’s asking price doesn’t make some customers queasy. A city politician recalls witnessing more than one favor seeker recoil in horror when hearing the cost of Brown’s services: “Jesus Christ! Fifty thousand bucks to make one call!” But, longtime associates say, Brown is not unbendable when it comes to his fee: It all depends on how much your cause interests him and, crucially, how much he thinks you can pay. (He’s also been known to raise scads of cash, for free, for favored charitable causes.)

“I think,” concludes a longtime city politician, “that Willie is just a fucking hustler.” Brown has admitted as much in print: In one of his more infamous Chronicle columns (an effort that the paper’s editorial page editor, John Diaz, deemed “absurd” on Twitter), Brown wrote that the disgraced former state senator Leland Yee, who had copped to federal corruption charges, was guilty only of “thinking he could hustle some money, that he was ripping off someone who was not very smart.” Yee’s greatest crime, in Brown’s estimation, wasn’t violating the public trust or engaging in criminal pay-to-play—it was not thinking big enough. Along similar lines, Brown’s rationale for opening a file on the Chahal case, as explained in a follow-up, make-good Chronicle story, was, essentially, that someone with more dollars than sense had offered him a fortune. 

Brown, his former colleague concludes, has established a cottage industry by exploiting the theory of the greater fool. That is, the price of his services is determined not by their actual value, but by the irrational expectations of those bidding on them: “He is finding a sucker to pay him,” says the politician. This is a specialized line of work, and not exactly the sort of thing you can advertise in the local paper.

Or can you?


Brown’s ally-turned-opponent Joe O’Donoghue claims that a few years ago, the city’s best-dressed man told him, “Joe! I’m broke.” O’Donoghue intimates that if he had Brown’s personal life—a wife; a longtime companion, Sonya Molodetskaya, with a fashion fetish and a Brown-funded FiDi loft; three grown children; four grandchildren; a teenage daughter borne by his former City Hall fundraiser; and, all around, one of this city’s most jammed social calendars—he’d be broke, too. “He has the zest for life,” says O’Donoghue, a teetotaler. “He is suave and smooth and also as hard as a goddamn rock.”

Brown, per longtime friends and associates, has a “lifestyle that requires a lotta money” and “a high burn rate”; he needs to “make as much money as he can for his kids and grandkids.” One of the best ways to keep the till ringing is to put his name in the news and his services at the forefront of his clientele’s mind. And the easiest way to do this, for Brown, is to write in the newspaper about his ingenious exploits and access to powerful people. Willie’s World, a breezy column that has run Sundays in the Chronicle since 2008, is the finest advertising for Brown’s services that money can buy—and, in fact, they pay him for it. “If he didn’t have that column,” assesses a fellow city politician, “he’d be at home under the covers under heavy sedation. That column keeps him front and center. It keeps him”—and here the air quotes come out—“in the game.” 

So important is the Chronicle column to Brown that he was allegedly willing to sacrifice wildly lucrative business opportunities to keep it. In early 2015, Brown and retired UCSF chancellor Bruce Spaulding—two of the prime movers behind the metamorphosis of Mission Bay from a toxic, abandoned rail depot into a biotech office park—met with the hard-charging public relations guru Sam Singer over drinks at the Palace. The venture in question involved a well-heeled, free-spending consortium calling itself the Mission Bay Alliance, which was dead set on killing the proposed Golden State Warriors arena on Third and South Streets. Brown had previously worked on the Warriors’ side, when the team wanted to build a stadium on Piers 30–32—but now he had switched jerseys, throwing in to be the alliance’s chief political strategist. He and Spaulding wanted to know if Singer would be interested in serving as the group’s spokesman. “Hell yes,” Singer recalls saying. “Count me in.”

Weeks later, Brown and Singer had a different sort of interaction. “Willie told me that he’d had a conversation with the Chronicle,” Singer recalls. “They said, ‘You have a choice: You can continue as a columnist or you can take this gig.’ He enjoys being a columnist. He gave up this gig.” Chronicle editor-in-chief Audrey Cooper declined to answer whether the paper offered Brown an ultimatum regarding his work against the Warriors arena. She also would not clarify whether Brown provides the paper with a list of current and former clients—something that would allow his editors to prevent obvious conflicts of interest from appearing in Willie’s World. “I’m very comfortable that we have done right by our readers with Willie’s column,” she wrote, “which is both enlightening and entertaining.” (Why the Chronicle would specifically take umbrage at Brown’s work with the Mission Bay Alliance, while allowing him to hype other clients and savage his opponents in print, is a subject of some conjecture around town. Nobody seemed to mind Brown working toward an arena on Piers 30–32.)

In the meantime, Brown can columnize about instituting transit policies that would, nakedly, benefit his rideshare-app client or promote his political creation Gavin Newsom as a potential Hillary Clinton running mate. (Perhaps coincidentally, Lieutenant Governor Newsom has pushed a San Bernardino County plan to allow the use of eminent domain to seize homeowners’ underwater mortgages—a plan that would enrich a company in which Brown is a partner. In private, and when not writing for the newspaper of record, confidants say Brown is far less charitable regarding Newsom’s abilities.)

In any case, Brown’s long-running column has, for many veteran Chronicle staffers, been a bitter pill to swallow. Brown, like his friend and Chronicle predecessor Herb Caen, is a dandy, a raconteur, and an omnipresent city fixture. Both have been accused of using their positions for personal gain. But Caen wasn’t a registered (or unregistered) lobbyist, and he didn’t have a habit of eluding Chron reporters’ calls Monday through Saturday before having his own say on Sunday. Especially for reporters with institutional memories of the “Willie Brown, Inc.” series, this remains the great shame of the newsroom. “Willie Brown is a pox on all of us,” says a former Chron reporter. The advent of his column “was a devastating blow to whatever serious work people thought they could do at the Chronicle.” The indignity of this situation, the reporter continues, has been epitomized by instances of Brown literally phoning in his column to fellow Chronicle scribe Phil Matier and “wordsmithing it. Loudly.” Transcribing Matier and Brown’s mealtime conversations in order for Matier to write Brown’s column is a duty assigned to a low-level newspaper staffer.

Asked by Berko in April what he does for a living, Brown replied, “I’m a lawyer,” then quickly added, “I’m a columnist.” Queried whether he considers himself a journalist, Brown said no. “So,” continued Berko, “you’re kind of like Rush Limbaugh?” Brown was unamused: “Don’t burden me with that hefty obligation.”

“When I went
to work for Willie,” recalls a former aide, “I thought, ‘This is the smartest person I’ve ever met.’ But”—he pauses—“I changed my mind.”

Brown was—and is—great at what he does. Yet, says the former underling, “I felt his interests and instincts and perception and skills were in a narrow area.” Brown is unquestionably one of the most talented politicians this city has ever spawned. With an unmatched ability to network and cut deals and feed his army, he got things done here: City Hall bedecked beautifully in real gold, SoMa resurrected with condos and lofts, Mission Bay remade into a biotech hub, a new baseball stadium that’s the envy of cities across the country. The list goes on. But “the aspects of government that didn’t interest him—Muni, public education, homelessness—he let them run their course.”

Seen cynically, one could say that there’s an upside to leaving behind so much dysfunction. After all, who benefits more from broken systems than a fixer? Brown has, over the past 60 years, so mastered this city’s game that he and San Francisco are increasingly difficult to tell apart: Both are flashy and unapologetic, on the make, unbound by rules, ingenious, self-congratulatory, vain, unseemly, and prone to booms and busts. And, until proven otherwise, indestructible.

The April deposition of Willie L. Brown Jr. lasted from 10 a.m. until after 5 in the evening. The octogenarian Brown did not ask for any breaks. He did not even ask to adjourn for lunch. “He’s a tough old cougar,” concedes his interlocutor Berko. The dialogue between the two, reconstituted in 280 pages of transcription, winds about like a verbal Möbius strip—it continues on, seemingly infinitely, but never advances. Brown, toward the end, grew weary of this dynamic. “That’s all I’m going to say, Mr. Berko,” he concluded in the waning moments of a very long day. “And I’m going to leave if you keep asking the question. Because you’re wasting my time.” 

Shortly after the deposition concluded, Brown was scheduled to conduct some business via a conference call. He dialed up right there in the lobby. Time, after all, is money.

Originally published in the June issue of San Francisco

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