In November 2016, California’s Proposition 64, a measure to legalize the adult use of cannabis, looked to be cruising to victory. The initiative, led by then-Lt. Gov. Gavin Newsom, attracted few high-profile opponents—with one notable exception.

San Francisco created the modern medical marijuana movement. So why is the city's iconic leader California's last drug warrior?

Sen. Dianne Feinstein, California’s powerful US Senator, high-ranking Democrat, and revered San Francisco icon, blasted the measure early and remained an unrelenting opponent. She signed a ballot statement accusing cannabis companies of plotting to lure “millions of children and teenage viewers” with television ads.

The Prop. 64 campaign spokesman called the statement “reminiscent of the ‘reefer madness’-style disinformation campaigns that subverted honest dialogue around this issue for decades.”

Feinstein’s opposition was hardly a surprise. For decades, the San Francisco Democrat has opposed nearly all forms of drug reform, from medical marijuana in the 1990s to California’s adult use measure in 2016. In recent years she’s been a key ally of Iowa’s Republican Sen. Charles Grassley, the two elder senators working together to block Congressional measures aimed at drug reform in the age of medical and adult-use legalization.

In 2015, the Feinstein-Grassley tandem warned that America was losing its will on drug enforcement as new states legalized cannabis for recreational or medical use. “We’re already seeing signs that the United States’ position on drug control issues is weakening,” Feinstein and Grassley wrote in a letter to then-Attorney General Eric Holder.

SF’s Dianne Feinstein: ‘Worst Senator on Marijuana Reform’ | Chem Tales | San Francisco http://t.co/wom3dRsGiE

— Farrell Hamann (@farrellhamann) July 27, 2015

Many national observers on cannabis policy remain perplexed by Feinstein’s unchangeable position. For decades, San Francisco’s iron lady has stood against her city and state’s famously tolerant views on marijuana.

To many of her constituents, though, Feinstein’s anti-reform position has long been accepted as an odd curiosity, a minor disagreement on a low-priority issue. But lately it’s become something more. With California’s adult-use cannabis industry set to open in three months, the 84-year-old politician’s intransigence is now seen as a potential vulnerability—a symbol of a Senator and her state moving in opposite directions.

Feinstein's prohibitionist stance may finally catch up to her in 2018.

D ianne

Feinstein emerged from the same traumatic era in San Francisco as Dr. Donald Abrams, one of the world’s most renowned medical cannabis researchers.

Both were shaped by the city by the bay, and helped transform it as front-line protagonists who rose to face the challenges of the AIDS epidemic in the 1980s and 1990s.

Abrams treated AIDS patients at San Francisco General Hospital and became a leading researcher in identifying the human immunodeficiency virus, or HIV. Feinstein rallied logistical efforts to expand medical care for patients and, for a time, her administration allocated more money for AIDS response in San Francisco than the federal government did for the entire nation.

What was once prized as Feinstein's old-fashioned common sense now risks being seen as just old-fashioned—and out of step with California voters.

But by March 2012, Abrams and Feinstein traveled in decidedly different circles on cannabis policy. At a reception for the Senator at the French Tudor estate of political strategist and former Democratic Assemblyman Rusty Areias, Abrams attended as the guest of a Feinstein donor. He wasn’t there to wax nostalgic. Abrams and a cadre of cannabis activists hoped to buttonhole Feinstein about medical marijuana. They hoped to convince her to back off on prohibitionist policies that kept alive the threat of DEA agents raiding medical marijuana dispensaries and gardens.

Michael Backes, a partner in marijuana dispensaries in Los Angeles and Sacramento, was standing nearby as Abrams alone approached Feinstein not long after she arrived.

“Donald took Feinstein to task quickly and expertly for her rigid opposition to the medical use of cannabis,” said Backes, author of the medical marijuana guidebook, Cannabis Pharmacy. “She gave him the micro-stump speech to justify her stance. Abrams wasn’t having it and insisted she look at the evidence.”

Backes said the senator stiffened and turned to walk away. Fred Gardner, editor of the cannabis journal O’Shaughnessy’s who wrote about the exchange based on an account from Abrams, said Feinstein waved her hand to signal the conversation was over.

“Well,” Feinstein said, “we will just have to agree to disagree.”

Steve DeAngelo, co-founder of Oakland’s Harborside Health dispensary, also attended the event. He took offense as the Senator began her remarks to the crowd by poking fun at the doctor who had challenged her on the science of medical marijuana. (Feinstein’s office declined an interview request.)

“This was the number one researcher in double blind cannabis trials,” DeAngelo fumed. “And she was openly contemptuous.”

Shaped by San Francisco

To many in California, Dianne Feinstein will always be the face of calm and courage amid unspeakable tragedy.

In November, 1978, she was the president of the San Francisco Board of Supervisors when Dan White, an ex-firefighter and cop, quit the board in a huff over clashes with Harvey Milk and other supervisors. Later he wanted his job back.

Feinstein saw White walk past her office and called out to him. Mayor George Moscone was going to appoint someone else to the seat and it was up to her to let him know. But White headed away. She didn’t know he already gunned down Milk and the mayor.

Soon Feinstein went to Milk’s office and saw her fallen colleague. She grabbed Milk’s wrist to feel for a pulse. Her finger slid into a bullet wound.

Later, her clothing spotted with blood, Feinstein faced television cameras in the City Hall rotunda.

“As president of the Board of Supervisors,” she said, in a voice anguished but unbreaking, “it is my duty to make this announcement: Both Mayor Moscone and Supervisor Harvey Milk have been shot and killed.” There were gasps and screams. She paused and went on: “The suspect is Supervisor Dan White.”

“It was the defining moment in her political career,” said Bob Shrum, director of the Jesse M. Unruh Institute of Politics at the University of Southern California. “She took a terrible tragedy and handled it effectively and with empathy. Without that moment, I’m not sure she would be where she is today.”

Feinstein succeeded Moscone as mayor and ended the 1980s with a reputation as one of the nation’s most effective city leaders. The video footage from 1978 would be used in a 1990 Feinstein gubernatorial campaign commercial that emphasized her role in guiding San Francisco back from the horrible event. She lost to Republican Pete Wilson but was elected two years later to Wilson’s open seat in the U.S. Senate.

'Dianne was, and is, always will be pro-police. It is said that Dianne never met a uniform she didn’t like.' Jerry Roberts, Feinstein biographer

John Lovell, a powerful Sacramento capitol lobbyist for police organizations including the California Narcotics Officers Association, says he wonders if the tragedy cemented Feinstein’s resolve as a tough-on-crime politician. He says she is “easily the most law enforcement-supportive member of the United States Senate.”

“She dealt with a double homicide up close and in-person,” Lovell said. “Crime is not abstract at that point. It’s not a question for a sociological discussion. Two people in professional lives were snuffed out. Those are searing moments.”

Early Influence: Parole Board Experience

Feinstein’s opposition to marijuana reform was set early. A few years ago she told an Associated Press reporter that while serving on the state parole board for women in the 1960s, she saw too many criminals who “began with marijuana and went on to hard drugs.”

Jerry Roberts, former managing editor of the San Francisco Chronicle and author of an unauthorized 1994 biography, Dianne Feinstein: Never Let Them See You Cry, said Feinstein seemed uncomfortable with cannabis on a visceral level. Though she came of age politically in the era of Haight-Ashbury hippies, Roberts said, Feinstein neither cared for the Summer of Love nor the smoke wafting from Golden Gate Park.

“It is culturally foreign to her,” Roberts told me recently. “She was always opposed to it. And Dianne was, and is, always will be pro-police. It is said that Dianne never met a uniform she didn’t like. And I don’t think this [cannabis reform] is anything she has ever felt any compelling reason to revisit.”

A City Changed, a Leader Did Not

Few American politicians have had more opportunity to revisit the issue. California’s medical marijuana movement was born in the 1980s in the city she led. As the AIDS crisis devastated San Francisco, many patients discovered cannabis as a healing medicine. Those fighting Kaposi’s sarcoma, a deadly cancer associated with AIDS, used cannabis to tamp down the nausea caused by chemotherapy. Others fighting AIDS wasting syndrome relied on it to stimulate their appetites. Mary Jane Rathbun, aka “Brownie Mary,” became a local folk hero by offering cannabis-infused brownies to AIDS patients at San Francisco General Hospital.

In 1991, Dennis Peron and other activists led a campaign to pass Proposition P, which made medical marijuana legal within the city limits. For years, Peron had been providing cannabis to patients out of his house in San Francisco’s Castro neighborhood.

San Francisco’s experience with medical marijuana led to California’s Proposition 215, a statewide version of the city measure. As most voters in her home city came to embrace—or at least allow—medical marijuana, Feinstein’s opposition only hardened.

During the 1996 campaign, when Feinstein served as California’s senior US Senator, she loudly and publicly opposed Prop. 215. Feinstein joined law enforcement groups in arguing that the initiative was a ruse for legalizing pot. “You’ll be able to drive a truckload of marijuana through the holes in it,” she declared.

As polls showed her constituents as souring on the War on Drugs, Feinstein resisted nearly every effort to dismantle it.

Even as polls showed her constituents as souring on the War on Drugs, Feinstein has resisted nearly every effort to dismantle it. In 2008, she led the opposition to defeat Proposition 5, a statewide initiative that would have expanded treatment programs, in lieu of prison, for drug crimes.

Two years later she served as the chairwoman of the campaign to defeat California’s Proposition 19, which would have legalized cannabis for adult use.

In 2014, Feinstein campaigned against weakening a mandatory 25-years-to-life “Three Strikes” sentencing law and fought a successful initiative, Proposition 47, that reduced many non-violent felonies to misdemeanors.

Dennis Peron, who’s been battling Feinstein over cannabis issue since the 1970s, doesn’t see her changing anytime soon. “She ran against it” decades ago, he said, “and has been opposing marijuana for a generation.”

A Moderate ‘San Francisco Liberal’

Though conservatives in the rest of the country love to mock “San Francisco liberals,” Dianne Feinstein has been revered—and re-elected—for a quarter-century precisely because she’s not an extreme liberal. Feinstein has always been an old-school Democratic centrist: Pro-police, pro-environment, and anti-drugs. California voters perceived her, perhaps above all else, as a moderate who offered competence and the ability to get things done.

Feinstein survived and thrived as a moderate Democrat – pro-police, pro-environment, anti-drug – in a politically diverse state.

In recent months, though, Californians have seen growing signs that Feinstein may face a challenge from the left if she seeks a sixth Senate term in 2018. What was once prized as old-fashioned common sense now risks being seen as just old-fashioned—and out of step with the state’s voters.

Despite her age, she remains tough to beat, with the state’s open primary system seen as diluting potential Democratic opposition. But her prospects for a smooth run may have ended after recent conciliatory remarks about Donald Trump.

During an event at San Francisco’s Commonwealth Club on Aug. 29, Feinstein said of Trump: “I just hope he has the ability to learn and change. And if he does, he can be a good president.”

The crowd responded with boos.

Senate leader Kevin de Leon, one of a host of candidates eying Feinstein’s seat, reacted immediately. In a state Hillary Clinton won by 61.6 percent to 32.8 percent, de Leon said Democrats should “not be complicit” in the “reckless behavior” of President Trump.

The backlash added to the “out of touch” murmurs that began during the 2016 fight over Proposition 64, which Feinstein opposed like a 1980s drug warrior.

“It is one more thing that suggests a notion that she is out of touch,” said Sacramento political consultant Steve Maviglio. “And that’s the last thing she needs right now. If someone brings that up as a campaign issue, it might have some legs. She is seen as being old school and this is one of those issues that could be worrisome.”

A Break With Her Protégé

Her hard stance against Prop. 64 illustrated the depth of Feinstein’s commitment to prohibition. The face of the Proposition 64 campaign was Gavin Newsom, California’s lieutenant governor and Feinstein’s political protégé. “She was his mentor,” said political consultant Jason Kinney, who worked on the Yes on 64 campaign.

Gavin Newsom, Feinstein's fast-rising political protégé, was the face of California's legalization campaign.

If anyone could sway Feinstein’s mind on legalization, it seemingly would be Newsom, her own brilliant apprentice. But there was no such transformation. “This,” the Senator told the Sacramento Bee, “may be one of the few issues I disagree with Gavin on.”

Newsom said he understood Feinstein was unlikely to come around. “She has a grandchild and she probably thinks this will normalize it,” he told the Bee last year. “I don’t know that it’s not already normalized.” He started to suggest he represented a different era than his political idol but stopped himself.

“I don’t want to say ‘generational’ because I don’t want to say that,” he said. “So I’m not going to say that.”

To call the 84-year-old Feinstein’s position ‘generational’ might be too easy a pass. Plenty of her generational peers have evolved their thoughts on cannabis, starting with her closest political contemporary in California: Gov. Jerry Brown.

The 79-year-old Brown worried about adult-use legalization on Meet the Press in 2014:

“The problem with anything, a certain amount is OK. But there is a tendency to go to extremes. And all of a sudden, if there’s advertising and legitimacy, how many people can get stoned and still have a great state or a great nation? The world’s pretty dangerous, very competitive. I think we need to stay alert, if not 24 hours a day, more than some of the potheads might be able to put together.

Despite those reservations, Brown has moved medical marijuana forward over the past decade. As attorney general in 2009, he drafted guidelines that offered a legal argument for dispensaries to distribute marijuana as medical collectives under Proposition 215 and 2003 state legislation, Senate Bill 420. As governor in 2015, Brown signed sweeping regulations to govern – and legitimize – the medical marijuana industry. And when voters passed Prop. 64, Brown moved quickly to implement the law.

Voting Her Fears, Even Against MMJ

Feinstein, by contrast, cast votes in the Senate in 2015 and 2016 against the Rohrabacher-Farr budget amendment, which prevents federal authorities from prosecuting medical marijuana patients who follow state law.

During the Proposition 64 campaign, Feinstein signed an opposition statement that warned of Big Marijuana luring children with television ads for legal weed. Kinney, the Prop 64 campaign spokesman, erupted over the opposing argument that “Proposition 64 will allow marijuana smoking ads in prime time, and on (television) programs with millions of children and teenage viewers.”

“These aren’t evidence-based arguments – they are scare tactics,” Kinney said, arguing that such ads were federally prohibited.

Nearly a year after voters approved Proposition 64, Kinney had no cross words for Feinstein. He was onto trying to elect her apprentice, Newsom, governor in 2018.

“The (Prop 64) campaign is over,” Kinney said. “The question was asked and answered by one of the largest margins in the country. I don’t think I am interested in throwing another log on that fire.”

Unchanged, Undeterred, and Still Formidable

Rusty Areias, the political strategist and former lawmaker who hosted the senator at his estate in 2012, says Feinstein remains a formidable and respected leader in California. He said she is unlikely to be toppled over cannabis or any single issue.

“Dianne is a force whether you agree with her or don’t agree with her,” Areias said. “She starts her position emphatically and she has also been a powerful force for moderation over the years. And once she makes up her mind, it is tough to change her.”

'I would campaign against Dianne Feinstein.' Steve DeAngelo, Co-founder, Harborside Health Centers

Areias suggested that Feinstein’s cannabis critics take note of her pro-death penalty speech she made before a chorus of jeers at the state Democratic convention in 1990 and then used the footage in a campaign commercial.

“Dianne is one of a kind, a very good politician,” Areias said. “If you’re a single-issue person, maybe you ought to find someone else. But you can’t judge a politician on one issue.”

Yet political pundits are already speculating on potential challengers from the left, including Senate leader de Leon, Los Angeles Mayor Eric Garcetti, state secretary Alex Padilla, Democratric House members Adam Schiff and Eric Stalwell and entrepreneur Joseph Sanberg, co-founder of the socially-conscious investment firm, Aspiration.com. “It could be a feeding frenzy,” said Maviglio, the Sacramento political consultant.

Fifty percent of voters view Feinstein favorably vs. 36 percent who disapprove, according to a poll released by Sept. 14 by the Institute of Governmental Studies at the University of California. That margin tightens 45 to 41 percent on the question of her re-election.

And Steve DeAngelo of Oakland’s Harborside dispensary is itching for a fight.

“I would campaign against Dianne Feinstein,” he said. “I don’t know how anyone in favor of cannabis reform would consider voting for her…The critical issue for democratically elected office holders in California is whether they are going to have respect for the voters who elected them or for a Justice Department headed by Jefferson Beauregard Sessions.”

Yet Lynette Shaw, an historic figure in the California medical marijuana movement who started working at Dennis Peron’s San Francisco Cannabis Buyers Club amid the AIDS crisis, isn’t sure she won’t end up marking her ballot for Feinstein.

Feinstein's long track record on other issues still gives many pro-cannabis voters pause. Some just can't vote against her.

Shaw founded one of California’s pioneering marijuana dispensary, the Marin Alliance for Medical Marijuana, months before California voters passed Proposition 215.

Five years later, in 2001, Shaw led a recall campaign against the Marin County district attorney, Feinstein ally Paula Kamena, alleging the D.A. still unfairly prosecuted medical marijuana cases. Feinstein ripped cannabis advocates as making exaggerated attacks. “She was furious we would recall Paula,” Shaw said. The recall was crushed by a 6-to-1 margin.

In 2011, the Marin Alliance was shuttered by a Justice Department property seizure order. But in October 2015, Shaw won a court battle restoring her right to distribute cannabis. U.S. District Judge Charles R. Breyer in San Francisco ruled that an injunction that kept the dispensary from reopening was rendered moot by the Farr-Rohrabacher Amendment against federal interference, which Feinstein opposed.

“Despite her closed-mindedness, people in California still voted to legalize marijuana” with Propositions 215 and 64, said Shaw, a long time Democrat who ran as a Libertarian for lieutenant governor in 2006 on a platform of “marijuana peace, not war.”

But Shaw is skeptical a pro-cannabis Democrat can sneak past the leading Republican candidate in California’s open primary to face Feinstein in the 2018 November runoff.

“She has been good on other issues, particularly with AIDS, and I have to applaud her for that,” Shaw said. “Dianne Feinstein has done a good job on everything but marijuana. I would rather have her than a Trump Republican.” So, after everything, she expects to vote for the senator.

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Peter Hecht Peter Hecht, former political writer and Los Angeles bureau chief for the Sacramento Bee, has been reporting on cannabis since 2009. His coverage has been honored for explanatory reporting in the "Best of the West" journalism awards and earned an Excellence in Journalism prize from the Northern California Chapter of the Society of Professional Journalists. Hecht is the author of the book “Weed Land: Inside America’s Marijuana Epicenter and How Pot Went Legit.” View Peter Hecht's articles