Dianne Feinstein, like some more famous denizens of San Francisco, must occasionally reflect on what a long, strange trip it’s been.

The near derailment of Brett Kavanaugh’s nomination to the U.S. Supreme Court once again made Feinstein the archvillain for conservatives, a role she played in the 1990s when spearheading a federal assault weapons ban. The Left briefly saw California’s senior senator in a positive light, a hero who fought the good fight by any means necessary. But that moment quickly faded. Now Feinstein finds herself in a more familiar spot: in the spitball crosshairs of her fellow progressives.

As Californians prepare to vote for the office she has held since 1992, the latest poll shows Feinstein at just 45 percent (a point below her high-water mark for the general election) and just nine points ahead (her narrowest lead) of Kevin De Leon, a Democrat, who, as a result of California’s unique electoral laws, will run against Feinstein in the vote on Tuesday. She appears a near lock to win reelection for the fifth time, but a senator of her stature fighting off a serious internecine challenge and losing the endorsement of her own party is unusual. 

This is par for the course for Feinstein. The race appears as her half-century in electoral politics in microcosm. However swiftly Feinstein rushes Left, she never quite catches up to Golden State progressives.

Elected to the San Francisco Board of Supervisors 50 years ago as a good government liberal championing gay rights and other progressive causes, Feinstein soon realized that satisfying her city’s Left came as a fool’s errand. In December 1976, after her third-place finishes for mayor the previous year and in 1971, Feinstein’s maid noticed an explosive device in a flower pot outside a window in her home. That same year, someone shot up the windows of her beachfront getaway.

The perpetrators? The New World Liberation Front, a left-wing terrorist organization so incapable of differentiating friends from enemies that in 1979, leader Ronald Huffman plunged an ax into the skull of the group’s only other member, Maureen Minton, before beating her lifeless body with a two-by-four to knock out the demonic spirits that resided therein. 

Though targeted by the city’s lunatic fringe, Feinstein occasionally joined them. Not a cheerleader for Peoples Temple, she nevertheless joined a unanimous board of supervisors in presenting Jim Jones with a “certificate of honor” in 1976 “in recognition of his guidance and inspiration,” his “humanitarian programs,” and his “tireless and invaluable contributions to all the people of the Bay Area.” As documented in Cult City: Harvey Milk, Jim Jones, and 10 Days That Shook San Francisco, Assemblyman Willie Brown, Mayor George Moscone, District Attorney Joe Freitas, and other power players enthusiastically drank Jim Jones’ Kool-Aid in San Francisco—before less powerful people did so, with more disastrous consequences, in South America. Feinstein, though operating at greater distance from the Temple, got caught up in Jones’ seduction of the city.

More mainstream elements within San Francisco’s Left expressed displeasure with Feinstein in more conventional ways than the New World Liberation Front. Gay rights icon Harvey Milk despised Feinstein perhaps more than anyone he encountered during his brief sojourn in politics. The fast-talking Easterner, whose camera store attracted more street people than customers, viewed Feinstein as a patrician schoolmarm disconnected from the times and the town. When Feinstein encouraged homosexuals to tone down their antics at parades and sought to corral sex shops away from neighborhoods and into more industrial parts of the city, Milk attacked. He denounced Feinstein as playing to “Bible-thumping, flag-waving, law-and-order voters” (fighting words in San Francisco) and alternatively declared her ideas “out of the ’50s” and resembling “19th-century moralistic legislation.”

Upon assuming his seat on the board of supervisors, Milk refused to vote for Feinstein as president of the body despite her main opponent embracing positions on the extreme right edge of the Democratic Party spectrum. When Feinstein won the presidency, the board agreed to take a presumably perfunctory vote to make the winner a unanimous choice. Milk recalcitrantly, and tellingly, again voted against the daughter of San Francisco. 

“Harvey saw her as everything he really detested,” Ray Sloan, Supervisor Dan White’s chief of staff, told me in an interview for Cult City. “A rich woman with a good education and everything going her way. She was clueless on what culturally was changing in the city. He made fun of her on all that—Queen Dianne, and a queen in the old sense!”

The gunman who killed Harvey Milk did not kill the Left’s disdain for Feinstein. He inflated it. Assassin Dan White entered the board of supervisors as a protégé to Feinstein. On his first day in office, he engineered her ascension to the board presidency in an uncharacteristic example of deft political gamesmanship. On his last day in city hall, he elevated the board president—someone likely to soon exit politics after illness, the death of her second husband, multiple defeats, and the threats that caused her to carry a handgun (a fact raised at White’s trial to the defendant’s benefit)—to the mayor’s office.

When San Francisco leftists sought to establish a political narrative portraying the assassinated Milk as a martyr for gay rights, Feinstein, who retains possession of White’s diaries, refused to go along. “This had nothing to do with anybody’s sexual orientation,” she later reflected in an interview. “It had to do with getting back his position. Dan White was a troubled man under a lot of pressure, not the least of which was an inability to earn a sufficient living for his wife, who was a teacher, and child. And I believe they were expecting a second child.”

As mayor, Feinstein stewarded San Francisco out of the 1970s, a chaotic decade featuring a police strike, Zodiac and Zebra Killers, the Symbionese Liberation Army and New World Liberation Front terrorizing the Bay Area, Peoples Temple wielding a powerful influence on city politics, the Milk-Moscone assassinations, unflattering popular culture portrayals in Dirty Harry and The Streets of San Francisco, and much else depressing besides, and into the 1980s that reasserted the City by the Bay as that mecca for money and culture that visitors recognize today. Still, the decade posed challenges, the AIDS epidemic chief among them.

Again, Feinstein alienated her party’s left flank. As gay men wasted away, her administration moved, slowly, to close the city’s bathhouses. “I believe it will save lives by preventing the spread of this lethal and tragic disease,” Feinstein explained. “Investigators have documented that activities medical science tells us spreads AIDS are occurring in these facilities.”

Critics labeled the Feinstein administration’s aims the work of “uncaring and unscrupulous theocrats.” Even as gentle a suggestion as safe sex was met with derision. “I didn’t become a homosexual so I could use condoms,” Konstantin Berlandt, a co-chair of the city’s gay pride parade and subsequent victim of the deadly disease, quipped. Protestors favored the mantra “Out of the Baths, Into the Ovens” to decry the mayor’s policies.

Ultimately, Feinstein, who boldly supported gay rights during her first run for office in 1969, found herself at odds with all but one of her city’s major gay rights organizations in successfully closing the bathhouses most egregiously threatening public health. Again, she collected enemies.   

Her subsequent career featured flip-flops on capital punishment, a vote for the Iraq war, and support for the Patriot Act. So, while Republicans may view Feinstein through the lens of the assault weapons ban or her over-the-top effort to derail the Kavanaugh nomination, many Democrats have also had trouble getting past her deviations from party orthodoxy.

Though no Scoop Jackson or even Daniel Patrick Moynihan, Feinstein still strikes as an atavism. In an age of polarized politics, she, here and there, said “no” to powerful forces within her party. While this may gain a politician respect outside of the party, the party faithful prefer those in their party to remain, well, faithful.

Conservatives, who view liberals with as much nuance as liberals do them, look on perplexed. How could the woman who tried to take away their guns and spike Brett Kavanaugh’s Supreme Court nomination face hostility from her Left? The Democratic Party’s current shift Left, as Ed Rendell and other party elder statesmen worry about, plays a role in Feinstein’s present troubles. But events more deeply rooted in the past do a better job explaining why, instead of enjoying a victory lap, the 85-year-old senator is enduring a bumpy road to reelection.

Daniel J. Flynn, a senior editor at The American Spectator, is the author of Cult City: Jim Jones, Harvey Milk, and 10 Days That Shook San Francisco (ISI Books, 2018).