Book Commentary: “The Mayor of Castro Street” by Randy Shilts

Randy Shilts’ 1982 biography of Harvey Milk, The Mayor of Castro Street, provided much of the source material for the Oscar-winning films The Times of Harvey Milk (the documentary) and Milk (the dramatization). Anyone who has seen either of those films is familiar with the inspiring but tragic story of the first openly gay candidate elected to office in California, and there is even more context, nuance, and life to be found in the richer story the book offers. It really struck a chord with me and I highly recommend it to anyone who found either film inspiring. Below are some of the notes that stuck out to me as I read.

mayor of castro street cover

Note 1: The scale of thirty years, in political memory

The film Milk premiered just before the 2008 election, at the same Castro Theater that the film production had partnered with the owners and local businesses to restore. It was all coming full circle; the events of the film had taken place on that same block in San Francisco, thirty years earlier.

Milk premiere

The “Milk” premiere at the Castro Theater in 2008. You can see a “Vote NO on Prop 8” sign in the crowd.

However, that circle had already continued into its backside swing by the time the film spread to theaters in the rest of the country after the November 2008 election. True, the U.S., with the help of 55 Democratic electoral votes from California, had just elected a hopeful young Barack Obama who gave an election-night victory speech in Chicago’s Grant Park that mentioned gay Americans’ contribution to the country’s democracy. But the same day, California also passed Proposition 8, taking away the state’s existing legality for same-sex marriage in a regression of rights.

Thirty years spanned between Harvey Milk’s death and the passing of Prop 8– a period of time that, politically and culturally, was at once both an eternity and a flicker. So much had obviously changed in the world from 1978 to 2008. But for some social movements, little had really changed; as always, civil rights were teased by unreliable allies in need of a vote, then finally given ostensibly in the form of tenuous court decisions or provisions, only to be reduced or taken away by surges of reactionary populism.

The symmetry of thirty years also extends backwards in time, in a moment the book covers but the film doesn’t. During his speech to the Gay Freedom Day Parade in San Francisco in 1978, Harvey made a reference to the gay victims of the Holocaust, only a little more than thirty years earlier. The book describes how, while Harvey was a Jewish child growing up in New York, Germany’s active gay liberation movement was brutally cut short by fascism just as it was starting to gain momentum. This was not at all a flippant reference for Milk to make in his speech, as thirty years seemed like no time at all for a group who could envision the bottom falling out on their rights at any moment.

Harvey Milk at parade

Harvey Milk speaking at the 1978 SF Gay Freedom Parade

Note 2: Dianne Feinstein’s tenuous relationship with San Francisco liberals

Dianne Feinstein has been making a singular impact in California politics since 1969, and she plays a dramatic part of the story in the book. She saw Dan White in City Hall between when he killed Mayor Moscone and then Harvey Milk, heard the gunshots that killed Harvey, found Milk’s body, and had to announce the killings to the press minutes later. As President of the Board of Supervisors at the time, she became the new Mayor and started her term during the mourning, court drama, and riots of the murders’ aftermath.

Dianne Feinstein

Announcing the murder of Mayor Moscone and Supervisor Milk

She is well-respected for having led the city during the turbulent times well, but the book also describes the tension between her more moderate views and Harvey’s liberal populism. That tension still continues today while she is in the U.S. Senate representing California; her “Trump plus-minus” according to FiveThirtyEight was the highest among all Democratic U.S. Senators in the country after Trump’s first 100 days. In other words, more than any other Democrat in the Senate, she voted along with Trump far more often than her constituency wanted her to during Trump’s first 100 days. She approved many of Trump’s Cabinet nominees, like Mike Pompeo for Director of the CIA (this is a man who once criticized President Obama for closing CIA “black site” secret prisons and requiring interrogators to not torture).

Sen. Feinstein on FiveThirtyEight

Sen. Feinstein’s “Trump Plus-Minus” on FiveThirtyEight

Throughout the narrative in the book, we see several examples of political tension between Sup. Feinstein and the gay community. She clearly had no personal problems with homosexuality, even hosting a lesbian friend’s wedding in her backyard. But she also blamed gays for the homophobic backlash they faced when she publicly said, “The right of an individual to live as he or she chooses can become offensive. The gay community is going to have to face this. It’s fine for us to live here respecting each other’s lifestyles, but it doesn’t mean imposing them on others.” As the new mayor, she respected Harvey Milk’s wish to appoint a fellow gay activist, Harry Britt, to Milk’s spot in the event of his assassination, but she also abandoned Moscone’s promise to appoint a gay police commissioner.

Dianne Feinstein is only one personification of the political establishment who happens to be pretty easy to identify because of her singularly long, successful tenure in California politics. But reflecting on her presence in this book brings to mind an idea taking hold in me after the 2016 election, when many millennials like me preferred Bernie Sanders and had an “enthusiasm gap” upon Hillary Clinton’s nomination, only to have the unthinkable happen with Trump’s victory. Perhaps the majority of politicians were, are, and will likely to continue to be, either mostly in agreement with us but in need of constant reassurance that voters really have their back, or mostly against our views but willing to tone it down if heavily pressured to do so.

I used to think that calls to elected officials or attendance at rallies is only what you do in extreme cases; ideally, I thought, we’d just elect people who don’t need to be called and they will just do the right thing on their own. But I’m beginning to see that’s just not how it works. Barack Obama followed the lead of public opinion on same-sex marriage while using the “views are evolving” line. Even if Barbara Lee becomes the next U.S. Senator for California, or Elizabeth Warren becomes the next President, calls and rallies would still be needed to fuel their energy and strengthen backbones to take risks, “evolve” their positions faster, and do the right thing.

obama evolution on gay marriage

Note 3: Steps forward and steps back

In his final speech as President, Barack Obama consoled us after the election of his authoritarian nationalist successor, “Yes, our progress has been uneven. The work of democracy has always been hard, contentious and sometimes bloody. For every two steps forward, it often feels we take one step back. But the long sweep of America has been defined by forward motion, a constant widening of our founding creed to embrace all, and not just some.”

MLK Memorial

Obama’s words echoed those of Martin Luther King Jr.

Keeping that in mind, one of the ways I’ve been coping with the recent Trump victory is to seek out parallel stories from U.S. history and try to learn from how social progress eventually persisted. The Ken Burns Civil War documentary detailed an extremely violent step back in our country’s history out of which came the end of (most) slavery in the U.S. All the President’s Men features a step back for the office of President out of which came a victory for investigative journalism and Nixon’s resignation. Neither of these chapters ended without unfinished business still lingering ominously like a fault line, but I get a feeling of perspective from watching them.

Reading The Mayor of Castro Street fits into that category too. The book lends proof to Obama’s assessment, telling of many intricate steps forward and backward but leaving with you with a general sense of messy, slow, imperfect progress.

Step forward: In 1977, forty cities like Miami, Detroit, St.Paul-Minneapolis, and Seattle had passed gay rights ordinances protecting against discrimination in employment, housing, and public accommodations. Step back: as a response, conservative groups led by people like Anita Bryant, a media figure with no prior political accomplishments, began using fear tactics to push the “homosexual recruitment” narrative and get many protections rolled back. There was even a viable campaign in California called the Briggs Initiative to mandate the firing of all homosexual employees of public schools. (Slow) step forward: Eventually, the gay rights movement bounced back and defeated the Briggs Initiative, but it took years for other protections to return (a Florida gay adoption ban pushed by Anita Bryant took a full 30 years to be struck down by the court).

Anita Bryant

Anita Bryant campaigning against gay rights

Of course, the book’s most dramatic examples of a step forward followed by a step back are Harvey’s election then murder. While campaigning and in office, Harvey consistently spoke about the hope he wanted his election to give to gay people everywhere. He often mentioned a specific case about a boy from Altoona, Pennsylvania, who had called him twice: once when the boy was on the verge of suicide, and again after he had chosen not to commit suicide but rather to leave his abusive parents and seek out an accepting gay community. That story makes for one of the most emotional parts of the film and it had a huge effect on me when I saw it; reading it in more detail brought those feelings back.

In the firm “step back” category came the murder and its aftermath. Partially due to preventable mistakes by the prosecution described in the book, Dan White was only in prison for five years for planning and carrying out the killing of Harvey Milk and Mayor Moscone. One activist lamented that their deaths might set the liberal movement of the city back “ten, maybe twenty years.” When the verdict came in the less severe form of voluntary manslaughter instead of murder, the police reacted more violently than they had in years to the subsequent gay unrest. It must have certainly felt like a painful step back, and maybe even like a permanent one.

Note 4: What we are still dealing with

Unsurprisingly, the book brings up several key social issues we still are dealing with, forty years later now: real estate speculation, polyamory and open relationships, and destructive or violent demonstrations. For one reason or another, the film doesn’t really address any of them like the book does.

Real estate in San Francisco

The tension in San Francisco over housing affordability, tenants’ rights, gentrification, Airbnb violations, and real estate lobbying is such a long story that it needs another post to cover. Shilts’ book describes the real estate power in the city in the 1970’s and Harvey’s fight against it, and that power still clearly continues to cause problems today. In November 2016, the Board of Supervisors race in my District 1 of San Francisco (population 44,000) featured a real estate-friendly candidate who had over $650,000 of tech and real estate money on her side, giving her a 4-1 money advantage over the progressive, union-backed candidate. The progressive candidate just barely managed to win despite the money gap, but everyone knows the threat will return in the next election.

2016 SF supervisor campaign money

Much of the funds for moderate candidates like Ahsha Safai or Marjan Philhour (in my district) came from real estate interests and tech companies, while unions and local community groups backed progressives like Sandra Lee Fewer (who ended up defeating Philhour by only 1,000 votes).

Polyamory and open relationships

When the film came out in 2008, the big LGBT rights issue was same-sex marriage. But marriage, itself, is of course an institution with a ton of historical baggage that’s been used to control people (particularly women) and their sexual behavior. So while the legalization of same-sex marriage is surely a victory for civil rights, there is plenty of social soul-searching to do to normalize all kinds of healthy, consensual relationships inside and outside of marriage.

Whether it was respectability politics or just cut for time, the film didn’t really cover the fact that Harvey was open about having multiple lovers at the same time, saying, “We grow up with the heterosexual model, but we don’t have to follow it. We should be developing our own life-style. There’s no reason why you can’t love more than one person at a time. You don’t have to love them all the same. You love some less, love some more– and always be honest with everybody about where you’re at.”

NPR recently declared a “cultural moment for polyamory”, and it’s entirely possible that by 2038, the future side of the thirty-year symmetry after the film’s release, polyamorous and open relationships may be as recognized and celebrated in our society as same-sex marriages are now. But only if the necessary soul-searching really takes place.

Destructive or violent demonstrations

Finally, the White Night riots occurred when Dan White was only convicted of voluntary manslaughter, not murder (he only served 5 years in prison). Protestors took to the streets, eventually getting violent at City Hall and causing hundreds of thousands of dollars of damage. Shilts details the whole story of the unrest, and captures the anger and fear perfectly. It was really affecting for me to visualize the scene: the police cars on fire, the windows of City Hall broken, the police rushing without orders into a gay bar in the Castro and indiscriminately beating patrons in blind retaliation. The gay leaders, while initially trying to keep the protest from getting out of hand, defiantly proclaimed that gays had nothing to apologize for.

Of course, protests causing damage still happen today in San Francisco and the area (33 were arrested after doing thousands of dollars of damage to City Hall while protesting police violence in 2016), and we seem to be always struggling with the role of destructive or violent unrest in this country. It’s one of the most important conversations we should be having. Unfortunately, the film doesn’t show the riots, much less wrestle with the implications; it simply mentions them in a postscript. The documentary version’s coverage is here:

Frisco 500 protest

Frisco 500 protest at SF City Hall, 2016

Frisco 500 protest

Frisco 500 protest at SF City Hall, 2016

Note 5: Meeting our heroes

Shilt’s book is excellent in showing the full picture of Harvey Milk’s life, even those aspects that may not fit well into a 2008 Hollywood film. I’ll mention three:

The film does contain a line early on when Harvey reflects on his fortieth birthday in New York, and feeling like he was still figuring out what to do with his life. What it doesn’t explore, is that he actually was quite a conservative for the majority of his life. He volunteered for the Navy to fight Communism in Korea, worked on Wall Street, and even volunteered for the Barry Goldwater campaign. Only around turning forty did he become a liberal Democrat. This, ironically, put him even more at odds with the moderate Democratic establishment since he hadn’t “paid his dues.” Perhaps even more ironically, his empathy with the conservative way of thinking helped him build surprising political coalitions. Integrating together the seemingly-inconsistent intricacies of a person’s complete history takes some time and investment, one that the book thankfully made.

A second aspect was also related to Harvey’s service in the Navy. He often claimed publicly that the Navy had dishonorably discharged him when it learned he was gay. In fact, he was honorably discharged and it had nothing to do with his sexual orientation; he admitted to his campaign manager that he made up the story to get votes.

Harvey Milk in the Navy

The third moment happened when Oliver Sipple, a former Marine, stopped an assassination attempt against President Ford and became a media hero. Harvey Milk, by then in effect the voice of the gay community in San Francisco and well-connected with reporters, outed Sipple without his consent to the media so the spotlight would be on a gay hero figure. Sipple wasn’t out to his own family, and he angrily but unsuccessfully sued the newspapers for an invasion of his privacy.

Oliver Sipple

Oliver Sipple (left) stopping would-be assassin Sara Jane Moore (just to the right of the pole).

Note 6: Harvey’s love of the theater.

Those last two moments also are perfect examples of a central theme to Harvey’s story: the very fact that it is a near-perfect story with central themes in the first place. Throughout the changes in lovers, cities, and political views, Harvey always loved the opera and the theater. The book mentions how Harvey referred to City Hall as his “new stage” when his term began, and both book and film capture a great moment when Harvey tells one his friends that he always takes the City Hall stairs and not the elevator– so he can always “make such an entrance.”

Close friends recalled occasional moments where Harvey would divulge that he suspected that he would be killed for his outspokenness, even before the death threats started regularly arriving. But he kept his activism going, because he knew his story could one day provide hope to others. He even recorded a “political will” and sent copies to three close friends, in which he spoke the immortal line, “If a bullet should enter my brain, let that bullet destroy every closet door.”

In his way, Harvey was performing for all of us, and in a sense he is still performing through the films and tributes.

Shilts ends his book with a beautiful parallel between Harvey’s life and the larger gay experience, an assessment that Harvey may have agreed with: “The entire story of the life and death of Harvey Milk rang so true to the experiences of gays throughout the country because it already seemed a part of the homosexual collective unconscious, even before it happened; that it happened to one man in San Francisco was a mere formality. It had been happening for a long time.”


Honestly, the movie Milk is part of why I wanted to move to San Francisco, which I eventually did in 2013. I loved the romance of an inclusive community built by and for people who had been told they did not belong in the places they came from. Just a couple years later, I worked at an office just down the block from where Harvey’s camera shop once stood (it’s now a gift shop for the Human Rights Campaign, with a plaque commemorating Harvey), and crossed the rainbow crosswalk at 18th Street and Castro nearly every day.

rainbow crosswalk

The crosswalk at 18th St. and Castro, with the bar Harvey’s across.

I’ve been wildly fortunate in a lot of ways in my life, among them being able-bodied and with racial and gender privilege, but bridging across the differences in social identity is a beautiful, universally human element to the story of Harvey Milk that I identified with so deeply in 2008 and still is a core part of me now. Reading The Mayor of Castro Street uncovered all those emotions and made them fresh to me again, reminding me why I love my adopted city, why it’s always worth fighting for, and how hope lives on.

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