Michael Kruse is a senior staff writer for Politico.

Jackie Richter is the foul-mouthed, frank-talking owner of Heels and Hardhats, a small construction company near Rockford, Illinois. For almost half a century, she lived as a man—an existence the 58-year-old transgender woman told me felt fundamentally wrong, like always having to wear her right shoe on her left foot. But in the summer of 2010, a few years after she finished transitioning, she applied for a United States passport saying she was female. That September, she got it. This, she said recently, was the first time she felt the full support of the federal government. The document saved her business, saved her family, and—she believes—saved her life.

And for this, she credits Hillary Clinton.


“None of it would have been possible without what she did,” Richter said. “She was a forerunner on this.”

It’s not a label typically associated with the presumptive Democratic presidential nominee. Over her quarter-century of national public life, Clinton mostly has enjoyed broad support from LGBT voters, donors and activists, but many of them considered her a laggard on the litmus-test issue of marriage equality, which she didn’t endorse until 2013. And during her surprisingly drawn-out primary fight with Senator Bernie Sanders, Clinton consistently was cast as the more centrist candidate. Sanders, not Clinton, was the full-throated social revolutionary.

But five years before the Supreme Court ruled in favor of same-sex marriage and President Obama lit up the White House in the colors of the rainbow, Hillary Clinton and her staff at the State Department made a change that for thousands of people was exactly that—revolutionary. Clinton enacted a new rule making it easier for transgender people to register their identities on their passports. Sexual reassignment surgery was no longer necessary; all that was required was a doctor’s note. At the time, this was the most pro-transgender action by the federal government ever, and—coming a full six years before the Pentagon announced transgender troops could serve openly—it stands as one of the most progressive things Clinton has ever done. In a single stroke, she made the passport the best way—for some, the only way—for American citizens to prove they were who they were. For transgender people, it was—according to recent conversations I have had with gay, lesbian, bisexual and transgender experts and advocates—“huge,” “enormous,” “monumental.”

The crowd celebrates outside of the Supreme Court in Washington on Friday, June 26, 2015, after the court declared that same-sex couples have a right to marry anywhere in the United States. | AP Photo

If all this is news to you, though, there’s a reason: It was implemented with deliberately little fanfare, according to people I talked to who were involved in the process. The State Department issued a brief “media note.” Clinton was not quoted in the relatively scant coverage in the mainstream press. The Associated Press wrote seven paragraphs, CNN.com five. Nothing ran in the New York Times, the Washington Post or POLITICO.

After being disqualified from Miss Universe Canada because she was born male, Jenna Talackova, shows her Canadian passport as proof that she is female. The Miss Universe Organization reversed their decision in April 2012.

Until now, nobody has looked this closely at this episode of Clinton’s career—how it happened, and why—but in many ways it is a quintessential Clintonian collision of progressive policy and cautious politics. It reads less like a tale of a trailblazer and more like a case study of constitutional circumspection.

“I think they were squeamish,” Mara Keisling told me, talking about the lack of publicity. She’s the executive director of the National Center for Transgender Equality, one of the handful of advocacy organizations that met with State Department officials about LGBT initiatives at the outset of Clinton’s four-year tenure as Secretary of State. “I think we were squeamish.”

“They wanted to do good work for trans people,” Keisling explained, “but wanted to do it in a way that didn’t cause a big uproar.”

Clinton, thought Julie Dorf, a senior adviser for the Council for Global Equality, was “quite comfortable” with the policy “personally.” But “politically,” Dorf told me, “she’s so much more calculating and cautious.”

In the current presidential campaign, with polling showing that a majority of Americans think gay people should be allowed to get married but not that transgender people should be able to use the bathrooms they want, Clinton has talked plenty about her LGBT record, and about her intention to do even more if she’s elected president. Rarely, however, has she mentioned the transgender passport policy, even when it might have come in handy politically.

They wanted to do good work for trans people, but wanted to do it in a way that didn’t cause a big uproar.”

Not in debates. Not in town halls. Not in speeches. Not when she’s been asked specifically about violence against transgender women. Even this past spring, when North Carolina’s Republican governor signed a law banning transgender people from using public bathrooms that correspond with their gender identities, Clinton responded with a tweet. “LGBT people should be protected from discrimination under the law—period,” she wrote.

And she definitely hasn’t called attention to the email she received in 2011—made public because of the investigation into her private email server—in which Richter wrote to her “in great gratitude.” Richter’s name was redacted prior to the State Department’s release of the emails, but I found her using public records of Illinois businesses. Her email to Clinton was a message to which Clinton responded—quickly, personally, privately.

At left, Jackie Richter talks with her wife Cyndi in the kitchen of their home in May in Byron, Illinois. On the right, Jackie poses for a portrait a construction site operated by her company, Heels and Hardhats Contracting, in DeKalb, Illinois. | Joshua Lott for Politico

It is impossible to measure how this public reticence might have affected Clinton’s standing with the diversity-minded, far-left wing of her party, whether it cost her votes in the primaries or support heading into the general election. But Richter, whose business was bolstered by state certification as a female-owned enterprise thanks to her new passport, got angry talking to me about LGBT people she knows who favor Sanders over Clinton. For them, she said, she had a message: “Look, motherfuckers, how could you do this to this woman when she’s done so much for this community?”

***

Clinton had come into her role at the State Department with an uneven record on LGBT issues. She marched in the gay pride parade in New York in 2000 as a candidate for U.S. Senate, becoming the first First Lady to do that, and she did it again in 2006—another election year—but she was resolutely against same-sex marriage when she was a candidate for the Senate, when she was in the Senate, and throughout her initial presidential campaign. “I think marriage is as marriage has always been—between a man and a woman,” she said in 2000. “I prefer to think of it as being very positive about civil unions,” she said in 2007.

Hillary Clinton has a varied record on LGBT rights, opposing marriage equality throughout her years in the Senate but establishing equal protections for the domestic partners of Foreign Service members during her time at the State Department. Above, Clinton waves to the crowd during the annual gay pride parade June 25, 2000, in New York City. | Chris Hondros/Newsmakers

Some LGBT people remained leery of her, too, because her husband as president in the 1990s had signed the Defense of Marriage Act, which defined marriage as between a man and a woman, and also the policy of “Don’t Ask, Don’t Tell,” which effectively closeted gay military members. Both laws were deeply disappointing to LGBT people, who had considered President Clinton an ally and felt betrayed. Even so, in 2008, according to polls at the time, LGBT voters in Democratic primaries preferred Hillary Clinton to Barack Obama, who at that juncture didn’t support marriage equality, either.

And in late 2008, when Clinton returned to the Senate after conceding the race to Obama, her staff urged her to voice full support for marriage equality. Polling was showing rapidly increasing acceptance, and they wanted her to get out in front of that movement. That didn’t happen, obviously—Obama asked Clinton to be Secretary of State, and she accepted.

When Clinton started as Secretary of State, in January of 2009, she inherited a department that LGBT staffers had seen as indifferent to their rights during the George W. Bush administration. They grumbled that the department would pay for their pets, but not their partners, to travel to posts around the world. Clinton, on the other hand, signaled immediately her commitment to LGBT issues, setting up meetings—personally or with top staff—with advocacy groups like the Council for Global Equality, the National Center for Transgender Equality and the Human Rights Campaign, as well as the in-house organization called Gays and Lesbians in Foreign Affairs Agencies. They had long lists of pent-up requests. The Clinton State Department addressed them.

“We were always getting a yes,” Jon Tollefson, a GLIFFA president during Clinton’s tenure, told me, “so we just kept going.”

To LGBT people and advocates, within the State Department and around the country, what Clinton was doing wasn’t a total surprise. The extent of her commitment, though, was a revelation.

To LGBT advocates, what Clinton was doing wasn’t a total surprise.



The extent of her commitment, though, was a revelation.

In May of 2009, four months after Clinton took over at the State Department, Kerry Eleveld, a reporter for The Advocate, the LGBT newspaper, got a copy of a draft of a letter Clinton had written that was to be sent to GLIFAA employees. “Historically, domestic partners of Foreign Service members have not been provided the same training, benefits, allowances, and protections that other family members receive,” the document said. “These inequities are unfair and must end. … [T]he Department will provide these benefits for both opposite-sex and same-sex domestic partners because it is the right thing to do.”

“She fixed that as soon as she could,” said Michael Guest, a gay career foreign service officer who in 2007 had quit to protest the situation at the State Department in the Bush administration. Obama then put him on the department’s transition team. “It was, like, the first thing she did, so I gained a lot of respect for her.”

Clinton also was the first Secretary of State to give a speech at the State Department’s annual event marking gay pride month. And in 2011, in Geneva, in remarks for International Human Rights Day, and to an audience that included diplomats from countries in Africa and the Middle East with retrograde LGBT rights records, she said, “Some have suggested that gay rights and human rights are separate and distinct; but, in fact, they are one and the same.”

Judging from back-and-forth in the released emails, Clinton kept up with news of gay rights abuses and violence against LGBT people around the world as well as states and nations moving forward on marriage equality. She even taped an “It Gets Better” video.

But nothing Clinton did on this front was more ahead of its time than the transgender passport policy.

“We had never, and I mean never, had the federal government do a pro-trans policy before,” said Keisling from the national transgender group.

We had never, and I mean never, had the federal government do a pro-trans policy before.”

Passports with appropriate gender markers allowed transgender people to travel more safely abroad. But they had a big impact domestically, too: Passports are a legal form of identification everywhere in the U.S., so a new passport rule would enable them to get their ID re-issued even if they lived in red states with conservative legislatures and restrictive driver’s license regulations. It also would have considerable symbolic value: “It says, ‘This proves who I am,’ and it has the seal of the United States on it,” said Rick Garcia, the founder of Equality Illinois and a longtime LGBT activist.

From their corner of the federal government, a quieter perch relative to the day-to-day partisan wrangling over on Capitol Hill, Clinton and her staff realized they had the power to make a significant advance in LGBT rights.

“She’s a policy wonk at heart,” said Richard Socarides, a Democratic political strategist and LGBT activist who has known Clinton for decades, “and this was a policy idea she could do something about herself—you know, she didn’t need to work with Congress.”

Harold Koh, a former legal adviser at the State Department who worked with Clinton, told me her thinking about the passport policy was simple: “If you live your life trapped in a gender identity that’s not you, that dramatically restricts your sense of self—and why should government be a party to enforcing this oppressive tradition?”

So in early June 2010, the State Department sent out a brief “media note.” “Beginning June 10,” it read, “when a passport applicant presents a certification from an attending medical physician that the applicant has undergone appropriate clinical treatment for gender transition, the passport will reflect the new gender.”

In spite of the limited mainstream press coverage, the LGBT media paid more attention—and news of the policy rocketed around the transgender community.

“When the ink was dry on the paper,” Richter said, “we all knew about it.”

***

For Richter, it had been a long, difficult decade. She started secretly wearing women’s underwear, she told me, around 2000. She had, in a closet in her home office, high heels and dresses and wigs and a mirror. During the day, she kept it locked. At night, she left lipstick stains—MAC Russian red—on the filters of her Marlboro Lights. Richter’s wife worried her construction-worker husband was having an affair. Richter cried and told her the truth. Over several years beginning in 2004, Richter transitioned using hormones and “a little bit of plastic surgery,” but not full reassignment surgery because it was too expensive—especially at a time when her transition was threatening her ability to make a living. She sent out hundreds of resumes, often hearing, she said, that she was free to dress up however she wanted—but not on the job. At home, at first, her wife and her daughters struggled to adjust. The personal and financial strain wore on her and her family. More than once, she swallowed too many pills, closed her eyes, and was disappointed when she woke up.

But in September 2010, four months after the State Department’s new policy had taken effect, Richter’s passport arrived. In practical terms, it helped her attain state certification as a female-owned business—something her Illinois driver’s license already identifying her as female hadn’t had the power to do, she said. The state certification eventually led to more work, she said—a federal stamp of approval. But there was much more to it than that, and this is what she contacted Clinton about.

“Dear Madam Secretary,” Richter wrote in October 2011. “I am writing you today in great gratitude for the impact you have made in our community and my family.”

My country accepts me as a woman and this state should … as well,” Richter wrote. “My passport reads ‘female.’ … I am who I am.”

She told Clinton Heels and Hardhats now was on the way to being a Female Business Enterprise—the first such recognition in Illinois for a company run by a transgender woman.

“When I went to my state, to begin … the process, I stated, ‘My country accepts me as a woman and this state should … as well,” Richter wrote. “My passport reads female. … I am who I am.

In October 2010, Jackie Richter wrote Clinton to thank her for the passport policy change. “I remain committed to doing everything I can as Secretary of State to ensure that all people are given the opportunity to fulfill their God-given potential,” Clinton wrote in response. “Please know you have my best best wishes for great success with your new contracting company.” | Joshua Lott for Politico

“Thank you for your acceptance and taking action where others before have turned their backs,” she concluded.

“Respectfully …”

Richter sent it to Rocco Claps, the director of the Illinois Department of Human Rights. Claps sent it to Betsy Ebeling, one of Clinton’s best friends from her suburban Chicago childhood. Ebeling sent it to Clinton. “I am very proud of you,” Ebeling wrote to Clinton.

“Thanks, my friend,” Clinton wrote back. “I will respond directly.”

And she did. Two weeks after Richter’s forwarded email showed up in her inbox, Clinton wrote a letter, on her Secretary of State stationery, addressed to Ms. Jackie L. Richter.

“Dear Ms. Richter,” Clinton wrote.

“Rocco Claps passed along your brave and thoughtful message; thank you for sharing your story with me and for your kind words of support. I am always inspired by the strength of my friends in the LGBT community, and am so heartened to hear that our policy change at the State Department has made a real impact in your life. While you have faced many challenges and hardships that no person should ever have to face, your leadership and determination is helping secure progress for the future.

“I remain committed to doing everything I can as Secretary of State to ensure that all people are given the opportunity to fulfill their God-given potential. Please know you have my very best wishes for great successes with your new contracting company.

“With warm regards to you and your family, I am

“Sincerely yours,

“Hillary Rodham Clinton.”

Richter put the letter in a frame and hung it on the wall of her office, not far from the closet where she used to wear dresses and lipstick and hide.

***

Clinton’s last day as Secretary of State was the first day of February 2013, and her departure freed her to be more vocal about where she now stood on marriage equality. After a conference call with aides, including a speechwriter, “to map out what she wanted to say,” according to Jonathan Allen and Arnie Parnes in their book, HRC: State Secrets and the Rebirth of Hillary Clinton, she came out in support of same-sex marriage—“personally and as a matter of policy and law”—in a six-minute video released by the Human Rights Campaign. The Economist sniffed that her shift was “farcically late.”

The following year, in Hard Choices, a second memoir generally seen as an opening salvo to her expected second presidential run, she wrote at length about her time as Secretary of State. She mentioned the transgender passport policy on page 578. “We also made it easier for Americans to change the sex listed on their passport …”

It caught the eye of Terry Gross.

“Did you have to sneak that in without a lot of attention?” Gross asked Clinton on her National Public Radio interview show that June. “I mean, I didn’t know you’d done that. But I have a feeling, if a lot of people had known you’d done that, you would’ve gotten a lot of pushback for that. I mean, ‘cause there’s still a lot of people in our country who oppose gay rights and would probably even more so oppose, like, any recognition of the transgender community.”

Gross, who had invited Clinton on the air because Clinton had a book to promote, went right to the crux: “So did you do that on”—here she laughed a little—“the quiet?”

“Well,” Clinton answered quickly, “I don’t know how quiet it was.” Then she made an immediate pivot to her overall LGBT record at the State Department and the related efforts in the Obama administration.

But Gross was right. Clinton and her staff at the State Department—and the advocacy groups they were working with—had made precisely this assessment. It was a time-tested piece of the activist playbook. “That’s the approach I always took at HRC,” said Elizabeth Birch, a longtime LGBT advocate who was the executive director of the Human Rights Campaign from 1995 to 2004. “I didn’t want them screaming it from the rooftop. Why rattle the cage? Let’s get it implemented and have it take hold.” Gross, though, sensed Clinton’s discomfort, or even an unwillingness to acknowledge this strategy.

After a break, she returned to the subject—Clinton “made it easier for Americans to change their gender on their passports,” Gross told listeners again—and then she got blunt.

“So what’s it like when you’re in office,” Gross asked Clinton, “and you have all these political calculations to not be able to support something like gay marriage that you actually believe in? … Correct me if I’m reading it wrong.”

Clinton cut in, her tone sharpening. “I think you’re reading it very wrong,” she said.

“I am just trying to clarify so I can understand,” Gross said during the testy exchange.

“No, I don’t think you are trying to clarify,” Clinton responded.

Wrote prominent gay blogger Andrew Sullivan at the time: “… she got pissed when merely asked how calculated her position on this was. … Was political calculation as big an influence as genuine personal wrestling? She’s a Clinton. They poll-tested where to go on vacation. Of course it was.”

***

Due credit, though: Two years removed from the eye-opening Gross interview, on account of her record and her platform—as well as the historic pace with which the LGBT movement has made gains—Clinton to this point has run the most LGBT-friendly presidential campaign in the history of this country.

Her campaign manager, Robby Mook, is openly gay—a first—and she has made clear that she not only intends to continue Obama’s progressive agenda on this front but wants to be essentially the LBJ of the LGBT movement. Her campaign website has its own LGBT issues page, where she promises she will work to “ensure full federal equality for all LGBT Americans”— a reference to the Equality Act, currently pending in Congress, which is sort of a 1964 Civil Rights Act for LGBT citizens, across-the-board protections against discrimination based on sexual orientation or gender identity. “I would be honored to sign it into law as President,” Clinton wrote in her Human Rights Campaign candidate questionnaire. “That will be my highest priority,” she said in a town hall in October. The same month, in New York, in a speech to the Human Rights Campaign, she told an audience that was chanting her name, “You helped change a lot of minds, including mine. I am personally very grateful for that.” In debates with Sanders, even when they weren’t asked any LGBT questions, she incorporated nods to LGBT people and rights in her opening and closing statements. She has been endorsed by LGBT publications, LGBT organizations, transgender-specific organizations and the political action committee formed by the leaders of the Congressional LGBT Equality Caucus.

“Senator Clinton, Secretary of State Clinton and candidate Clinton—she has a record that really is unmatched when it comes to LGBT rights,” said Winnie Stachelberg, an executive vice president at the Center for American Progress.

“America has moved a long way in the last seven or eight years in terms of gay and lesbian and transgender people,” Guest told me. “It’s a different conversation than we were having. And she was a leader.”

Jackie Richter and her wife Cyndi outside their home Byron, Illinois. | Joshua Lott for Politico

Said Michael Posner, a former Assistant Secretary of State who worked closely with Clinton on her LGBT efforts: “She’s the most forward-leaning Secretary of State we’ve ever had on these issues.”

And yet: Last fall, in a round of released emails, there was Clinton, worried about a State Department decision from 2011 to sub the words “mother and “father” with gender-neutral “Parent 1” and "Parent 2” after it had become public in the pages of the Washington Post. She couldn’t help but do the political math. “I’m not defending that decision, which I disagree w(ith) and knew nothing about, in front of this Congress,” she emailed to top aides Cheryl Mills and Jake Sullivan. “We need to address this today or we will be facing a huge Fox-generated media storm,” she added.

Earlier this year, after the funeral of Nancy Reagan, Clinton praised the Reagans on the issue of HIV and AIDS, saying in an interview on MSNBC that they “started a national conversation, when before nobody would talk about it”—when in fact they were conspicuously tardy in mere public acknowledgment of the health crisis that was a devastating, principal part of life as a gay person in the 1980s. Clinton quickly backtracked, saying she “misspoke.” “For that,” she said in a statement, “I’m sorry.” Was it mere forgetfulness? A sign she was paying only so much attention to gay issues at that time? An indication of her naturally centrist impulses? The mistake left ardent LGBT supporters of hers baffled. “So bizarre,” AMERICAblog editor John Aravosis said when we talked.

And while Clinton certainly has spoken over the last year about the importance of transgender-specific rights—“We need to say, with one voice, that transgender people are valued, they are loved, they are us,” she said in her October Human Rights Campaign speech—she has talked the least about the ‘T’ of LGBT and seldom has invoked the earliest, most pro-transgender piece of her record. In February, when she was asked about violence against transgender women by an audience member at a town hall in New Hampshire, she called it “a terrible problem” and highlighted her 2011 speech in Geneva. Since March, any reaction of hers to North Carolina’s anti-transgender House Bill 2 has not included any reference to the passport policy that was so important to people like Jackie Richter. The irony, of course, is that Richter’s story provides such a personal and profound justification for the policy.

I’m sure she can be a bitch, like the rest of us women,” Richter said in her no-BS smoker’s voice. “But for the most part, she does the right thing.”

Since she got her passport, Richter told me, Heels and Hardhats’ business has gone from $100,000 a year to more than $2.5 million. She said she’s hoping to hit $5 million this year—and “none of it would have been possible without Hillary,” she said. She doesn’t seem terribly troubled by Clinton’s reluctance to discuss it. What she actually did, as opposed to what she has said or not said, is what has made the biggest difference for her. “I’m sure she can be a bitch, like the rest of us women,” Richter said in her no-BS smoker’s voice. “But for the most part, she does the right thing.”

Maybe Clinton and others in her campaign will talk more about the passport policy in between now and November 8.

“It’s probably something she’ll do more of as we move into the summer and the fall,” said Stachelberg from the Center for American Progress.

“I hope going forward they will do that,” Barney Frank, the gay former Congressman from Massachusetts and a Clinton supporter, told me.

Or maybe they won’t. “You campaign for the votes you don’t have—not for the votes you do have,” Frank said.

Last week, I got on the phone with Dominic Lowell, the Clinton campaign’s director of LGBT outreach.

“I reference her tenure as Secretary of State,” he told me. “I think she did so many amazing things there.”

Including the transgender passport change? I asked Lowell if people he encounters on the trail even know about it.

“I have to say it varies,” he said.

“I guess I couldn’t say it’s universally known,” he added.

If I were to see Hillary in person,” Richter said, “I would give her a hug and thank her for her courage, doing what she did for our community.”

Lowell was familiar with the email Richter had sent to Clinton because I had sent it to Xochitl Hinojosa, a Clinton communications staffer who was on the call, too. I told Lowell more about Richter’s story, and I asked if it was the kind the campaign might like to feature at some point. Richter, on her end, had told me she would have no problem with that, and her wife told me the same. “If I were to see Hillary in person,” Richter said, “I would give her a hug and thank her for her courage, doing what she did for our community.”

Hinojosa stepped in.

“We’re always looking for ways to highlight Hillary Clinton’s record,” she said, “and those that have been impacted by it, and ways we can tell a story.”

Before we hung up, I told them I have Richter’s number, should they want it.