UP THE HILL: HOW CLINTON’S TOP ADVISOR IS MOVING ON FROM THE 2016 ELECTION

Photo courtesy of Barbara Kinney   Ron Klain, Hillary Clinton, Jake Sullivan, Ann O’Leary ’93 and Sara Solow meet after the primary democratic debate in Flint, MI on March 6, 2016.

Photo courtesy of Barbara Kinney 

Ron Klain, Hillary Clinton, Jake Sullivan, Ann O’Leary ’93 and Sara Solow meet after the primary democratic debate in Flint, MI on March 6, 2016.

BY  LINDSEY MCGINNIS ’18

Elle magazine described her as a key member of Hillary Clinton’s “Girl Squad.” To Fortune.com readers, she was “the wonk shaping Hillary Clinton’s plans for the country.” POLITICO named her one of the top 50 “thinkers, doers and visionaries” transforming American politics in 2016.

But at 11 a.m. on Nov. 9, Ann O’Leary ’93 didn’t know what to do. As Clinton delivered her concession speech, O’Leary was lying on the couch in a half-packed pool house outside of D.C., wondering what comes next. All she had was a car full of official documents — policy ideas, cabinet picks, transition schedules, etc., all the blueprints necessary to usher in a new presidency — and a 24-year-career defined as much by the Clintons as by her passion for family and education policy.

O’Leary was one of many staff members, advisors and volunteers blindsided by the 2016 election. As the former co-director of the Clinton-Kaine transition, and one of three senior policy advisors coordinating campaign staff, O’Leary knows this better than most. She hadn’t moved her kids, Violet and Emmett, from Oakland to D.C. yet, but that had been the plan. She hadn’t found an apartment near the White House, but it was in the works. If you caught her that morning after the election, it might have looked like O’Leary lost everything — her career, her marriage, her privacy, her president. Over a year later, the two-time White House veteran has managed to course-correct, but there are still hurdles O’Leary has yet to surpass. Clinton’s campaign memoir, “What Happened,” sits on her table, for instance, hardly half read, the memories still too raw to replay. So how did this scrappy policy nerd with a lopsided smile become a top advisor to one of the world’s most powerful women, and where did it all go wrong?

O’Leary’s Clintonland journey began in 1993. Immediately after graduating from Mount Holyoke, where she was an active member of the College Democrats, O’Leary moved to Washington. The Orono, ME native said that her family had to take out a second mortgage to put her through college, so she couldn’t afford to take unpaid internships like her friends. Volunteering, however, presented some interesting opportunities. 

For a year, O’Leary would wake up at 4 a.m., go to the White House and read through the day’s major newspapers. She cut out the most important stories (domestic issues, international crises, anything about the president), made photocopies and delivered the packets all across the West Wing. Then she would leave the White House and start her day as an entry-level researcher.

This grunt work eventually scored her a staff position with Deputy White House Counsel Bruce Lindsey, an Arkansas lawyer who had followed Bill Clinton to Washington, and served as the unofficial “traveling chief of staff,” as O’Leary put it. Lindsey went everywhere with the president, and with all that travel, he needed an assistant who could be his eyes and ears in Washington. Remembering the initial job offer, O’Leary said she was supposed to attend internal White House meetings, write memos and brief Lindsey on whatever he had missed while away. It would have been a great job, she said, if she hadn’t started in 1994, when the House of Representatives launched the Whitewater investigations. Lindsey, who had known the Clintons for over 20 years at this point, was named a “likely co-conspirator” and excluded from most cabinet or committee meetings. O’Leary’s day-to-day life suddenly centered around the Whitewater controversy, and all the related paperwork.

She stuck it out for nearly two years before honing in on her true passion — family and education policy. “In my family, my mom was a social worker [and] my dad was a labor union leader, but most importantly, my sister struggled with mental health issues,” said O’Leary, “[so] I have always been really interested in how we support kids from the earliest age.” 

In 1997, she received her master’s in education policy from Stanford University and quickly returned to the White House as a special assistant reporting to both the Domestic Policy Council and the office of the first lady. When Hillary Clinton decided to run for Daniel Patrick Moynihan’s vacated senate seat, O’Leary once again worked overtime, performing her special assistant duties during the day and volunteering on the campaign at night. Clinton won and she bumped O’Leary up to Senate aide and legislative director. 

At this point, O’Leary had served the Clintons through two bombshell scandals — Whitewater and Monica Lewinsky — and about nine months into the new job, she found herself coordinating the legislative response to 9/11. In 2008 she would volunteer for Clinton’s first fruitless campaign for the presidency. 

Among these crises, scandals and disappointments, O’Leary built a reputation as a detail-oriented policy analyst. After earning a law degree from UC Berkeley, she ventured into the nonprofit industry and helped coordinate “Too Small To Fail,” an early childhood development initiative produced by the Clinton Foundation and Next Generation, where O’Leary was serving as vice president. 

Her most recent project was created with the former dean of UC Berkeley Law, Christopher Edley Jr. The pair first met in the final years of the Clinton presidency, when she was working as a special assistant and he worked for  the Office of Management and Budget. They reconnected at Berkeley, where O’Leary later spearheaded several of Edley’s research programs on economic security, health care and education. She approached Edley in late 2014, after leaving Next Generation, to see if he would want to combine research initiatives. Increasingly frustrated by university bureaucracy, but lacking the resources to operate his own independent non-profit, Edley said that O’Leary’s offer gave him confidence that they would have the “critical mass of activity” to create a worthwhile organization. The Opportunity Institute, which aims to improve social mobility by focusing on K-12 education policy, officially launched in August 2015, just a few months after Clinton announced her second run for president. 

According to Edley, O’Leary had planned on taking a leave of absence to help Clinton’s campaign get off the ground. “But she didn’t come back,” he said, laughing. “Literally, Hillary would not let her leave.”

Judging by the Education Weekly and Inside Higher Ed headlines, education advocates were close trackers of O’Leary/Clinton collaborations, and her increasing involvement in the 2016 race indicated to many that Clinton was planning on making issues like access to education and paid family leave a national priority.

With stations like NPR referring to Clinton as the future “Wonk in Chief” and noting how “‘in my plan’ has to be the most oft repeated phrase in her stump speech,” it’s little surprise that her recent campaign valued policy nerds and hyper-specialized expertise. The Brooklyn headquarters even had a “Wonks for the Win” sign dangling from the ceiling. As the three senior policy advisors, O’Leary, Jake Sullivan (who worked with Clinton at the State Department) and Maya Harris (sister of California Senator Kamala Harris and Clintonland newcomer), were the brains of the operation. Sullivan primarily dealt with foreign policy, but also helped with problems like tax reform; O’Leary dealt with a range of domestic and economic policy issues; Harris, according to Sullivan, “handled basically everything else,” including criminal justice and immigration. The campaign’s greater policy staff reported to the trio collectively. 

As a senior policy advisor, O’Leary often worked from the road, crafting legislative responses to city crises (think Flint, MI) and serving as a campaign surrogate. Despite her unpredictable schedule, colleagues described O’Leary as an accessible, hands-on leader. “She’s a born mentor,” said Sullivan. “Every single member of our policy team — it could be interns to more senior folks who reported to us — looked to Ann to learn how to be a better professional and how to be a better person, and she always found time even in the crush of the campaign to be able to work with folks.”

In August, she was appointed co-director of the Clinton-Kaine Transition Project, a job which required her to relocate to D.C., where she would be expanding Clinton’s staff of 50 to 1,000 come November. It was rewarding and exciting work, but it presented plenty of challenges.

One such challenge came in the form of 20,000 pages of email correspondence from campaign chair John Podesta’s personal Gmail account, obtained by the Russia-affiliated hacking group known as Fancy Bear. Throughout October, Wikileaks published the documents in daily installments. Some of the emails revived old controversies surrounding Clinton Foundation donors and Clinton’s cozy relationship with Wall Street bankers. A couple revealed Podesta’s love for a creamy, slow-cooked risotto. Others fueled conspiracy theories. Many reflected the normal, often boring mechanics of developing policy proposals for Washington’s most high-profile policy wonk. 

Sullivan said the daily leaks created a sense of mounting pressure. “In and of itself it was a stressful time,” he said of the campaign’s final days. “Then on top of that stress is the fact that you had a Russian information warfare operation going on against us, and then added on top of that you had the private communication between individual campaign members being spilled out in the press for everyone to see.”

“The confusion and the personal toll it took on us was a huge distraction,” said O’Leary, who appeared 702 times in the leaked Podesta emails. The documents revealed both her personal email and cell phone number to the public. “I had horrible, horrible, horrible messages left on my voicemail,” she said. “I received hundreds and hundreds of emails… [it was] the darkest side of politics and the dirtiest tricks.” 

Despite the chaos, Clinton’s team pushed forward toward what they believed was a certain victory. Their mindset was to keep working, right to the end. 

So O’Leary was working on election day. Paperwork at the D.C. office turned into phone calls on the train to Manhattan, which turned into greeting VIP donors at the Jacob Javits Convention Center, where Clinton supporters gathered under symbolic glass ceilings. “That was a really fun part of the night,” she said. “It was kind of euphoric.”

Then, around 10:30 p.m., things began to take a turn.  O’Leary wasn’t actually with Clinton as she watched state by state go red, but she was texting people who were — “Is it as bad as it looks?” It was, they said.

O’Leary knew what to do if they won, and she knew what to do if they lost (though she hadn’t considered it a possibility until that point), but what would happen, she asked Podesta, if they had a Bush v. Gore situation? What would happen if key states were too close to call, if the campaign demanded a recount? Podesta told her that they would open the transition office and prepare to fight. 

Florida, North Carolina, Utah, Iowa… Throughout the night, O’Leary’s nine-year-old daughter was texting her, worried. In the VIP area, she said she spotted Khizr Khan, the Gold Star father who had criticized Trump at the Democratic National Convention. Looking at his face, O’Leary began to tear up. That was when Marian Wright Edelman, president of the Children’s Defense Fund and the first African American woman admitted to the Mississippi State Bar, took her hand and said, “You can cry tonight, but tomorrow you need to get up and keep fighting.” When Podesta walked out onto the America-shaped stage and told the crowd that it was too close to call, O’Leary booked the 3 a.m. Amtrak back to D.C. She and her colleagues were standing on the Penn Station platform when Trump claimed Wisconsin, achieving the 270 electoral votes needed to win. It was over, but they boarded the train anyway.

It takes three hours to get from New York to D.C., two hours and 50 minutes on a good day. Back at the Paradise Hotel in Manhattan, where Clinton had watched the results, Sullivan said he was working with two speechwriters to draft her conceding remarks. On the train, people talked and texted, drafted Facebook posts and stared out the window. Among them was Karen Dunn, a volunteer debate trainer, who said she knew most of the people on board. “[They] were doing what I was doing, which was to go home and be there when their kids woke up,” she said. “It was a very popular train that night.” 

Like Edley, O’Leary had first met Dunn during her second — and possibly last — stint at the White House, but they became friends while working for Clinton in the Senate soon after. “Ann would do the policy and I would do the communications,” said Dunn. 

According to Dunn, O’Leary has always been a resource for others on the Hill, both professionally and personally. “I’ve seen over the years that people really just gravitate towards her. They trust her, they go to her for advice,” said Dunn. “She is incredibly patient and passionate.”

That night, as they sat together on the ride to D.C., Dunn encouraged O’Leary to think about joining Boies, Schiller & Flexner (BSF), the law firm where she was a partner. O’Leary didn’t consider the suggestion too seriously, since it had been five years since she practiced law, making her an unlikely candidate for any role.

Ultimately, O’Leary returned to California and told her kids that she wasn’t going to be traveling anymore. Yet this was a promise she had to break just one week later, when Clinton called her back to D.C. “She told me that the first thing she was going to do as president was give a speech for the Children’s Defense Fund,” said O’Leary, “and she still wanted to give it, but she needed me to be there.” Even now, these calls are not uncommon. This past month, she received an email from Clinton’s staff asking for help on an upcoming speech. “The thing about Hillary is she is such a good friend,” said O’Leary. “I’ll always do whatever she asks.”

Dunn encouraged O’Leary to come back to the East Coast again just a few weeks later to have dinner with her, David Boies and Jonathan Schiller of Boies, Schiller & Flexner. The firm had been looking to expand not only their Northern California presence, but their range of services as well. They talked for over three hours at that dinner in New York, ultimately convincing her to join the firm’s Palo Alto office as a partner. 

Now O’Leary spends her days helping tech companies with crisis management, advising clients on everything from public perception issues to policy and regulatory conflicts. She also does a lot of pro bono work — in the wake of the #MeToo movement, O’Leary said that the National Women’s Law Center has sought her advice, and last year, she represented a group of administrative law professors fighting the Trump administration’s attempt to cut federal funding for sanctuary cities. 

“I think the process of law has evolved,” Dunn later explained. “I did not think that Ann would come and do garden-variety litigation, but she is brilliant, and she is a recognized leader in her field across numerous policy areas. Everybody that knows Ann respects her a tremendous amount.” 

In a country where only 20 percent of law partners are women (as is the case at BSF), the importance of female networking is not lost on O’Leary — if it hadn’t been for Dunn’s persistence, she said, she wouldn’t be practicing law in the way she does now. And as for the other wonks, Sullivan picked up a teaching gig at Yale and Harris is currently a political analyst for MSNBC. 

For young women looking to follow her lead, or Clinton’s lead, or Harris’ or Dunn’s or Edelman’s, O’Leary has some simple advice: Find your passion and keep at it. 

“Even though this is a huge loss, I have spent more than 20 years fighting for the things I care about, and I have seen major changes in this country,” she said. “We are moving the boulder up the hill.”

Graphic by Carrie Clowers ’18

Graphic by Carrie Clowers ’18