Since launching “Cape Up” last August, I’ve not only introduced you to senior people in the Obama administration, but I’ve also tried to transform those bold-faced names into real people with heart and stories to tell. So, on this final day of the Obama presidency, I hope you will indulge one more trip down memory lane as some of the people who had a front-row seat in a historic administration share their hardest moments and revel in the experience of serving their country.

Valerie Jarrett, Senior adviser to President Obama since 2009
Key moment: Shooting at Sandy Hook Elementary School in Newtown, Conn.


I remember being in the Oval Office when the president heard that there were 20 children and six adults, and I couldn’t process the number 20. And then, right after the number was their ages. And to think about 6- and 7-year-olds, I was in shock and of course I think everyone’s first reaction is, you think about your own loved ones and the phone calls that the parents were receiving over the media and directly from the school to come to the facility they had available. And then two days later, just two days later, I accompanied the president to Newtown where he greeted so many of the families and delivered an extraordinarily poignant remarks at a memorial service. And I walked around with him, family by family, and some of those families have become very close friends of mine to this day. But to see people on the worst day of their life mourning a child is just excruciating.

Sadly, he has far too many times been the mourner-in-chief. I remember when he went to Tucson right after former congresswoman Gabby Giffords was shot and he spoke about the young girl that was killed that day and that moved him to tears. And I’ve been with him to Orlando. I’ve been with him all over our country. I accompanied the first lady to the funeral of Hadiya Pendleton in Chicago just a mile from where we both live, and she’d just been here a few weeks earlier, marching in the inaugural parade. And so, each one of the lives that have been lost, either through mass casualty or day by day on the streets of my hometown.

Valerie Jarrett (Mandel Ngan/Agence France-Presse via Getty Images)

[Charleston,S.C.,] was very different than Newtown because I think it was a moment where people in our country who didn’t understand or have any exposure to the black church learned something about the spirit of openness, the door welcoming a stranger. And the service was inspirational and uplifting, and the families and their willingness to be forgiving was just such a teaching moment. But Newtown had none of that. Newtown was simply tragic.

It’s hard, and you do have to dig deep, and you have to put your own sorrow aside a bit but yet, allow it in sufficiently that people understand you feel empathy for them. And so it takes strength to feel empathetic and want to just stand there and cry your heart out, but know that you have to be strong so someone can cry on your shoulders. It’s very hard, and the president is very good at it. And of course it takes its toll on him, but that’s part of the job. And it’s the part of the job that I think the American people have every right to expect their president to do, and to do well.

Derek Chollet, assistant secretary of defense for international security affairs (2012-2015) and special assistant to the president and senior director for strategic planning, National Security Council staff (2011-2012)
Key moment: The “red line” in Syria


I was serving at the Pentagon in August of 2012 when Obama uttered the “red line” for the first time in an answer to a question by Chuck Todd, posed to him at a White House press conference. And then in August 2013 is when Bashar al-Assad used chemical weapons and the red line was crossed and we were confronted with what to do about it. And my job at the Pentagon, at the time, was to help plan for the strikes, try to get other countries to contribute their capability to conduct air strikes, unfortunately only one was willing to step up at the time, that was France. … And what ended up happening was something that none of us expected, or really imagined possible, to be honest, which was an agreement brokered in part by the Russians with the Syrians to remove peacefully 1,300 tons of their declared chemical weapons, actually chemical weapons that they had not declared prior to that point.

There’s no question that when it comes to the critique of Obama’s foreign policy this red-line episode is at the epicenter of the critique. But when I think back in terms of our recent history, in Iraq, the United States went to war in the early 2000s to deal with a weapons of mass destruction threat that turned out not to exist. And we’re still dealing with the strategic consequences of that decision today. In Syria, in this red-line episode, the United States did not use force and ended up dealing with a weapon of mass destruction that did exist and was in fact far worse than the CIA wrongly estimated the Iraq threat to be. And yet, that’s seen as a strategic failure.

Derek Chollet (German Marshall Fund)

I don’t see how getting Syria to get rid of 1,300 tons of chemical weapons peacefully shows that we’re weak. My view at the time was that’s what great powers do actually — you get people to do things without having to use force. And also, by the way, remember it was the threat of force, and the build-up to these air strikes, that caused the Russians to come in, at the last minute to say “Let’s try to cut a deal here,” and I think brought Assad to heel.

In fact, it’s interesting if you think about it, and this is one of the reasons why I think this red-line episode is seen as a blight on the president is because it was improvisational. Really from start to finish, it was improvised. The original utterance of the red line was an answer to a hypothetical question posed to the president by Chuck Todd. ‘What would you do if chemical weapons got on the loose, and we thought he was gonna use them?’ Or what-not. And then that’s how the president answered the question, that would cross the red line. If you think about it, the way out of this situation was Secretary of State John Kerry, in the build-up to the use of force, was asked the question, “Well is there anything Assad can do that would prevent being bombed?” And Kerry said, “Well of course, he could give up all his chemical weapons.” But he’s never gonna do that. Phone rings, the Russians say, “Let’s try this.” We’re off to the races.

Susan Rice, national security adviser since 2013, ambassador to the United Nations from 2009-2013
Key moment: 2012 attack on U.S. embassy in Benghazi, Libya


I was asked by the White House, when I was then the ambassador to the United Nations, if I would appear on the Sunday shows and represent the administration, as I’d done many times in the past and done many times subsequently. The news of the week, as people tend to forget now, was not only Benghazi, it was the attacks around the world on our diplomatic facilities from Africa to Afghanistan to parts of Asia. And that was a substantial part of the context, and so was the fact that in the coming days, the U.N. General Assembly, the annual gathering of heads of state, was about to occur. So I was on these shows talking about the attacks on the embassies, Benghazi, Iran and [Israeli] Prime Minister [Benjamin] Netanyahu’s upcoming visit to the United States.

And I was asked about Benghazi, and I gave, as I said at the time, the best information that the U.S. intelligence community had at the time. I said that it was liable to change, that this was our best current assessment. And, I guess, if I have any regrets, I might, in retrospect, have taken my mother’s advice and not gone on the Sunday shows.

Susan Rice (Evan Vucci/Associated Press)

But the fact of the matter is, and all of the investigations have validated this, that the intelligence communities produced points. They were their best understanding of what had happened at the time. I was careful to say that this was preliminary and could change, and indeed some days after I went on the Sunday shows, their assessment did change. But at the time, that was what we could say. And sometimes people have asked why didn’t I insert my own opinion or judgment into what had happened, and my answer to that is that, “It would have been completely inappropriate for me to make up my own judgment and share it on the fly if it was in contravention of what our experts had at that point determined.”

Broderick Johnson, assistant to the president and White House Cabinet secretary since 2014
Key moment: The killing of Trayvon Martin


I’d had conversations with him before Trayvon Martin about what could he do as president to use his bully pulpit and his convening power, and his power and authority as president over federal agencies to really move the needle and to start to do something more transformative to affect the lives of boys and young men of color, brown and black boys especially. So we had talked about those things certainly over time and shared those concerns as two African American men who grew up in the same time under similar circumstances. Had many friends along the way and family members who perhaps hadn’t made it certainly to the kind of pinnacles of opportunity that we had, his being the ultimate want to being president. But for me to be able to do things that I’ve been able to do. But without question, when Trayvon Martin was killed and then there was a trial, it was at that moment he decided I need to do this and do this now. So that was certainly a pivotal moment, but he’d been thinking about these things for a while.

The Civil Rights Act was signed in the East Room of the White House on July 2, 1964, and that was to eliminate the de jure racism. And then we would go from there to have opportunities created, and now over 50 years, how much progress has been created? Well some clearly, but these very stubborn disparities have existed for a set … for decades since then. So the symbolism is almost 50 years to the day the president stood in the East Room of the White House and signed the presidential memorandum establishing My Brother’s Keeper. To really build on the opportunity promise of the 1964 Civil Rights Act and to also tear down the barriers that have existed and to do it in a different way than has been done before. Comprehensive, focused on data and evidence to have stakeholders get engaged in ways that they had not been engaged before public and private.

Broderick Johnson (Jonathan Capehart/The Washington Post)

The fact that it was almost 50 years to the day, is something. You just see the two images of ’64 and 2014 and say, “Wow! How did it happen that it was 50 years and under this president that MBK came to be?” And it wasn’t like we planned it to happen in the 50th anniversary year of the ’64 Act. But as I reflect on it, it’s pretty quite symbolic. Second, there was a substance of it, and that’s a point about how do we make sure these opportunities and these barriers get more systematically addressed because we’ve had so many years of starts and stops or movements or efforts that weren’t so effective? So I think it just goes to so much about the vision and timing of this president.

Fred Hochberg, chairman of the Export-Import Bank since 2009
Key experience: Serving as an openly gay official from the Clinton administration to the Obama administration


JC: Being openly gay in the federal government has changed light-years from even the time you were the deputy administrator in the Bill Clinton administration, even to right now. Talk about that.

Hochberg: Well, I think when I went through Senate confirmation in 1997, 1998, I was held up for seven months. And it was not put in the press, but it was openly discussed. “Well, he’s a gay candidate, and I don’t know if we wanna do that.” So, I think that there were clearly sidebar conversations that came back to me that that was a factor in the delay of my confirmation. Certainly it was a factor in Jim Hormel’s, who was never confirmed as ambassador…

JC: Ambassador of Luxembourg.

Hochberg: Recess appointment. And that’s changed enormously under President Obama, and we have many, many people at all levels of government. We have the secretary of the army, openly gay man.

JC: Eric Fanning.

Hochberg: It’s unimaginable. At one point Eric Fanning, we have six or seven openly gay ambassadors have been appointed by President Obama. And a number of career, openly gay and lesbian ambassadors, people at the department, at the Ex-Im Bank, at agency after agency throughout the government. So, I think that president Obama has always wanted an administration that reflected America in gender and race and religion and sexual orientation. And I’ve been very proud to be a part of that.

Fred Hochberg (Jeffrey MacMillan )

JC: So, when you travel around, you’re an openly gay federal official and you’re traveling around the world. Clearly, they’ve got the Google all over so people can easily look you up and find out your history and your story. Have you noticed or experienced any kind of homophobia when you’re doing your official duties?

Hochberg: Mostly what I like to think is that all of President Obama’s team has really been able to help change that view of what it is to be an American. And when I travel, as part of my goal, even I was in Pakistan recently and I met with the LGBT community in Pakistan. The U.S. embassy set that up. Both Secretary [Hillary] Clinton and followed by Secretary Kerry at the State Department have been very supportive in saying human rights are LGBT rights, and they’re one and the same, and we need to make that part of our stand when we’re overseas. So, I have gone out of my way to particularly meet a lot of women entrepreneurs in those countries, which frequently don’t have the same opportunity as they have in our country. And I’ve met with a lot of number of LGBT business people and activists in those countries ’cause I wanna make sure they have a voice as well. … I’ve met with people in the [LGBT] community in Mozambique and South Africa, and a number of places in Latin America, as I said Pakistan, India. And I think it’s important that as Americans and as gay people, we support brothers and sisters around the world.

Wendy Sherman, ambassador and undersecretary of state for political affairs 2011-2015. Lead negotiator of the Iran nuclear agreement.
Key experience: Serving one’s country as a woman on the international stage.


I learned a long time ago as a woman diplomat myself that when I sit at a table, I don’t sit there as Wendy Sherman. I don’t sit there as a woman. I don’t sit there as a mother or a grandmother or a Jewish American. I sit there as the United States of America. I was the lead negotiator with Iran. There were no women in the Iranian delegation. I spent a good deal of time with them and they understood who I was, what I was, what my background was. But I was the United States of America…..

Wendy Sherman (Charles Dharapak/Associated Press)

It’s a great privilege. It’s a great responsibility. When you sit at the table, Madeleine Albright, who’s just a dear friend and colleague, when she was at the United Nations taught me this profound notion that you are the United States. And the United States has enormous power. So, you have to understand the power the United States brings to the table. Use it wisely for our national security. And understand your responsibility is to do what is necessary to protect the security of our country. And that’s really your only responsibility and, of course, the hardest responsibility.

“Cape Up” is Jonathan’s weekly podcast talking to key figures behind the news and our culture. Subscribe on iTunes, Stitcher or wherever else you listen to podcasts.

President Obama delivered his farewell address to the nation at McCormick Place in Chicago on Tuesday. (Victoria Walker/The Washington Post)