Obama- An Oral History Read online

  Special Envoy for Climate Change, US Department of State (2016–2017)

  David Plouffe

  Campaign Manager, Obama for America (2007–2008)

  Senior Advisor to the President, White House (2011–2013)

  Jen Psaki

  Deputy Communications Director, White House (2009–2011)

  Traveling Press Secretary and Senior Advisor, Obama for America (2012)

  Spokesperson, US Department of State (2013–2015)

  Communications Director, White House (2015–2017)

  Steven Rattner

  Lead Advisor, Presidential Task Force on the Auto Industry (2009)

  Margaret Richardson

  Counselor to the Attorney General, US Department of Justice (2009–2011)

  Deputy Chief of Staff to the Attorney General, US Department of Justice (2011–2012)

  Chief of Staff to the Attorney General, US Department of Justice (2012–2015)

  Dennis Ross

  Senior Director for the Central Region, National Security Council, White House (2009–2011)

  Kori Schulman

  Deputy Chief Digital Officer, Office of Digital Strategy, White House (2009–2017)

  Allyson Schwartz

  D-Pennsylvania, Thirteenth District, US House of Representatives (2005–2015)

  Dan Shapiro

  Senior Director for the Middle East and North Africa, National Security Council, White House (2009)

  Ambassador to Israel, US Department of State (2011–2017)

  Nick Shapiro

  Assistant Press Secretary, White House (2009–2011)

  Senior Advisor to the Assistant to the President for Homeland Security and Counterterrorism, White House (2011–2013)

  Deputy Chief of Staff, Central Intelligence Agency (2013–2015)

  Wendy Sherman

  Under Secretary of State for Political Affairs, US Department of State (2011–2015)

  Acting Deputy Secretary of State, US Department of State (2014–2015)

  Ed Silverman

  Staff Director, US Senate Committee on Banking, Housing, and Urban Affairs (2009–2011)

  Pete Souza

  Chief Official White House Photographer (2009–2017)

  Gene Sperling

  Director, National Economic Council, White House (1996–2001)

  Counselor to the US Secretary of the Treasury (2009–2010)

  Director, National Economic Council, White House (2011–2014)

  Michael Steel

  Press Secretary, House Republican Leader John Boehner (2008–2009)

  Press Secretary, Speaker of the House John Boehner (2011–2015)

  Press Secretary, Vice-Presidential Candidate Paul Ryan (2012)

  Stuart Stevens

  Chief Strategist, Romney-Ryan 2012

  Todd Stern

  Special Envoy for Climate Change, US Department of State (2009–2016)

  Michael Strautmanis

  Chief Counsel and Deputy Chief of Staff, US Senator Barack Obama (2005–2008)

  Office of Governmental Affairs and Public Engagement, White House (2009–2011)

  Counselor for Strategic Engagement, White House (2010–2013)

  Mona Sutphen

  Member, National Security Council, White House (1991–2000)

  Deputy Chief of Staff for Policy, White House (2009–2011)

  Terry Szuplat

  Presidential Speechwriter, White House (2009–2017)

  John Tanner

  D-Tennessee, Eighth District, US House of Representatives (1989–2011)

  Trevor Timm

  Executive Director, Freedom of the Press Foundation (2012– )

  Chris Van Hollen

  D-Maryland, Eighth District, US House of Representatives (2003–2017)

  D-Maryland, US Senate (2017– )

  Tom Vilsack

  Governor of Iowa (D) (1999–2007)

  US Secretary of Agriculture (2009–2017)

  Jeff Weaver

  Campaign Manager, Bernie Sanders for President, 2016

  Frank Wolf

  R-Virginia, Tenth District, US House of Representatives (1981–2015)

  Herbie Ziskend

  Policy Advisor, Office of the Vice President (2009–2011)

  2004–2007

  As an Illinois state senator serving at the turn of the millennium, Barack Obama gave speeches to the types of crowds one would imagine turning out to watch their state senators. “I invited him to come down and speak,” recalled Kareem Dale, who extended his invitation via a student association at the University of Illinois law school. “We probably had about five or ten people in this big, two-hundred-person auditorium. Nobody came. They didn’t know him at all.”

  Yet improbably, one of the state senator’s public appearances helped set the table for a successful US Senate bid and, of course, the presidency. Only thirteen seconds of known footage exists of Obama’s remarks during a lunchtime rally at Chicago’s Federal Plaza. It was October 2002, and George W. Bush was ramping up his ill-fated Iraq War; in Washington, leaders from both parties were largely supportive, but in cities across the country, voices of opposition were rising. At the Chicago rally, signage read “War Is Not An Option” and “Don’t Get Bush No Blank Check.” The headliner was the elder Jesse Jackson, the famed civil rights leader and a Chicago fixture.

  Obama, then forty-one, was in the early stages of a two-year campaign to reach Capitol Hill. Already he had racked up $10,000 in debt from a failed primary race for US Congress two years prior, to say nothing of the student loans from Harvard Law School that he and his wife, Michelle, carried. His 1995 memoir, Dreams from My Father, was greeted with encouraging reviews and discouraging sales—the fate of many a gifted writer. The couple also had two daughters, aged one and four. Political consultant David Axelrod, who was then counseling Obama in an unofficial capacity, once wrote about a conversation around that time in which the candidate feared that if this campaign failed, he would “have to go out and make a living.”

  On a conference call three days before the Iraq rally, an advisor had warned Obama to soften his criticisms—after all, the majority of Washington supported Bush’s hawkish agenda. Obama was unswayed. Transcripts from crude audio show Obama targeting “the armchair weekend warriors” who were devising “a dumb war” and “a rash war” in the Middle East, “a war based not on reason but on passion, not on principle but on politics.” While “under no illusions” about the Iraqi president’s slaughtering of his own people, Obama affirmed his belief that working with the United Nations to contain Saddam Hussein would result in sending him “the way of all petty dictators”—directly “into the dustbin of history.”

  After his speech, Obama retreated to his campaign office on South Michigan Avenue. (TV crews swarmed around Jesse Jackson.) Of course, Washington’s elite did not exactly follow the wisdom of the young state senator—soon the war buildup began in earnest, with approval from Congress, the media, and big swaths of a bloodthirsty public. The local Daily Herald managed to squeeze the “dumb war” line from the speech into its coverage of the Chicago event. It was attributed to “Barak Obama.”

  Two years later, after the 2004 Democratic National Convention in Boston, newspapers would begin to spell his name correctly.

  REGGIE LOVE

  Special Assistant and Personal Aide to the President, White House (2009–2011)

  I had read Dreams from My Father and obviously seen the speech he had given at the convention in ’04. I think he was more concerned with the idea of trying to make our country a better place for as many people as possible than the idea of just becoming a US senator.

  JOSH LIPSKY

  Staff Assistant and Associate Director of Press Advance, White House (2009–2011)

  Special Advisor to the Under Secretary of State, US Department of State (2015–2017)

  I was a credentials checker at the convention, which was like one of those people who stood outside the door making sure people had the right ba
dges. It was a great gig, because then I got to sneak into the hall myself. I had a friend who told me, “You should watch out for this state senator, he’s gonna keynote at the convention, and if you could get his autograph for me, that’d be awesome.”

  REGGIE LOVE

  Issues that were really important to me were also important to him around equality of rights and the ability for people to have access to health care and education. A fifth-grade education in Alabama was significantly different than a fifth-grade education in New York. He saw that and understood that.

  JOSH LIPSKY

  I saw him backstage and went up to him. “Senator, my friend’s a big fan of yours. Could I get your autograph?” And he said, “Sure.” Then he asked, “Do you want one, too?” And I ruefully remember saying, “Oh, no. I’m good. Thanks.” He just wasn’t on my radar at that time. There were so many other things at that convention, and then of course the speech . . . You know the whole history from there.

  ERIC LESSER

  Special Assistant to the Senior Advisor, White House (2009–2011)

  D-Massachusetts, State Senate (2015– )

  I was an unpaid intern for CNN that summer and went with the CNN team as a runner, to work at the convention in Boston. I was from Massachusetts, so it was easy. I just stayed with friends and made it work. And I remember I was in the hall when he gave the speech, and I was really kind of mesmerized by it.

  DARIENNE PAGE

  West Wing Receptionist, White House (2009–2010)

  Director, Veterans, Wounded Warriors, and Military Families Outreach, Office of Public Engagement, White House (2010–2013)

  That convention speech pulled together everything I believed in. That you don’t have to be a Democrat to be a patriot, or a Republican to be a patriot. We’re all Americans. We all love this country. That’s what I saw in my military service. It wasn’t “everybody’s a Republican” or “everybody’s black or white.” It was this melting pot.

  ERIC LESSER

  Every night, at the end of the convention, we’d pick up all the trash and grab all the excess banners to get ready for the next morning. You know how everyone raises their rally banners in the crowd with the names of the people? “Kerry-Edwards ’04” signs would go up. “Max Cleland” signs would go up or whatever. Usually they’d all get thrown on the ground, and everyone would go home. But when I ran out to do the nightly cleanup after Obama’s speech, not a single Obama sign could be found anywhere. Everybody knew they had just seen something historic.

  TOM DASCHLE

  D-South Dakota, US Senate (1987–2005)

  Senate Majority Leader (2001–2003); Senate Minority Leader (2003–2005)

  I got to know Barack in the 2002, 2003 timeframe. As [Senate Democratic] leader, I had to go to Chicago frequently and made it a point to get to know Barack. I was impressed with his oratory. We bonded very early on, and I encouraged him to run [for Senate], and he came out of it very well. I lost and he won. I had a lot of unemployed former staff, including Pete Rouse [and] Denis McDonough. Probably about a dozen members of my staff went to work for him. And so as a result of having so many of my staff there, I felt even more invested in his early years in the Senate.

  JOE LIEBERMAN

  D-Connecticut, US Senate (1989–2006)

  I-Connecticut, US Senate (2006–2013)

  There was a program in the Senate to try and encourage, would you believe, more bipartisanship, and one of the ways that somebody could conceive to do that was to ask each incoming senator to choose two mentors, one Republican and one Democrat. Senator Obama chose George Voinovich, Republican of Ohio, and me to be his mentors. And I must say I was both fascinated and, in some sense, flattered. George and I invited Senator Obama to lunch in the Senate Dining Room. We had a really good talk—just about what it’s like to be in the Senate and why it’s important to try to work across party lines. And I said to George as we walked away, “I don’t think this new senator is going to need a lot of mentoring.”

  TOM DASCHLE

  So when he was deciding to run for president, at one point I counseled him. If I’m any indication, sometimes the windows of opportunity open unexpectedly, and I also have long felt that the longer you’re in Washington, the less valuable you are nationally, because of people’s frustration and cynicism about politics generally. And so I encouraged him to run early in his career rather than run later, because I thought he would be more viable as a candidate without a long record. And he chose to take that advice. I’m sure many people gave it to him.

  JOE LIEBERMAN

  At the end of ’06, Senator Obama said he’d like to come to the office to talk to me. “I’m thinking of running for president for the Democratic nomination and wanted to get your advice.” I said that I thought it was wide open. I thought that the odds were probably against him, but who knew? Sometimes, fate and opportunity strike. It was already evident that Hillary was going to run, but I said, “I’ve done things like this in my own career. I ran for the Senate thinking I had a chance to win. Otherwise I wouldn’t have done it.” Obviously, I’m not the reason he ran, but that was a fascinating discussion.

  LUIS GUTIÉRREZ

  D-Illinois, Fourth District, US House of Representatives (1993– )

  December of 2006, he called me up: “Can you come down to the office, Luis?” And basically the gist of the conversation was I’m going to Hawaii, and when I come back I will have decided whether I’m running for president. He didn’t really let me say much. He said, “And I know what you want.” Just like that. “You want immigration reform,” he said. “We’re gonna do it right away. It’s going to be a top priority, and you’re going to lead on it.” That was maybe a twenty-five-minute conversation, but what-the-fuck did I think he was going to become president? He was just, like, my favorite senator, right?

  JACKIE NORRIS

  Iowa State Director, Obama for America (2007–2008)

  Chief of Staff to the First Lady, White House (2009)

  I was invited to meet with Mrs. Obama, and I was pretty honest in saying, “Look, I’ve got three kids.” At that point they all were under three, I think. “I’m happy to talk to her about the Iowa caucuses and share my experiences, but I am not doing this long term. I’m teaching.” And I had a fabulous meeting. We hit it off. I really appreciated her intellectual grasp and desire to know about the Iowa process, and I came back and I was recalling this story to my classroom. One of my students said to me, “You’re always telling us to stand up and fight for what you believe in. What the heck are you doing?” So I turned around the next day and said, “Okay, I’ll do it.” And that’s how I came on as a senior advisor to the campaign, well before announcement time.

  REGGIE LOVE

  Aside from being the only African American in the Senate, he was, especially when he was running for president, promoted as . . . the one who would help bridge the divide between the Right and the Left. Racial tensions weren’t in the headlines back then, so that wasn’t the focus. It was antiwar.

  HERBIE ZISKEND

  Policy Advisor, Office of the Vice President (2009–2011)

  I was sitting in my apartment in Ithaca in February of ’07 when I watched the announcement from Springfield. I was captivated. I wanted to get involved. I didn’t know anybody. My mom and dad didn’t work in politics [or] know anyone in politics, so I drove my twenty-year-old car to New Hampshire, a six-hour ride. I basically just showed up. They gave me spreadsheets to enter people’s names into, and I was just sitting in the corner of a mostly empty office in Manchester. I ended up skipping a bunch of school my senior year, traveling across New Hampshire, and helping set up events for Obama.

  TEDDY GOFF

  Director of New Media for Battleground States, Obama for America (2007–2008)

  Digital Director, Obama for America (2011–2012)

  He started running on February 10. I started on the campaign not long after and had a story that was fairly typical of the kids who graduated col
lege in ’06 and ’07. I had been volunteering from my dorm room for the second semester of my senior year. Then I graduated and moved directly to Chicago.

  JOEL BENENSON

  Pollster, Obama-Biden 2008 and Obama-Biden 2012

  Chief Strategist, Clinton-Kaine 2016

  I started polling for him in 2007 in the primaries. I was one of the first people Axelrod called and asked to be part of the team. He said he wanted people with an “insurgent mentality.” I thought it was such a great descriptor. He said because, you know, Senator Obama, at that point, was obviously going to be the insurgent candidate, even within the Democratic Party.

  JEREMY BIRD

  Deputy National Director, Organizing for America (2009–2011)

  National Field Director, Obama for America (2011–2012)

  I had come into politics through community organizing and building grassroots support at the local level. I’d worked on ’04 for Howard Dean and then John Kerry and had basically disavowed presidential campaigns. But when I read Dreams from My Father, about being an organizer on the South Side, it really struck me that that’s the kind of person I wanted in the White House—somebody who understood what it was like to live the American dream, but also understood what it was like to sit down with people who were trying to get asbestos out of their housing projects. So I thought I’d work for him.

  SHOMIK DUTTA

  Mid-Atlantic Finance Director, Obama for America (2006–2008)

  Special Assistant to White House Counsel (2009–2010)

  National Finance Consultant, Obama-Biden 2012

  My pitch to the Obama campaign was, “The Clinton network is going to take all the establishment [donors]. What you need is someone who really understands the mid-Atlantic—the less established donors, the real-estate-developer folks who are not national donors and whom you can build a network from. I’m the guy to do that.” I said that if I raised $5 million in the first month they had to make me a mid-Atlantic finance director. I ended up raising the $5 million and became the shithead twenty-three-year-old who ran the mid-Atlantic, which was pretty exciting.