Believer: My Forty Years in Politics (23 page)

During the August 2005 recess, Obama made his first overseas trip as a senator, accompanying Lugar to Russia, Ukraine, and Azerbaijan to inspect large caches of loose chemical, biological, and nuclear weapons that were dangerous relics of the Cold War. It was a prelude to a new arms-control law the two would introduce jointly. On their way back, the delegation had stopped in London when news of Hurricane Katrina reached them. Barack was watching TV in a hotel bar as CNN broadcast the horrific images of the hell on earth that was New Orleans. As the floodwater rose, desperate residents, many of them poor and black, stood on the roofs of their homes waiting for help that never came. “People in that bar were looking at us in complete disbelief,” he reported. “They were floored that negligence on that scale could happen in America.”

When he returned to the States, Obama was besieged by media requests. Everyone was interested in what the most prominent African American officeholder in the country thought about the events in New Orleans and the laggard government response—and Barack felt compelled to weigh in. He was wary of being pigeonholed as a “black politician.” “I am of the black community, but not limited to it,” he would say. Still, he had spent much of his life wrestling with questions of race and identity, and understood the unique place he now held in America’s politics. Given the magnitude of the disaster, he felt a responsibility to speak out forcefully on Katrina. It was suggested that Obama head straight to New Orleans, but when the logistical challenges of such a visit were considered, the idea was quickly dismissed.

Alyssa, Obama’s savvy scheduler, had a better idea. Former president Clinton and Senator Clinton were headed to Houston, where the Astrodome had become a temporary shelter for thousands of refugees. Former president George H. W. Bush would meet up with them there. What if she could wrangle an invitation for Obama to join them? When Obama, who was soliciting relief funds from Illinois companies, called Clinton to discuss the effort, the former president invited him to Houston.

Obama was eager to dive into the Katrina issue, which he found deeply wrenching, but he was careful not to add to the outcry of racism it had provoked. “I don’t think the Bush guys said, ‘Those folks are black so take your time getting there to help,’” he told us before making the trip to Houston. “They just (a) blew it; and (b) have no clue about the state of these inner-city communities, where people don’t have the wherewithal of wealthy folks to pick up, jump into their Range Rovers, and flee.”

As Obama went from cot to cot alongside President Clinton in Houston, warmly ministering to shell-shocked families, George Stephanopoulos was calling Gibbs and begging for Obama to give him an interview. “If you’re ever going to do it, this is the right time,” George said. “People want to hear from him on this.” The decision to appear on the program marked the end of Obama’s self-imposed exile from the Sunday shows.

Katrina was a turning point for Barack. However intent he had been on keeping a low profile, there was no avoiding the spotlight now. Obama was an eloquent and thoughtful bridge after the storm, giving voice to the more enduring crisis—the widening gap between the rich and the poor in America—that it had exposed. “I think the important thing for us now is to recognize that we have situations in America in which race continues to play a part; that class continues to play a part; that people are not availing themselves of the same opportunities, of the same schools, of the same jobs,” he told Stephanopoulos. “And because they’re not, when disaster strikes, it tears the curtain away from these festering problems . . . and black and white, all of us should be concerned to make sure that’s not the kind of America that’s reflected on our television screens.”

 • • • 

In September, Rouse arranged a call between Obama and his inside and outside advisers on the pending nomination of John Roberts to become chief justice of the Supreme Court. The Left was bitterly opposed to Roberts, a politically astute judicial conservative who, at a youthful (by Supreme Court standards) fifty years old, could shape the Court for decades to come. For Obama, it was not an easy decision. Friends had contacted him to vouch for Roberts. Besides, Obama said, “If I become president someday, I don’t want to see my own, qualified nominees for the Court shot down because of ideology.” Interesting, I thought, that he would frame it that way. Gibbs said a vote for Roberts would position Obama more in the political center, which could be advantageous in future races. “Not in a primary,” I replied. We were all talking around it, but national politics had quickly emerged as a subtext of our discussion. Finally, Rouse came down against Roberts, and so, too, did Obama.

“I spent time with Roberts, and came away convinced that he is qualified in every way,” Barack said to us. “He’s obviously bright. He knows his stuff. But I also have this nagging feeling, based on his opinions, that anytime there’s a contest between the powerful and the powerless, he’ll find a way to make sure the powerful win. That’s how he’ll interpret the law. And that’s not my vision of how the courts should work, and particularly not the Supreme Court.” I didn’t think Barack was rationalizing his decision, but I also knew the politics were not lost on him.

The other issue drawing Barack out was Iraq. The situation there was eroding. Public opinion was turning sharply against our involvement, and sentiment for withdrawal of our 160,000 troops was growing. Iraq had become an albatross for those who had supported the war, and the wisdom of Obama’s early opposition seemed clearer by the day. He had kept a low profile on the war during his first months in the Senate, in part because he didn’t want to appear to be showing up Democratic colleagues who had supported it. “Everyone knows where I was on this from the beginning,” he explained. “I think it’s best to be a little low-key for a while.” By late summer, however, Barack’s posture had changed. He felt he couldn’t stay quiet any longer. He and his national security adviser, Mark Lippert, a crew-cutted naval reservist, developed a plan for a “phased withdrawal” of American troops, tied to political and security benchmarks.

Barack unveiled his Iraq proposal in a speech to the Chicago Council on Foreign Relations, where he assailed the absence of a coherent strategy from the Bush administration. Just as with Katrina, though, Barack’s critique of Bush was more nuanced than a raging antiwar screed. Barack’s “phased withdrawal” plan, calling for a significant number of our troops to be out of Iraq by the following year, didn’t please those on the left who favored immediate withdrawal; nor did it captivate those on the right who opposed any withdrawal. Yet it thrust Obama back into the middle of an Iraq debate that was likely to shape the 2008 election.

Between Katrina, Roberts, and Iraq, Barack’s determination to keep a low profile for 2005 went by the boards. The murmurs about 2008 predictably picked up, and a trip he unexpectedly added to his schedule at the end of the year would only fuel the speculation.

Throughout the summer and fall, Senator Bill Nelson of Florida had asked Obama repeatedly to give the keynote address at the state’s Democratic convention in mid-December—and each time, Barack had demurred. It was a weekend speech, and he knew it would mean time away from his family. Besides, he had irritated Michelle by traveling the country several weekends that fall instead of coming home from Washington. So when Gibbs suggested they give the Floridians a definite no, Obama stunned him by replying, “What if I want to go?”

Obama told Gibbs he was eager to “try some themes,” and he thought the Florida event would be a great place to roll them out. Left unspoken, because it needed no amplification, was what Florida had come to mean in national politics. No Democrat would recapture the White House without it, which is why three men who were looking hard at 2008 had signed up to speak there. Edwards, Vilsack, and Governor Mark Warner of Virginia were all eager to flash their chops for thousands of delegates at a Disney World resort. By tapping Barack for the prized keynote, the organizers had spared themselves the dilemma of having to choose among the aspiring candidates. The invitation also reflected the growing curiosity and interest Obama was generating all over the country. What was clear to all of us who worked with Obama was that his unexpected decision to risk Michelle’s ire and go to Florida reflected growing curiosity and interest of his own.

With Barack’s input, Favreau and I worked together on the first of what would be many collaborative efforts in the years to come. Most political speeches today are a series of applause lines, strung together with filler. Barack viewed speeches as carefully constructed arguments. He had learned to animate them with inspiring stories from the lives of people he had encountered, and considered the sound and cadence, as well as the meaning, of words and how they played against one another. Favreau, an accomplished musician as well as a gifted young writer, was innately attuned to the rhythms of language. He and Obama were a perfect match, and the Florida speech was a moving—and suggestive—composition, recalling the themes that animated Obama’s maiden voyage on the national stage in Boston.

“We’re tired of being divided, tired of running into ideological walls and partisan roadblocks, tired of appeals to our worst instincts and greatest fears,” he thundered. “Americans everywhere are desperate for leadership. They are longing for direction. And they want to believe again.”

Obama flew back home the same night, leaving a huge buzz of “believers,” and a few deflated presidential aspirants, in his wake.

“They may not be able to pronounce his name, but Florida Democrats sure love Barack Obama,” wrote Steve Bousquet in the
St. Petersburg
Times
. “He was introduced to 2,000 party activists as a ‘rock star’ Saturday night, and the freshman senator from Illinois lived up to the grandiose billing.”

Barack was just thirteen months removed from the Illinois State Senate and had not yet been in Washington for a full year. A 2008 campaign for president still seemed ludicrous and remote. Yet clearly things were changing. It would be easy to ascribe it all to some unseen hand pushing this audacious idea along. Still, it was impossible to miss that one of the hidden hands steering events belonged to the man himself, who continued to say no even as his body language now said, “Maybe.”

Attuned to these developments and the shifting political tide, Rouse sent me a memo he wanted to share with Obama. In it, he advised that if there were even a small chance that Barack might change his mind and run in 2008, we should build out his travel in 2006 to include meetings at every stop with influential locals who could be useful down the line.

I agreed with Rouse and the team that this was the way to proceed, and we sent the memo. Barack quickly returned it with a three-word note in the margin that spoke volumes:

“This makes sense.”

J
UST
A
FEW
DAYS
into 2006,
O
bama set out for his first trip to a country half a world away that was playing an increasingly prominent role in his political story.

Three years earlier, he had warned against an invasion of Iraq. Now he and a group of congressional colleagues headed there to assess the efficacy of the war effort. Nothing Barack saw on the ground allayed the concerns he had expressed from the start. With the dictator Saddam Hussein gone, the historic rivalries between Sunni, Shia, and Kurd that he had subdued by force were reemerging with a vengeance, challenging the prospects for a viable democratic state.

“It was just what I was afraid would happen,” Barack said to me later. “We can send all the troops we want. But if these sectarian factions can’t come to a political settlement, we’re just spinning our wheels over there—and at a hell of a cost. We’re trying to build a house on a bed of sand. It needs a better foundation if it’s going to stand.”

When he returned, he sat with Russert on
Meet the Press
to discuss his findings. Praising the heroism of our troops, Obama argued for the need to phase down our involvement while increasing incentives for reconciliation. Before he could escape the chair, the dogged host pushed Obama again on his political plans. Confronting Barack with a
Tribune
article assessing his first year in the Senate, Russert noted that Obama had used more ambiguous language than his unequivocal disavowal on the same show a year earlier.

“There seems to be an evolution in your thinking,” the host said. “This is what you told the
Chicago
Tribune
last month: ‘Have you ruled out running for another office before your term is up?’ Obama answer: ‘It’s not something I anticipate doing.’ But when we talked back in November of ’04 after your election I said, ‘There’s been enormous speculation about your political future. Will you serve your six-year term as United States senator from Illinois?’ Obama: ‘Absolutely.’”

Barack shook off the question.

“I will serve out my full six-year term. You know, Tim, if you get asked enough, sooner or later you get weary and you start looking for new ways of saying things,” he replied. “But my thinking has not changed.”

So you will not run for president or vice president in 2008?

“I will not,” Obama said.

Yet things
had
changed, and even as he gave Russert another firm no, Barack was positioning himself to seize the moment if and when it came. He had in hand the memo Rouse, Gibbs, and I had sent outlining a program in 2006 that would keep his options open for 2008.

“If making a run in 2008 is at all a possibility, no matter how remote,” we had written, “it makes sense to begin talking and making decisions about what you should be doing ‘below the radar’ in 2006 to maximize your ability to get out in front of this presidential wave should it emerge and should you and your family decide it is worth riding.” We had offered him an opt out, and he had driven right through it, authorizing a series of activities aimed at subtly nurturing the possibility of a candidacy.

Obama already had committed to aggressive travel in 2006 to raise money and build support for Democratic Senate candidates, a strategy designed to burnish his reputation as a “team player” within the caucus and earn chits with his colleagues. Now we set in motion our plan to expand Barack’s trips to include meetings with key political players, donors, and local media. We also moved to enhance his political and policy teams, increase his personal fund-raising goals, and seize timely opportunities to spell out an alternative vision for the Democratic Party.

I was skeptical. Hillary was vacuuming up dollars and political commitments, and many other potential candidates already were barnstorming the country, competing for the meager leavings from her table. Most of all, I doubted that Barack, with a young family, would decide that this was the right time to commit to all the hardships of a presidential candidacy.

For my part, I had a bunch of new projects in 2006 that were more immediate and realer than the remote prospect of an Obama presidential candidacy. One of the most satisfying began with a phone call from an unlikely source: my sister, Joan.

Saint Joan, as we sometimes call her, has always been involved in good deeds. An educational psychologist, she is a hero to families around Boston for the guidance and advocacy she has provided for countless kids with learning disabilities. Yet, save for her days as an antiwar protester in college, Joan was never much of a political activist until she took an interest in town government and school board elections in Arlington, the suburb just northwest of Boston where her family lived. Warm, effusive, and relentless, Joan committed her nights and weekends to the school battles and developed into a master field organizer. Her talents had not escaped the notice of aspiring candidates, and now one had stolen her heart.

“Dave, I never do this,” she said. “But I just met a guy you have to work for. His name is Deval Patrick and he’s running for governor here. I don’t know if he has a chance, but he’s such a good guy. He’s progressive. He’s idealistic. He’s really inspiring. You would love him.”

I knew a little about Patrick and the Massachusetts race. Deval was an African American who had led the Civil Rights Division in the Justice Department during the Clinton years. Friends who had worked with him were effusive in their praise. However, the smart money dismissed Patrick, little known to voters in a state with a relatively small black population, as largely irrelevant to the gubernatorial race. Mitt Romney was retiring after one term to run for president, so, in that sense, the race appeared wide open. Yet Tom Reilly, the state’s attorney general, had a huge leg up on the Democratic nomination. If voters preferred an outsider, another rumored candidate, a venture capitalist and education reformer named Chris Gabrieli, could bring significant personal resources to the race. The Beacon Hill insiders were disdainful of Patrick’s prospects, as the relative unknown spent a great deal of time and money building a grassroots field operation and meeting with local activists like my sister.

Joan’s enthusiastic report on Patrick piqued my interest, and the next day, entirely by coincidence, I got a call from Doug Rubin, a senior adviser for Patrick’s campaign. Rubin didn’t know my sister; his inquiry about whether our firm would take a meeting with Deval had been prompted entirely by our role in the Obama campaign. “This must be kismet,” I told him, relating Joan’s call.

The more I learned of Deval’s compelling story, the more I was drawn to him. He was a native of Chicago’s South Side. His father, Pat, a saxophone player for jazz icon Sun Ra, had abandoned the family, walking out despite the plaintive pleas of his four-year-old son. Deval, his mother, and sister shared a room in his grandparents’ small tenement apartment, where some nights he got to sleep in the bunk bed and other nights he took his turn on the floor. Then Deval’s life took a dramatic turn when a Chicago public school teacher nominated him for a scholarship at the prestigious Milton Academy in Massachusetts. Milton was a world (maybe a couple of worlds) apart from the one into which Deval had been born. He showed up at Milton dressed in a windbreaker because he had been informed that students were required to wear jackets to class. Notwithstanding the culture gap, Deval excelled and won scholarships to Harvard College and then its eminent law school. As a Justice Department official during the Clinton administration, Deval had proved himself a fierce and able advocate for civil rights, sometimes locking horns with the political hands in the White House who preferred a more muted approach. He went on to break through corporate barriers by becoming the chief counsel first for Texaco and then for Coca-Cola.

Obama knew Patrick well through legal circles. “He’s a great guy,” Barack told me. “You’ll really like him. I don’t know what kind of chance he has, though. Seems like a tough road.”

Whatever the odds, once Plouffe and I had traveled to Massachusetts to meet Deval, my desire to do the race was unequivocal. He was genuine, passionate, and inspiring. In Deval’s campaign, I had found another, exhilarating opportunity to tilt at a windmill and break down a barrier.

For all their superficial similarities and shared ideals, Deval and Barack were very different people. Barack, tall, regal, and blessed with a mellifluous baritone, was more reserved and self-possessed. Deval, half a head shorter with a voice several octaves higher, was naturally warm, open, and accessible. Barack made an early commitment to a career in politics. Deval came to it much later, after his government and private-sector career, and there was a charming innocence to his candidacy. Deval cheerfully endorsed gay marriage before it was fashionable, and a proposed wind farm in the waters off the coast of Cape Cod—an irritant to many of the Cape’s prominent denizens, including the revered and powerful senior senator Ted Kennedy. “Look, I believe in these things and I’m going to run on what I believe,” Deval explained to us when some of the prickly issues came up for discussion. “If that costs me the job, I can live with that.”

Deval and I clicked in every way, collaborating on a series of ads, scripted and unscripted, designed to bring his ideals and vision for Massachusetts to life. Like Barack, he was an eloquent and evocative writer, who drafted his own, soaring speeches, including a stem winder he delivered to the state Democratic convention. “It’s time to put our cynicism down,” he implored the delegates. “Put it down. Stand with me and take that leap of faith. Because I’m not asking you to take a chance on me. I’m asking you to take a chance on your own aspirations. Take a chance on hope.”

Take a chance on hope. In times of disillusionment and doubt, it was such a timely and affirming message. In its freshness, authenticity, and idealism, the Deval Patrick campaign was the spiritual twin of the Obama for Senate campaign. Yet, in its execution, the Patrick campaign was far more advanced. It drew an incisive corps of young insurgents, some of whom were refugees from Howard Dean’s failed presidential bid. As such, they had glimpsed the potential of the Internet, and tech-savvy Massachusetts proved to be fertile ground for their new, expansive digital strategies. Plouffe took copious notes that would pay off down the line.

 • • • 

The other big project we took on in 2006 was for Rahm. Nancy Pelosi, vying to become the first woman to serve as Speaker, had drafted Rahm to chair the DCCC and spearhead the party’s effort to recapture the House. Rahm’s legendary fund-raising prowess, shrewd political instincts, and almost pathological competitiveness made him the perfect choice. After a few weeks of playing hard to get, Rahm cut a deal and accepted the DCCC post, which he knew would consume him for two years and take time away from his young family. In return, he demanded a coveted seat on the House Ways and Means Committee and a place on Pelosi’s leadership team if the Dems took back the House.

However reluctant Rahm might have been to take the job, he attacked it with his typical manic energy. He spent months recruiting top-notch candidates in swing districts, love-bombing them with visits, e-mails, and follow-up calls. When Heath Shuler, a former NFL quarterback from western North Carolina, initially refused Rahm’s draft appeal because he worried about being away from his small children, Rahm called him repeatedly from his own family events. “I’m at a soccer game with my kids. Just wanted to let you know that,” Rahm would say, and hang up. “I’m at a kindergarten play now. Talk to you soon,” he’d bark. After ten of these calls, Shuler finally surrendered. Then, after he’d rounded up an all-star slate of challengers, the relentless Rahm spent hours each day overseeing their progress and raising money for an independent campaign to support their candidacies. My firm agreed to help shape strategy and produce party-sponsored ads in a handful of these pivotal districts. As part of the deal, and in a nod to a friendship of more than twenty years’ duration, I threw in therapy calls with Rahm at all hours of the day or night, which I knew I would have received in any case.

We took on one other assignment in 2006 that was a labor of loyalty and love—one that would provoke one of the few angry exchanges I ever had with Barack Obama.

My close friend and former business partner, Forrest Claypool, was rattling one of the few pillars still standing from the old Chicago Democratic machine by challenging a longtime incumbent for president of the Cook County Board of Commissioners, a position second in power only to mayor.

It wasn’t the first time Forrest had shaken things up. When Daley appointed him to head the Chicago Park District in 1993, Forrest slashed a bloated bureaucracy, fired politically connected slackers, and used the proceeds to enrich park programs. Daley saw the parks as vital civic assets and neighborhood anchors, and tolerated Forrest’s reforms despite wails of discontent from patronage-hungry ward committeemen. Then, in 2001, when Forrest decided to challenge a veteran ward heeler with ties to the Daley family for a seat on the county board, the mayor fought unsuccessfully to stop him.

Now, after four years as a reform voice on the board, Forrest was challenging one of Daley’s longtime African American allies, John Stroger, for county board president. Forrest saw it as a chance to reform another bloated, underperforming government body. Yet the mayor and his organization were hell-bent on defending their man. Yes, Stroger, seventy-six, was well past his prime, and his prime wasn’t all that impressive, but he had earned their fidelity with his own, having supported young Rich Daley for mayor over Harold Washington—the only black ward committeeman to do so—just as he would back Dan Hynes over Obama in the Senate primary two decades later.

I respected Daley and valued our relationship, but I also believed deeply in Forrest, his passion and integrity. I knew the difference he could make to fix an antiquated, corrupt system that, among its other responsibilities, administered the county’s health care system for the poor. If he succeeded there, he would be well positioned for higher office in the future. So I worked pro bono for his insurgent campaign, and Forrest slowly gained momentum—with the support of the local newspapers, government reform groups, and a few politicians like Rahm who were willing to buck City Hall. Still, there was one endorsement I felt could make the difference.