Not everyone can point to a moment, the exact time and place, when a lifelong passion began. I can.

It was 1960, twelve days before the presidential election. John F. Kennedy, locked in a dead even race with Richard Nixon, was barnstorming the neighborhoods of New York City. And on the afternoon of October 27, he came to mine.

Stuyvesant Town, a forest of redbrick high-rises on Manhattan’s Lower East Side, was built after World War II to house the flood of returning GIs and their families. Now, in the final, frantic days of his campaign, Kennedy had come there to summon a new generation of leadership.

I was, no doubt, a little newer than he had in mind. I was five.
An inspiring woman named Jessie Berry, who all but raised me while my mother was at work, took me to see JFK that day. Jessie, an African American, had come to New York from South Carolina as a young woman during the Great Migration. She had spent her days taking care of other people’s kids, scraping together what she could to help support her own two daughters. Yet she was determined that the future be better, if not for her, then for her children and her grandchildren.

Maybe that’s why she took me to see this promising young leader, a Catholic, whose election would break down a historic barrier. Maybe she saw in him hope for the future. (Looking back, I see that she might also have viewed the outing as a way to occupy her maddeningly hyperactive little charge.)

So when Jessie heard that Kennedy was coming to Stuyvesant Town, and would be just two blocks from my family’s apartment at 622 East Twentieth Street, she took me by the hand and we headed to the rally. There, she sat me on top of a mailbox to give me a better view. From that perch, I watched in awe as Twentieth Street (at that section, a wide boulevard) filled up with people  instead of the usual, ceaseless parade of cars. Near the front of the crowd, close enough to shake hands with the candidate, I spotted my sister, Joan, and her friends heading home from the junior high across First Avenue.

I wasn’t the only young kid in the crowd. Stuyvesant Town and the adjoining Peter Cooper Village were built and designed for young families, with a network of playgrounds on greened, tree-lined campuses. So when JFK came, many mothers turned out, babies in tow, eager to catch a glimpse of the dashing young senator. It was, as the advance people who plan such rallies say, a built-in audience.

They listened in rapt attention as he delivered his call to action.
It was just fifteen years after the end of World War II. Every adult there had endured that ordeal and, before it, the Great Depression. Now a Cold War hovered over their everyday lives, carrying with it the threat of nuclear annihilation. They had played a role in saving the nation, and were accustomed to sacrifice, not the pain-free succor that would become the coin of the realm of future political campaigns.

So Kennedy, himself a war hero, didn’t come bearing lavish promises. In a harbinger of the inaugural address he would deliver three months later, he came with a challenge.

“I don’t run on the presidential program of saying that if I am elected, life will be easy,” Kennedy declared, his voice booming off the surrounding highrise buildings. “I think to be a citizen of the United States in the 1960s is a hazardous occupation. But it is also one that offers challenge and hope, and I believe the choice lies with you on November 8.”

“Whether I am the candidate for the presidency, or president, or stay in the Senate, I regard our obligation not to please you but to serve you, and in my judgment, in 1960, a candidate for the presidency should be willing to give the truth to the people, and the truth is that what we are now doing is not good enough.”

I was too young to understand the full meaning of his speech or the magnitude of the moment. I recovered his words only years later, from one of those online archives no one back then could have imagined. I might not have understood exactly why the crowd cheered when it did, or that Kennedy was desperately seeking votes, locked in what would be one of the closest presidential contests ever. Yet to this five-year-old, the scene was pure magic, electric and important. Though I couldn’t grasp the nuances, I somehow absorbed the larger message: we are the masters of our future, and politics is the means by which we shape it. From that moment on, I was hooked. I wanted to be a part of the action.

Fifty-two years later, on November 5, 2012, I stood at the foot of the stage at another huge, outdoor rally, on the eve of another presidential election. It was 10:00 p.m. in Des Moines. A crowd of twenty thousand stretched from the podium on Locust Street four blocks east toward the glistening gold dome of the Iowa state capitol. They waited for hours, on that chilly November night, to watch President Barack Obama deliver the final speech at the final campaign stop of his political career—and mine.

For Team Obama, it was a homecoming. Four years earlier, Iowans had breathed life into his audacious candidacy for president. Obama had virtually taken up residence there, spending eighty-nine days in the state during the runup to Iowa’s critical, first-in-the-nation presidential caucuses, as he made his case for change. Along the way, he developed strong bonds with the folks he met in countless living rooms, diners, and union halls across the state.

While the pundits and political insiders in Washington were smugly writing him off as a political shooting star, Obama placed his bet on Iowa and the army of idealistic young people who descended upon the state, hell-bent on changing the course of history. And without Iowa’s embrace, his candidacy almost certainly would have died a quick, snowy death. 

Iowa was the beginning of everything. Now, steeled by a thousand battles, Obama had returned there to plead his case, seeking the chance to finish what he had started. He had taken bold and controversial steps to revive a wounded economy, but the work of redeeming an embattled middle class was far from done. He had ended our war in Iraq and, having brought Osama bin Laden and many of Al Qaeda’s leaders to justice, was on the path to ending another war in Afghanistan. Yet it would take a continued commitment to bring those troops home, and the world would only become more complex and challenging. After a lengthy and bruising fight to pass historic health care reform, it would take his next term to implement and undergird it against continuing opposition efforts at subversion and repeal. He felt an urgency to deal with the great, unresolved problems of climate change and immigration reform. And maybe, just maybe, a second, resounding victory would pave the way for more comity and cooperation in Washington, which was the great, unfulfilled promise of his presidency.

A year earlier, following a devastating standoff with Congress over the nation’s debt limit, Obama’s standing with the public had hit a new low. Some polls showed his approval ratings sinking perilously below 40 percent. Trial heats with Mitt Romney, the likely Republican nominee, showed the president running well below the majority he would need to win. Nate Silver, the whiz kid political handicapper who later would win plaudits for accurately calling the outcome of the election, had written a provocative and, for our team, thoroughly depressing magazine piece for the New York Times with a pointed headline: “Is Obama Toast?”

And while Obama remained publicly defiant back then, he was privately resigned to the prospect of defeat. “I’m realistic about this. We have an uphill fight,” he said, during one of our conversations in the dark days of 2011. “Michelle and I have talked about it—about where we would live if we lose. The girls are settled here now, so we really need to think about that.”

But whatever doubts Obama harbored were matched by a preternatural sense of competitiveness. This man hated to lose a game of H-O-R-S-E, much less an election that would define his presidency. So he fought his way back, knowing what defeat would mean for his programs, his legacy, and for the millions of young black Americans for whom his election had opened new vistas. And he believed the stakes for the country were large. Now, seven hours before the first polling places opened out east, he stood inside a security tent in Des Moines, waiting to be introduced to the rapturous crowd and shuffling from foot to foot like an athlete champing at the bit to get into the game. Michelle Obama, who had been crisscrossing the nation on her own, had joined up with her husband for the final stop and was making the introductory remarks onstage.

It had been remarkable to watch Michelle’s evolution, from reluctant conscript in 2007 to a buoyant and beloved campaigner five years later. Thrown out on the campaign trail without adequate staffing or preparation in 2007, she quickly became fodder for the right-wing noise machine, which seized on every opportunity to cast her as the angry, militant black woman behind the affable candidate. Michelle, an accomplished lawyer who had given up her career to make her husband’s dream possible, never expected to become fodder for his opposition. She was stung by the nasty characterizations and skittish about putting herself out there for more abuse.

But over the years, she had made peace, if sometimes an uneasy one, with her role as a public figure, using her platform to promote child nutrition and fitness, the welfare of military families, and other vital causes about which she felt deeply. She had become an extraordinarily evocative speaker as well as a charming and witty guest on late-night talk shows. Still, if the First Lady was willing to put herself out there, she was adamant that her splendid daughters, Malia and Sasha, be shielded from the public stage.

Whenever there was a potential scheduling conflict between her public role and her parental obligations, everyone in the White House knew which priority would win. Anyone brave (or dumb) enough to question that rule invariably emerged with scorched ears.

Buoyed by a deep and abiding belief in her husband, Michelle had become his most effective surrogate and, privately, his fiercest defender. Though she had little direct contact with the White House staff, word would spread quickly if Michelle felt the president had been let down. She could be tough, even on his supporters, sharing her frustration over the frequent friendly fire from the Left that always seems unhappy with any compromise. “I’m tired of all the complaining,” she told a small fund-raising luncheon in New York City a few weeks before the election, upbraiding a group of women who had paid twenty thousand dollars a plate for the privilege. “My husband has worked his heart out to get a lot of things done for this country, up against a bunch of folks on the other side who will do anything to get in the way. So just stop it! He needs your help, not your complaints!”

But now the election was just hours away, and Michelle warmed up the Des Moines crowd with one last impassioned plea for support.

“While we have come so far, we know that there is so much more to do. And what we really, truly know is that we cannot turn back now. We need to keep moving this country forward,” she said. “So that means that we need to re-elect the man who has been fighting for us every single day—my husband, the love of my life, the President of the United States . . . Barack Obama!”

On cue, Obama burst out of the tent and sprinted up a set of stairs onto the makeshift stage and into a warm embrace with his wife.

We tend to idealize political families, but the Obamas deserve any admiration they get. As they stood there together and waved to the crowd, at this last rally of their last campaign, they both understood the many sacrifices that Michelle and the family had endured to make Obama’s career possible.

For twelve years as a state legislator, U.S. senator, and presidential candidate, Obama had spent much of his time away from home. Though he was a doting father who pined for his kids when he was on the road, most of the responsibility for raising them fell to Michelle. Their years in the White House, living above his office, were the first in which Barack could regularly and reliably share dinner with the family and spend time with his girls. Yet the presidency also placed extraordinary constraints on their lives.

Maybe it was that knowledge, or Michelle’s proud words, or the sight of so many old Iowa friends at the end of this long gauntlet, but the normally unflappable president was quickly moved to tears.

“Right behind these bleachers is the building that was home to our Iowa headquarters in 2008,” he said, pointing to a rambling storefront that was, five years earlier, our littered, frenzied nerve center. (Today it’s the pristine headquarters of a New Age church.)

“This was where some of the first young people who joined our campaign set up shop, willing to work for little pay and less sleep because they believed that people who love their country can change it.”

“And when the cynics said we couldn’t, you said ‘Yes, we can!’ ”
The crowd picked up the chant. “Yes, we can!”

“You said, ‘Yes, we can!’—and we did. Against all odds, we did! We didn’t know what challenges would come when we began this journey. We didn’t know how deep the crisis would turn out. But we knew we would get through those challenges the same way this nation always has—with that determined, unconquerable American spirit that says no matter how bad the
storm gets, no matter how tough times are, we’re all in this together. We rise or fall as one nation and as one people.”

“Yes We Can.” It was the tag line I had written for the first TV ad of our first, long-shot campaign together just eight years earlier, when Obama, a largely unknown and seriously underfunded state legislator, set out to win a seat in the U.S. Senate. And it became our mantra when, in 2007, he enlisted millions of Americans to the cause of change.

As Obama spoke almost wistfully about those heady, hopeful days of 2008, they seemed like a distant dream. He had first come to Iowa as an apostle of change. Now it was impossible to ignore how much the intervening years had changed him. His faced lined and his hair flecked with gray, Obama had been tested through four of among the most challenging years any American president has faced, and they had taken their toll. He had major accomplishments to his credit, achievements that would help people and advance the nation.

In his first two years in office, Obama had passed more substantive legislation than any president since Lyndon Johnson. But when, in 2010, he lost the gaudy Democratic majorities he had helped sweep in, progress was hard to find. Washington was more bitterly divided and gridlocked than ever. And, now faced with an implacable Republican opposition in control of the House and numerous enough to tie up the Senate, Obama himself had taken on a more partisan edge. The White House operator called me a few weeks before the election and asked if I was available for the president. When Obama got on the line, I asked him if anyone ever said, “No, I’m not available for the president.” He laughed. “Only John Boehner,” he said. The president had once viewed Boehner as a prospective partner. “He reminds me of a lot of the guys I used to serve with in Springfield,” Obama said, recalling his days as a state senator, when he worked easily across party lines. But that proved to be wishful thinking; the two never found a groove. Boehner would be hemmed in by the Tea Party contingent (who helped propel him to the Speakership in 2011), antigovernment absolutists for whom compromise was tantamount to treason. And Obama, burned too many times, grew increasingly dark about the prospects for reconciliation in Washington.

By denying Obama the collaboration for which he had hoped, the Republican leaders had shrewdly forced him into a partisan corner if he wanted to get anything done. And while the slow recovery and continued economic anxieties presented a challenge to his reelection, the president’s failure to tame Washington and build bipartisan bridges was the most often-stated disappointment among the movable independent voters who had decisively tilted his way in 2008.

So 2012 had to be a different kind of campaign, more modest in its ambitions and more pointed in drawing out the deficiencies of our opponent. In 2008 we had built a once-in-a-generation movement for change. In 2012 we simply ran a very proficient political campaign.

As I stood together with my colleagues, and watched the president’s emotional closing argument in Des Moines, I was tearing up as well. I was proud of Obama and what we had accomplished. I knew this amazing band of ours would never be together again, and I was moved by the sea of people, many with kids on their shoulders, who had come out on this cool election eve. Gazing at young kids on their parents’ shoulders, I was transported back in time. I knew that those kids were me, the wide-eyed little boy on the mailbox. And I felt the same excitement I had that fateful day in Stuyvesant Town more than half a century before.

For all the division, rancor, and tawdriness in our politics, the enduring ritual of Americans coming together to choose their leader and chart their course still moved me—as noble and inspiring to a weathered political warrior as it had been to a five-year-old child in New York City. 

After a lifetime of the rough-and-tumble, I still believed: in politics as a calling; in campaigns as an opportunity to forge the future we imagine; in government as an instrument for that progress.

Throughout those years, I had seen our democracy at its best and its worst. I had represented great men and women who had made me proud of my chosen path, and some who had left me disappointed, appalled, and, worst of all, ashamed. My childhood idealism was more measured and mature, shaped by the realization that even great leaders are human and, therefore, imperfect. I had lived the life I imagined as a little boy. Now this period of it was over.

For just as the president had run his last race, I had run my own. Our decade-long partnership was an impossible act to follow. He was an incomparable client—not perfect by a long shot; but brilliant and honorable and motivated by the best intentions; a good friend and a fellow idealist. I had been spoiled. The thought of starting over with someone new—and almost certainly somebody who would fall short of Obama—was unappealing.

Moreover, after more than 150 campaigns, I had to acknowledge the physical and emotional toll they had taken. Campaigns are at once exhilarating and exhausting. For the campaign “guru” (the driver of the strategy), they require the projection of utter assurance, even as you constantly wrestle with uncertainty. They dominate your life and infiltrate your mind, even when you’re sleeping (which is rare). Wisdom and experience have their place, but campaigns demand the energy and mental acuity of youth.

I had spent a good deal of my life on the campaign trail, as a newspaper reporter and strategist, and two glorious but draining years working twenty feet from the Oval Office at a time of seemingly perpetual crisis. And while I had lived my dreams, my valiant wife, Susan, and our three children had paid a high price. I was often away, even when I was home; too frequently an absentee father, leaving Susan and the family to cope with the impact of our oldest child’s debilitating, lifelong battle with epilepsy.

It was enough. So I knew even before the 2012 campaign began that it would be my last. And I relished every moment—the combat, camaraderie, and satisfaction of, to paraphrase Teddy Roosevelt, spending myself in a worthy cause.

Now, in Des Moines, as the president made his final, fervent appeal, I thought about the many colorful characters, famous and obscure, I had covered as a reporter and conspired with (and against) as a political operative for nearly four decades.

And I thought about Jessie Berry, the wonderful woman, now long gone, who looked after me as a child and took me to see John F. Kennedy that fateful October day. What would she have thought if she knew that the little boy she put on the mailbox to catch a glimpse of the next president would one day work twenty feet from the Oval Office? Twenty feet from the Oval Office where a black man sat as president of the United States.

In 1960, in South Carolina, where Jessie was born and raised, the Negro’s right to vote was still being contested by literacy tests and white-robed mobs. This was the withering reality from which she fled.

How would she have felt if she had stood with me now, watching President Barack Obama make his case for reelection?

The half century between the campaign rallies that bracket my life has been one of revolutionary change—changes in our society; changes in our politics and our campaigns, the way they are waged and the way they are covered; changes both in government and in public attitudes toward it, as the boundless faith of the postwar years has often surrendered to the cynicism and gridlock endemic to our politics today.

I’ve seen those changes from many vantage points—as a youthful campaigner in New York City in the tumultuous 1960s; as a Chicago newspaperman in the 1970s and ’80s, chronicling the waning days of America’s last great urban political machine and the emergence of a black independent political movement that laid the foundation for Barack Obama’s rise; as a political strategist for nearly three decades, working on campaigns rife with drama and change; and as a top aide to a trailblazing president facing epic challenges and impossible expectations. This book is the story of that journey, from my seat on the mailbox in more innocent times to the inner sanctums of historic campaigns and the White House.