A Promised Land

it’s the year 2000. in los angeles, the democratic national convention is about to start, and barack obama is having a week. for one thing, he’s just experienced the worst loss of his short political life, a 30-point thumping by an incumbent in the us house of representatives. making matters worse, when he lands in la, his maxed-out american express card is declined by the rental car agency. and when he finally arrives at the convention, his credentials are deemed suspicious, so he can’t even get onto the convention floor. the cherry on top comes when he’s denied entry to the chichi after-party. at this, obama gives up and goes back to the airport. 

that could have been the end of the story for obama. at the time, he was but a lowly state senator from illinois. but he had more than credit card debt and sub-optimal clout for la party attendance: he had a dream to unite americans of different political persuasions and from different racial and socioeconomic backgrounds. he came close to giving up in 2000. but he didn’t. and four years later, at the next dnc, he gave the keynote address. four years after that, he became the first black man to accept the democratic nomination for president.

you may think the rest is history. but obama’s true journey – a journey from an unremarkable childhood in honolulu, hawaii, punctuated by drug use and mediocre grades, to sitting as the first black president in the situation room, ordering the raid that led to the death of osama bin laden – is more fraught with self-doubt, compromise, and turmoil than most people might imagine. these chapters take an unprecedented peek into obama’s innermost thoughts throughout his life, from earliest childhood to 2011.

in these chapters, you’ll learn

• exactly what kind of ladies obama was trying to attract by flexing his knowledge of foucault and marx;
• how many cigarettes obama smoked per day in the white house – and what made him finally quit; and
• the catty remark mitch mcconnell made to joe biden on the senate floor – that biden never forgot.

barack hussein obama was a nice enough kid. born in 1961, he grew up with his mother and grandparents in honolulu, hawaii. but neither his mother nor his grandparents would ever guess he’d end up in public office – let alone become president. he was a mediocre student and an adequate basketball player. the only thing he really paid close attention to was partying. 

but at some point in high school he started asking questions his grandparents couldn’t answer, like why were most professional basketball players black, but none of the coaches? why did people his mother considered good and decent struggle so much financially? to answer these questions, he turned to books.

it was this voracious reading habit that gave him a halfway decent sense of politics when he landed at occidental college, in los angeles, in 1979. in college, he kept up with his reading, but mostly to impress girls. he read foucault to engage with the elegant bisexual who wore all black. he studied marx to impress the lithe socialist from his dorm. it didn’t get him very far with the ladies, but it did teach him a few things about political theory.

when he transferred to columbia, he became obsessed with the idea of politics in practice. all this political carrying on meant he wasn’t much fun to hang out with – and the few friends he had didn’t hesitate to tell him so. but he was fine being alone with his ideas. he just needed somewhere to go to put them into practice. 

upon graduation, he took a job in chicago, working with a group trying to stabilize communities adversely affected by steel plant closures. this work finally got his head out of the theory books. it forced him to listen to real people, to hear their real problems. it also helped him understand his identity as a mixed-race black man.

still, he wasn’t satisfied with the effect he was having. change was coming too slowly. he wanted more power, power to shape budgets and to guide policy that could have a real impact on these communities. he decided to apply to harvard law school – and he was accepted. the next fall, he moved to boston to begin the next stage of his journey.

but, as it turns out, obama’s law-school experience was a lot like his undergraduate experience. he spent all his time reading about civics. but this time, he was better rewarded for it: he was elected head of the harvard law review; he got his first book deal; and high-paying, high-status job offers came pouring in. 

these offers were gratifying, but obama ended up taking a different route.

obama’s first true watershed moment was in 2000. his life seemed to be going ok: he’d married michelle, a whip-smart and gorgeous lawyer from chicago, and they’d had a beautiful daughter, malia. he’d taken two jobs in chicago, practicing and teaching law. he also had an early opportunity to run for state senate – a race he won, twice. 

but it wasn’t enough for him. despite michelle’s protestations that she needed him around more, he decided to run for the house of representatives against a popular incumbent. it was a bold move, and it didn’t quite go as planned. he lost by 30 points.

looking hard at his choices, he realized that he didn’t like the way his life was turning out. after all, he’d made an arrogant decision to run a race he couldn’t win. worse, he was letting down his young family.

nonetheless, he couldn’t bring himself to fully turn away from politics. he still believed in his dream of uniting americans of different political persuasions, from a range of racial and socioeconomic backgrounds. the trouble was, this type of politics just wasn’t suited to local races. what he needed to do was run for national office – like the senate. so he resolved to try one more time. if he failed again, he’d give up politics without regret. michelle gave her reluctant blessing.

this time, he found a secret weapon: david axelrod, a journalist turned political-media consultant. axe knew that obama had a persuasive message – he just needed to deliver it more effectively. axe’s influence soon paid off: before obama had even announced his candidacy, a speech he gave expressing disapproval of the iraq war went viral on blogs and myspace. not that he knew what any of that meant; he needed the help of his young campaign staff to understand the online world. 

momentum grew. small donations and volunteers came pouring in. obama and his staff realized that they’d tapped into something: his speeches spoke to people’s real problems, and his candidacy reflected a hope that some americans thought had all but vanished. 

before the election, the opportunity of a lifetime came up. he was invited to give the keynote address at the 2004 democratic national convention. sprawled on his hotel room bed in springfield, illinois, he wrote the speech on yellow legal pads. he tried to sum up the politics he’d been searching for since college, informed by lessons he’d learned from his parents and grandparents. he settled on a phrase he remembered from his pastor back in chicago: the audacity of hope. 

it was a seminal moment in his career, the last time he could walk into a room unrecognized. a few weeks later, he was elected to the senate, winning by a landslide.

after his dnc speech, the hype surrounding obama quickly became ridiculous. it was already becoming difficult for him to do normal things. one day after a chaotic visit to the lincoln park zoo, his daughter malia suggested he adopt the alias johnny mcjohn john to be more anonymous. michelle retorted that he could only be really anonymous if he had an operation to pin his ears back. 

pretty much as soon as he stepped off the dnc stage in 2004, people started telling him he’d one day be president. his own convictions weren’t that strong. but somehow, by the spring of 2006, running for president no longer felt like an impossibility. the media wouldn’t take no for an answer, no matter how many times he denied it. when nevada senator harry reid said he should think about it, his hard-line stance softened. but it was a visit with senator ted kennedy that finally changed his mind. invoking his idealistic brothers, john and robert, kennedy looked into obama’s eyes and told him, “moments like this are rare. you think you may not be ready. but you don’t choose the time. the time chooses you.”

obama announced that he would run for president in february 2007, then went straight to iowa to start stumping for that state’s critical primary caucus. people turned out to see him in their thousands. “this is not normal,” said one veteran iowa political operative. 

but obama wasn’t a sure thing. he was a young and inexperienced candidate. worst of all, he was a professor – and it showed. instead of giving pithy soundbites, he actually tried to answer interviewers’ questions. the other, more experienced candidates took a different approach, using interviews as a platform to deliver their message. 

the campaign had two things going for it: first, a top-notch team led by david axelrod. the second thing was money. as the campaign grew, the makeup of their donor base shifted, from large benefactors to small, grassroots donors. they also had an army of enthusiastic young volunteers, who turned out in droves to help in iowa.

obama’s momentum had the other candidates quaking in their boots, especially hillary clinton, who many presumed would be the democratic nominee. the animosity between the two campaigns culminated in a yelling match between obama and clinton on the tarmac between their two planes in des moines, iowa. 

but the clinton campaign's underhanded tactics and the shouting match had little impact. obama won iowa decisively, by eight points. the race was on.

the iowa high wouldn’t last: they lost new hampshire, the very next primary race. but obama now sees this loss as one of the most important moments in the campaign. they now understood that it wouldn’t be as easy as it had seemed. the staff gritted their teeth and got back to work. 

there were more problems in store. an old friend of obama’s, the reverend jeremiah wright, was caught on tape giving wild opinions about white supremacy and “black inferiority” at a sunday church service. it brought up some old issues for obama around his complex relationship with the black community. some among them thought america wasn’t ready for a black president; others thought he wasn’t “black enough” to represent the community. 

it wasn’t just some in the black community who had problems with obama. the right-wing press was parroting some silly rumors, accusing him of having been a drug dealer and a gay prostitute. there were also more insidious, race-based attacks leveled against both him and michelle. one fox news segment described michelle as “obama’s baby mama.”

but nevertheless obama kept winning. in south carolina, he was buoyed by a historic black turnout. people of all backgrounds went wild at obama’s rallies. after his stump speeches, admirers would scream and cry, touch his face, and demand he hold their babies. the rallies gave obama and his team energy. but obama also worried that he was becoming a locus for a million different hopes and dreams. he would inevitably be a disappointment. 

and then reverend wright was back in the news. a compilation video was circulating, highlighting all the inflammatory things he’d said throughout the years, including “god damn america.” it was like catnip to talk-radio-loving red-state voters who were uncomfortable with the thought of a black man in the white house. even the most optimistic members of the campaign admitted they might not survive this. 

obama decided to go for broke. he spent the next few days working on a speech on race. he wanted to communicate to americans that while reverend wright was indeed a part of his narrative, he wasn’t the whole story. obama’s white grandmother, a woman who sometimes got scared when passing black people on the street, was part of that story, too. regardless of whether the speech landed, obama figured he’d be saying what he meant. 

he needn’t have worried. the speech landed. one million people watched it within 24 hours – a record at the time. 

they had successfully staunched the bleeding. with the next round of primary wins, it was clear that obama would be the nominee.

when it came time for obama to pick a running mate, joe biden wasn’t the immediate choice. on paper, the two men were polar opposites. biden, nineteen years older than obama, was a career congressman. obama was a young upstart. biden’s warmth and lightheartedness were a far cry from obama’s professorial cool. but he was smart, compassionate, and paid attention – and, above all else, he had heart. it was an easy decision in the end. 

obama was enjoying a clear advantage in the polls when john mccain, the republican nominee, announced his own running mate – a press release that prompted joe biden to ask, “who the hell is sarah palin?” joe, and the country, soon found out. 

she was the governor of alaska, an arch-conservative small-town girl with an aw-shucks working-class energy. she didn’t know what she was talking about on a variety of issues, but that didn’t matter to voters, who were thrilled to see someone like them up on stage. it was evidence of a larger, darker reality in which partisan allegiance and political machinations threatened to blot out everything else. 

john mccain was a good man – obama had seen him display real courage in the senate. but the republican nominee was being pulled to the right by his party and the increasingly populist sentiment in the electorate. 

yet mccain and palin weren’t the worst of obama’s problems. the global financial system was about to take a catastrophic tumble, and it was not at all clear when – or whether – it would recover.

when the nation’s largest lenders of subprime mortgages started declaring bankruptcy in late 2007, things started unraveling fast. financial institutions announced billions in losses, the markets reacted badly, and by spring 2008 the us had entered a recession. 

mccain’s campaign struggled from early on. and when mccain made the desperate, hail-mary move of suspending his campaign to purportedly deal with the financial crisis, it became clear to nearly everyone that obama was going to win. shepherd fairey’s hope poster depicting obama’s face in red, white, and blue started showing up everywhere. “you’re the new in thing,” obama’s longtime friend and advisor valerie jarrett told him.

on election day, obama played basketball, then rode the deserted chicago streets to the downtown hotel where he and his family would be watching the returns. as the results started coming in, obama sat down next to his mother-in-law, marian robinson, who had grown up in a time when the thought of a black president seemed as likely as a flying pig. “this is kind of too much,” she said, watching the states turn blue.

a president’s schedule is packed, from the moment he or she is elected. but, during the winter of 2008, there was only one thing that truly mattered: halting the economy’s collapse. the stock market had lost 40 percent of its value. there were foreclosure filings on 2.3 million homes. household wealth had dropped more than five times what it had during the great depression. things were so bad that obama took up smoking again, up to ten cigarettes per day.

the first thing to do was pass a fiscal stimulus bill, pumping money into the economy until it could get going again. the proposed bill offered a range of benefits: more food stamps, extended unemployment insurance, middle-class tax cuts, and aid to states to help them avoid laying off teachers, firefighters, and other employees. but getting it through congress was far from a sure thing. 

the truth was that congress didn’t work very well. bipartisanship was a nostalgic thing of the past. even at this point, most center-of-the-road politicians were barely clinging to their seats. a new breed of politician, disciples of newt gingrich, rush limbaugh, and sarah palin, had come to power. these people didn’t compromise. 

they were led by mitch mcconnell, the republican senate leader. mcconnell was bland and uncharismatic, more interested in unwavering partisanship than in the details of policy. he was also pretty rude: joe biden told obama about a run-in they’d had on the senate floor, when biden approached mcconnell to discuss a piece of legislation. mcconnell raised his hand to stop him, as though he were directing traffic. “you must be under the mistaken impression that i care,” he’d said.

obama was committed to working across the aisle. but as each day passed, republican cooperation dried up even further. word got back to him that mitch mcconnell had been pressuring his caucus to not even speak to white house staff about the stimulus bill, trying to prevent obama from accomplishing anything – regardless of the consequences for the country.

ultimately, the recovery act got zero republican votes. there were enough democrats in the house to pass it anyway, but the total republican shut-out was the opening shot in a war that mcconnell and his cronies would wage on obama for the next eight years. 

this republican resistance, which hardened in the first few weeks of obama’s presidency, colored how the press and the public viewed it. it also set the course for a cleaving of america’s political sensibilities that caused massive, unprecedented fallout, which we’re still dealing with today. 

one day, about 100 days into his presidency, obama had a meeting with tim geithner, the secretary of the treasury. normally, obama could tell how bad the numbers were just by the expression on geithner’s face. but this time was different: the economy looked like it was turning a corner.

but by now, the financial crisis had reached every corner of the globe, and was the dominant issue on the table at the 2009 g20 summit in london. obama’s job was to convince the entire g20 that fiscal stimulus was the right move, including recalcitrant countries like russia and china. of the european contingent, angela merkel and nicolas sarkozy were new acquaintances. merkel was a patient, methodical leader with bright blue eyes that sometimes betrayed deep emotion. she and obama hit it off right away. sarkozy, on the other hand, was all emotional outbursts. he also wore lifts in his shoes, obama noted with amusement. 

after wheedling that would become typical at these summits, the g20 struck a stimulus deal. sarkozy was so excited that he started chanting geithner’s name, to the chagrin of the taciturn merkel. 

back at home, ted kennedy had given the obamas a present: a portuguese water dog. they named this fluffy pink-tongued black-and-white bundle of joy bo. he quickly became a cherished member of the obama family. 

but teddy kennedy was terminally ill with a brain tumor. at this late stage, there was one issue that could have forced him from his bed: health care. for decades, the american health-care system had been broken. in 2009, more than 43 million americans were uninsured, and premiums for family coverage had risen 97 percent since 2000. costs for health care were spiraling out of control. 

obama’s team was worried about what would happen if he took a big swing – attempting to introduce universal health care – and missed. with congress in disarray, pushing through health-care legislation was far from a sure thing. but, because of the recession, his poll numbers were going to take a hit anyway. for obama, to let fear get in the way of helping millions of people get health care would have been unconscionable. kennedy joined obama for a press conference on the issue, one of his last public appearances.

the politics of such a law would be mind-numbingly complicated, so obama insisted on shaping the bill in such a way that it could garner at least some republican support. but republicans had other plans.

republicans were against the affordable care act from the very start. after market-testing around 40 anti-reform messages, they realized that describing the plan as a “government takeover” made republican voters the most angry. mcconnell launched offensives against the legislation using exactly this language. 

their efforts to rile up the public were working. in the summer of 2009, the so-called tea party was in ascendance. the tea party was an effort by the right wing to attract voters by magnifying their fears. local tea party chapters mobilized their supporters against what they dubbed “obamacare” using the same social-media tools that obama rode to the presidency. one of their favorite talking points was an old rumor that obama had actually been born in kenya, and was thus ineligible to be president. 

obama didn’t think he could counter this wave of opposition. but he did think he could help congressional democrats feel a little stronger. so his team organized a prime-time address before a joint session of congress. the speech was marred by an unprecedented show of disrespect by a congressman from south carolina, who shouted “you lie!” at obama in the middle of his speech.

but obama still managed to push the affordable care act through the senate, on christmas eve 2009, after 24 straight hours of debate. a few months later, after a wrenching battle, it also passed in the house. obama and his team were jubilant. it was a promise fulfilled. 

it also seemed like a pretty good time to quit smoking. obama hasn’t touched a cigarette since.

from the moment obama was inaugurated, his team had known that the midterm elections would be tough. they had tried to do a lot in two years, taking full advantage of the democratic party’s control of congress and its supermajority in the senate. they had accomplished a lot: they’d saved the economy from a depression and stabilized the global financial system. and they’d passed a historic health-care bill. that alone was more than any congress had accomplished in the past 40 years. but the economy was still in the gutter. people didn’t care that things could have been even worse had obama not stepped in. they were still suffering. 

that year, the democrats lost 63 seats in the house, the worst beating a party had taken since the 1930s. they also lost their senate supermajority, which meant things were about to get a lot harder.

obama’s first years in office taught him that he was at heart a reformist, not a radical. some of his foreign policy decisions reinforced that perspective – but others forced him to revisit his values, and the extent to which he could live up to them. 

the war in afghanistan is an example where a radical approach would have been catastrophic. the situation on the ground – a corrupt, ineffectual government and a population that largely lived according to the whims of the taliban – meant that a total troop pullout was never an option. in fact, the joint chiefs of staff were recommending a huge new deployment – seventeen thousand more troops against a taliban summer offensive. 

then, almost as soon as obama had authorized the additional troops, the joint chiefs and the commander of us forces in afghanistan asked for another forty thousand troops. so much for being an anti-war president. but the alternatives were worse. 

meanwhile, he got a call from the nobel committee: they were awarding him the nobel peace prize. he was shocked. “for what?” he asked his aide when receiving the news. he wasn’t promoting peace – he was sending more young people to war! it seemed to be indicative of a widening gap between the reality of obama’s presidency and the expectations that others had of it. 

soon enough, there was another development overseas that forced obama to confront the chasm between his values and the reality of his capabilities. 

in 2010, egypt erupted in protests. thousands of demonstrators poured into tahrir square, calling for the removal of the out-of-touch, elderly autocrat hosni mubarak. 

had obama been a candidate or a senator, the decision to support democratic reform would have been easy. but president obama was forced to contend with the fact that the us had a vested interest in a stable egypt – that meant an egypt where mubarak carried on as dictator, even at the expense of democratic processes. worse, the muslim brotherhood, an islamist organization, was the country’s most powerful political group. if the group took power, it could spell trouble for relations between the us and the middle east.

ultimately, obama decided to go with his conscience: he spoke in support of the protestors and asked mubarak to resign – first on a private phone call, and then publicly. when mubarak stepped down, it was the true end of an era in the middle east. but it set off events that would spell catastrophe all over the region – for thousands of protestors in syria and bahrain, and for a group of americans in benghazi, libya, a few years later.

osama bin laden, the architect of the 9/11 attacks, had been unaccounted for since december 2001. shortly after he assumed office, obama told his staff that he wanted to make the hunt for bin laden a top priority. bin laden’s continued freedom was a taunt to american power, he figured, and a painful issue for the 9/11 families. 

in 2010, his request finally bore fruit. cia analysts had found a compound in abbottabad, pakistan, where they had gathered intelligence on a man they called the pacer. the pacer, who was well over six feet tall, never left the compound, and he burned his trash instead of throwing it out. he had the same number of wives and children as osama bin laden. for exercise, he walked in circles in the compound’s garden. the cia put the probability of it being bin laden between 60 and 80 percent.

it was now up to obama to decide how, and whether, he would authorize a raid – without the knowledge of the pakistanis, or anyone else beyond those who absolutely had to know. the slightest information leak would mean mission failure, as bin laden would certainly disappear without a trace as soon as he caught wind that the americans were onto him. 

after holding onto the secret for nearly two years, obama decided to authorize a special ops mission. a navy seal team would fly into pakistan from afghanistan by helicopter to raid the compound, kill bin laden, and escape before the pakistani police or military knew they were there. 

as the days ticked by, tension mounted to a fever pitch. the day of the raid, obama could hardly work. he nervously played cards with his staff as he waited for nightfall in pakistan. when it came, he and his team crowded into a tiny room surrounding an army technician. it was the first and only time he would watch a live military action, and the 20 minutes it lasted were excruciating. but then they got the word they’d been waiting for: bin laden had been killed in the house. 

as word got out, crowds gathered outside the white house to celebrate, chanting usa! usa! it represented a small shift in the country’s mood – for a little while at least. similar to obama’s election three years prior, people took satisfaction in seeing their country deliver a historic victory. it was the first time in his presidency that obama didn’t have to sell what he’d done. 

on his way back to the white house from congratulating the successful seal team, obama felt himself relaxing as he looked down over the shimmering potomac river, winding its way through dc. he had accomplished something important, something historic. there was a long road ahead – more battles with mcconnell’s recalcitrant congress, a tough reelection fight, and untold fraught decisions and hard truths to face. but for this night, at least, he could breathe a sigh of relief. 

obama’s presidency was far from predestined. along the path he took from teenaged honolulu chiller to the first black american president, there were missteps, disappointments, and downright stupid decisions. he battled arrogance, entitlement, and preconceived notions – battles he still fights to this day. but obama overcame the obstacles in his personal life the way he hopes america can move forward as a nation: by learning to reconcile the duelling aspects of his own nature. by marrying his black and white backgrounds, as well as the working class values of his upbringing with his own ivy league idealism, obama learned how and when a person – and a president – should compromise. and, perhaps more importantly, when they should stand strong for what they believe.