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Chapter 1 focuses on Obama’s early life and formative years. The chapter opens with Obama’s recollections of living at the White House, notably, walking along the West Colonnade to get to and from the Oval Office. Obama describes his upbringing, stressing the positive influence of his maternal grandparents and mother, Ann Dunham. From the time Obama was young, Dunham stressed the importance of the civil rights movement, decried the Vietnam War, promoted the women’s rights movement, and supported the war on poverty. Barack Obama Sr., a Kenyan economist, was largely absent from his son’s life.
Obama describes his transformation from lackadaisical student to politically engaged Harvard law graduate. His awakening to his mixed-race identity, which coincided with his growing awareness of class distinctions, began in high school. His political awareness, however, did not begin until he attended Occidental College. Before then, he dismissed representative politics as rigged and focused on social movements led by ordinary people, like his mother. Obama became more serious about his studies after transferring to Columbia University, graduating with a degree in political science and international relations. He spent the following years as a community organizer in Chicago, where he observed the political maneuverings of Harold Washington, the city’s first Black mayor. In this period, Obama learned that political campaigns based on racial redress are bound to illicit fear and backlash. Moreover, he realized that a single, charismatic leader was not enough to bring about lasting societal change. Harold’s insistence on giving people hope, however, planted a seed in Obama’s mind. For the first time in his life, he began to consider a career in public office. He met with success at Harvard Law School, becoming the first Black head of the Harvard Law Review and graduating magna cum laude.
Chapter 2 opens with Obama’s relationship with Michelle. The couple met at a Chicago-based law firm where they both worked after Obama’s first year at Harvard. In Michelle, Obama found an intellectual peer with deeply held convictions. Following law school, Obama returned to Chicago to run one of the largest voter registration drives in Illinois history. He married Michelle in 1992, taught at the University of Chicago Law School, finished his first book, and joined a law office specializing in civil rights. Although Michelle supported him, she also warned that his chosen path was a hard one, though she too left corporate law to focus on a service-oriented career, directing a nonprofit youth leadership program.
The second part of the chapter focuses on Obama’s political career, which began in 1995. He participated in Alice Palmer’s congressional race while entertaining thoughts of filing her soon-to-be-vacant Senate seat. Obama ran a bare-bones campaign alongside two staffers, going door-to-door to gather signatures, all the while struggling with Dunham’s terminal cancer diagnosis. Problems arose when Palmer lost her congressional race and announced her intention to retain her Senate seat. Obama learned about irregularities with Palmer’s petitions, which contained invalid signatures. He mounted a challenge based on these irregularities and won her Senate seat. In the interim, however, his mother succumbed to her illness. For the next eight years, Obama commuted from Chicago to Springfield. As a junior senator from the minority party, however, he was largely kept in the dark. His joy at the birth of his daughter, Malia, tempered his professional frustrations, but also brought new tension as he struggled to balance work, marriage, and fatherhood. He pursued a congressional seat in 2000 and suffered a decisive loss.
Chapter 3 describes the years following Obama’s congressional loss. Obama and Michelle welcomed their second daughter, Natasha (Sasha), as he focused on teaching and the State Senate. Dreams of bridge-building politics and reaching wide audiences, however, prompted him to run for the United States Senate. Obama recruited skilled media consultant David Axelrod (Axe) and launched an audacious campaign with a skeletal staff. Several factors contributed to his win. First, his congressional loss taught him to communicate more effectively with the media using pithy soundbites. Second, he lined up endorsements from unions and popular members of the congressional delegation. Third, he shored up his resume by spearheading a series of important bills. Fourth, he raised his profile by giving a speech criticizing the US invasion of Iraq. Young members of Obama’s staff used the internet to spread his antiwar message. On weekends, Obama visited immigrant neighborhoods and Black churches across Chicago and beyond. Well-timed ads and endorsements from five large newspapers helped him win the Democratic primary. His victory made national headlines, as did his keynote speech at the 2004 Democratic National Convention. Obama beat his Republican rival by 40 points, the biggest margin for a Senate race in Illinois history.
In Washington, Obama focused on forging relationships with colleagues. As the minority party, the Democrats had little power, forcing Obama to push modest, nonpartisan measures. The prospect of influencing foreign policy, however, remained one of his priorities. Obama collaborated with the Chair of the Foreign Relations Committee and travelled to Ukraine to promote nuclear nonproliferation. He then flew to Houston to address people displaced by Hurricane Katrina, most of whom were Black. Their tales of hardship resonated with him, prompting him to embark on a media tour to discuss racism, intergenerational poverty, and the lack of opportunities in large parts of the country. He also drafted plans to rebuild the Gulf region. A visit to US troops the Middle East further fueled Obama’s desire to effect change in a global context.
Chapter 4 focuses on Obama’s decision to run for President. He first considered the possibility in 2006, after a conversation with Pete Rouse, his chief-of-staff. Despite Rouse’s encouragement, Obama remained reluctant because well-established Democrats had already laid the groundwork for presidential runs. Harry Reid (D–NV) encouraged Obama to take the idea seriously. Reid stressed Obama’s ability to mobilize and motivate people, especially youths and minorities. He also sensed that the American populace was ready for a different kind of president. Charles Schumer (D–NY) and Dick Durbin (D–IL) echoed Reid’s opinion, as did Ted Kennedy (D–MA).
Michelle opposed the idea of a presidential run. Shortly thereafter, the Obama’s traveled to Africa to visit Nelson Mandela’s prison cell in South Africa, meet with Bishop Desmond Tutu, and tour Obama Sr.’s ancestral home in Kenya. Obama continued the trip after Michelle and the girls returned to Chicago, going to the Kenya-Somalia border for a terrorism briefing, flying to Ethiopia to visit US troops, and traveling to Chad to meet with refugees from Darfur. Throughout the trip, people asked Obama if was running for president. A well-received speech in Iowa upon his return, and an interview on Meet the Press, fed the media frenzy.
The realization that he could win the Democratic nomination, and ultimately the presidency, made Obama anxious. Fueled by antipathy toward President George W. Bush, voters overwhelmingly supported Democrats in the 2006 midterm elections, giving them control of the House and Senate. Obama’s team began charting a path to the White House, despite Hillary Clinton’s emergence as a frontrunner for the Democratic nomination. Michelle’s support marked a turning point. She asked Obama what he could offer the American people that other candidates could not. Obama’s answer—to make Black people and other minorities feel like they belong, give them hope, and serve as a role model for children around the world—swayed Michelle to his corner.
Part 1, “The Bet,” focuses on Obama’s life before he became POTUS. He introduces several themes that recur throughout his memoir, notably, the importance of family. In Chapter 1, for example, Obama describes conversations with his mother, whose moral convictions had a profound impact on his world view. In addition to supporting the war on poverty and denouncing the Vietnam War as a misguided disaster, Dunham spoke to Obama about government corruption in Indonesia, where they lived for several years with Obama’s stepfather. At the age of 12, moreover, Dunham encouraged Obama to watch the Watergate hearings every evening to learn about the dangers of McCarthyism. Her efforts to instill in Obama a strong sense of right and wrong extended beyond the headlines. For instance, Dunham reprimanded Obama when he bullied a child at school, stressing that actions determined the kind of person one was:
You know Barry […] there are people in the world who think only about themselves. They don’t care what happens to other people so long as they get what they want. They put other people down to make themselves feel important […] Then there are people who do the opposite, who are able to imagine how others must feel, and make sure that they don’t do things that hurt people […] Which kind of person do you want to be? (6-7).
Dunham taught Obama to fight for racial justice. She spoke to him about the Civil Rights movement when he was a child. She also married two men of color: Obama’s father, who was Kenyan, and her second husband (the father of Obama’s half-sister, Maya), who was from Indonesia. Obama’s desire to be a role model for Black people and other racial minorities proved critical to his future, and to the country’s, as it convinced Michelle to support his dream of running for president. He recounts this critical conversation in Chapter 4: “‘I know that kids all around this country–Black kids, Hispanic kids, kids who don’t fit in–they’ll see themselves differently, too, their horizons lifted, their possibilities expanded. And that alone…that would be worth it.’ […] ‘Well, honey,’ [Michelle] said finally, ‘that was a pretty good answer’” (77).
Obama was right about the impact a Black president would have on American youths. He recalls a five-year-old Black boy touching his hair in the Oval Office, a moment captured in a picture titled Hair Like Mine by White House photographer, Pete Souza. An inner-city teacher also reported that her students started studying harder after Obama’s election.
Obama’s relationship with Michelle, Malia, and Sasha kept him grounded throughout his political career. Chapter 1 opens with Obama’s recollections of events that took place at the White House, many of them of national importance. Tellingly, he lends equal weight to simple family moments, such as Malia and Sasha racing to greet him with the dogs, Bo and Sunny, on surprise afternoon visits. In Michelle, Obama found a partner who supported his dreams even when she did not fully share them. Indeed, Michelle experienced many hardships because of Obama’s career, spending weekdays alone with the girls in Chicago during his time in the State Senate, campaigning with him even when she wasn’t entirely comfortable on stage, and working without rest for weeks at a time. Acutely aware of the sacrifices Michelle made, Obama experienced profound guilt before launching his presidential campaign: “For years now, I’d asked Michelle for fortitude and forbearance when it came to my political endeavors, and she’d given it—reluctantly but with love. And then each time I’d come back again, asking for more. Why would I put her through this?” (70).
Throughout his memoir, Obama strives to shed light on the American political process. In Chapter 2, for instance, he describes how partisanship is to blame for the disfunction of the State Senate of Illinois. He recalls opposing a tax break that favored industry in a period when the state was cutting services for the poor. He argued that the unjustified tax breaks violated the conservative market principles espoused by Republicans. Obama’s argument was logical, but it didn’t change any votes, not because his colleagues in the State Senate could not distinguish a good policy from a bad one, but because they prioritized party loyalty over good policy. Obama explains that going against party orthodoxy could cost politicians endorsements, financial backers, a leadership post, and even an election.
One of Obama’s greatest strengths inside and outside the political arena is his ability to focus on commonalities rather than differences. Throughout his career, he demonstrated his willingness to reach across the aisle. Obama’s emphasis on commonalities also helped him connect with voters. Chapter 3 describes his campaign for the US Senate, which had him interacting with various demographics. The more time he spent campaigning, the clearer it became that the people of his state wanted similar things–good jobs, affordable healthcare, affordable education for their children, safety from criminals and terrorists, and the ability to retire with dignity. Obama’s stump speech stressed these common desires, forging a connection with the audience that was palpable:
There’s a physical feeling, a current of emotion that passes back and forth between you and the crowd, as if your lives and theirs are suddenly spliced together […] You’ve tapped into some collective spirit, a thing we all know and wish for—a sense of connection that overrides our differences and replaces them with a giant swell of possibility (52).
Obama’s memoir is serious and methodical, but not without levity. In Chapter 1, he explains why his intellectual interests changed regularly during college. He read Karl Marx and Herbert Marcuse to impress “the long-legged socialist who lived in [his] dorm” (10). He studied the writings of Frantz Fanon and Gwendolyn Brooks “for the smooth-skinned sociology major who never gave [him] a second look” (10). Finally, he grappled with Michel Foucault and Virginia Woolf “for the ethereal bisexual who wore mostly black” (10). As Obama notes, this pseudo-intellectualism “proved mostly worthless” (10) as a strategy for picking up women. Obama’s ability not to take himself too seriously is also apparent in Chapter 3, which describes a weeklong RV trip to campaign in southern Illinois with Michelle and the girls. As the RV pulled up to their first destination, Malia asked what the crowed was doing there. Michelle explained that the people were there to see her father. Malia curtly replied, “Why?” Later in the chapter, Obama describes a trip to Lincoln Park Zoo with Malia and Sasha. Obama managed to go unnoticed until someone recognized him at the sea lion exhibit. The next thing he knew, he was surrounded by people wanting to shake his hand and take pictures with him. Afterwards, Malia suggested her father create an alias: “‘You need to disguise your voice,’ Malia added. ‘People recognize it. You have to talk with a higher voice. And faster’. ‘Daddy talks so slow,’ Sasha said” (60). Michelle joined in on the fun when Malia explained the plan later that day: “‘That’s a great idea, honey,’ she said, ‘but the only way for Daddy to disguise himself is if he has an operation to pin back his ears’” (60).
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