When Barack Obama worked as a community organizer amid the bleak industrial decay of Chicago’s far South Side during the 1980s, he tried to follow a mantra of that profession: Dream of the world as you wish it to be, but deal with the world as it is.

The notion of an Obama presidency was beyond imagining in the world as it was then. But, three decades later, it has happened, and a variation of that saying seems appropriate to the moment: Stop comparing Obama with the president you thought he might be, and deal with the one he has been.

Seven-plus years into his White House tenure, Obama is working through the final months before his presidency slips from present to past, from daily headlines to history books. That will happen at noontime on the 20th of January next year, but the talk of his legacy began much earlier and has intensified as he rounds the final corner of his improbable political career.



President Obama makes a campaign stop during a three-day bus tour in Boone, Iowa, in August 2012. (Nikki Kahn/The Washington Post)

Of the many ways of looking at Obama’s presidency, the first is to place it in the continuum of his life. The past is prologue for all presidents to one degree or another, even as the job tests them in ways that nothing before could. For Obama, the line connecting his life’s story with the reality of what he has been as the 44th president is consistently evident.

The first connection involves Obama’s particular form of ambition. His political design arrived relatively late. He was no grade school or high school or college leader. Unlike Bill Clinton, he did not have a mother telling everyone that her first-grader would grow up to be president. When Obama was a toddler in Honolulu, his white grandfather boasted that his grandson was a Hawaiian prince, but that was more to explain his skin color than to promote family aspirations.

But once ambition took hold of Obama, it was with an intense sense of mission, sometimes tempered by self-doubt but more often self-assured and sometimes bordering messianic. At the end of his sophomore year at Occidental College, he started to talk about wanting to change the world. At the end of his time as a community organizer in Chicago, he started to talk about how the only way to change the world was through electoral power. When he was defeated for the one and only time in his career in a race for Congress in 2000, he questioned whether he indeed had been chosen for greatness, as he had thought he was, but soon concluded that he needed another test and began preparing to run for the Senate seat from Illinois that he won in 2004.

That is the sensibility he took into the White House. It was not a careless slip when he said during the 2008 campaign that he wanted to emulate Ronald Reagan and change “the trajectory of America” in ways that recent presidents, including Clinton, had been unable to do. Obama did not just want to be president. His mission was to leave a legacy as a president of consequence, the liberal counter to Reagan. To gauge himself against the highest-ranked presidents, and to learn from their legacies, Obama held private White House sessions with an elite group of American historians.



Obama meets with former presidents Bill Clinton and George W. Bush in January 2010 to discuss the recovery and rebuilding efforts in Haiti after a devastating earthquake. (Marvin Joseph/The Washington Post)

It is now becoming increasingly possible to argue that he has neared his goal. His decisions were ineffective in stemming the human wave of disaster in Syria, and he has thus far failed to close the detention camp at Guantanamo Bay, Cuba, and to make anything more than marginal changes on two domestic issues of importance to him, immigration and gun control. But from the Affordable Care Act to the legalization of same-sex marriage and the nuclear deal with Iran, from the stimulus package that started the slow recovery from the 2008 recession to the Detroit auto industry bailout, from global warming and renewable energy initiatives to the veto of the Keystone pipeline, from the withdrawal of combat troops from Iraq and Afghanistan and the killing of Osama bin Laden to the opening of relations with Cuba, the liberal achievements have added up, however one judges the policies.

This was done at the same time that he faced criticism from various quarters for seeming aloof, if not arrogant, for not being more effective in his dealings with members of Congress of either party, for not being angry enough when some thought he should be, or for not being an alpha male leader.

A promise of unity

His accomplishments were bracketed by two acts of negation by opponents seeking to minimize his authority: first a vow by Republican leaders to do what it took to render him a one-term president; and then, with 11 months left in his second term, a pledge to deny him the appointment of a nominee for the crucial Supreme Court seat vacated by the death of Antonin Scalia, a conservative icon. Obama’s White House years also saw an effort to delegitimize him personally by shrouding his story in fallacious myth — questioning whether he was a foreigner in our midst, secretly born in Kenya, despite records to the contrary, and insinuating that he was a closet Muslim, again defying established fact. Add to that a raucous new techno-political world of unending instant judgments and a decades-long erosion of economic stability for the working class and middle class that was making an increasingly large segment of the population, of various ideologies, feel left behind, uncertain, angry and divided, and the totality was a national condition that was anything but conducive to the promise of unity that brought Obama into the White House.



Barack Obama Sr. poses with his son in this undated photograph. (Family photo via Bloomberg News)

To the extent that his campaign rhetoric raised expectations that he could bridge the nation’s growing political divide, Obama owns responsibility for the way his presidency was perceived. His political rise, starting in 2004, when his keynote convention speech propelled him into the national consciousness, was based on his singular ability to tie his personal story as the son of a father from Kenya and mother from small-town Kansas to some transcendent common national purpose. Unity out of diversity, the ideal of the American mosaic that was constantly being tested, generation after generation, part reality, part myth. Even though Obama romanticized his parents’ relationship, which was brief and dysfunctional, his story of commonality was more than a campaign construct; it was deeply rooted in his sense of self.

As a young man, Obama at times felt apart from his high school and college friends of various races and perspectives as he watched them settle into defined niches in culture, outlook and occupation. He told one friend that he felt “large dollops of envy for them” but believed that because of his own life’s story, his mixed-race heritage, his experiences in multicultural Hawaii and exotic Indonesia, his childhood without “a structure or tradition to support me,” he had no choice but to seek the largest possible embrace of the world. “The only way to assuage my feelings of isolation are to absorb all the traditions [and all the] classes, make them mine, me theirs,” he wrote. He carried that notion with him through his political career in Illinois and all the way to the White House, where it was challenged in ways he had never confronted before.


With most politicians, their strengths are their weaknesses, and their weaknesses are their strengths.

With Obama, one way that was apparent was in his coolness. At various times in his presidency, there were calls from all sides for him to be hotter. He was criticized by liberals for not expressing more anger at Republicans who were stifling his agenda, or at Wall Street financiers and mortgage lenders whose wheeler-dealing helped drag the country into recession. He was criticized by conservatives for not being more vociferous in denouncing Islamic terrorists, or belligerent in standing up to Russian President Vladimir Putin.



A young Obama with his mother, Ann Dunham, in the 1960s. (Family photo via Associated Press)

His coolness as president can best be understood by the sociological forces that shaped him before he reached the White House. There is a saying among native Hawaiians that goes: Cool head, main thing. This was the culture in which Obama reached adolescence on the island of Oahu, and before that during the four years he lived with his mother in Jakarta. Never show too much. Never rush into things. Maintain a personal reserve and live by your own sense of time. This sensibility was heightened when he developed an affection for jazz, the coolest mode of music, as part of his self-tutorial on black society that he undertook while living with white grandparents in a place where there were very few African Americans. As he entered the political world, the predominantly white society made it clear to him the dangers of coming across as an angry black man. As a community organizer, he refined the skill of leading without being overt about it, making the dispossessed citizens he was organizing feel their own sense of empowerment. As a constitutional law professor at the University of Chicago, he developed an affinity for rational thought.

Differing approaches

All of this created a president who was comfortable coolly working in his own way at his own speed, waiting for events to turn his way.

Was he too cool in his dealings with other politicians? One way to consider that question is by comparing him with Clinton. Both came out of geographic isolation, Hawaii and southwest Arkansas, far from the center of power, in states that had never before offered up presidents. Both came out of troubled families defined by fatherlessness and alcoholism. Both at various times felt a sense of abandonment. Obama had the additional quandary of trying to figure out his racial identity. And the two dealt with their largely similar situations in diametrically different ways.

Rather than deal with the problems and contradictions of his life head-on, Clinton became skilled at moving around and past them. He had an insatiable need to be around people for affirmation. As a teenager, he would ask a friend to come over to the house just to watch him do a crossword puzzle. His life became all about survival and reading the room. He kept shoeboxes full of file cards of the names and phone numbers of people who might help him someday. His nature was to always move forward. He would wake up each day and forgive himself and keep going. His motto became “What’s next?” He refined these skills to become a political force of nature, a master of transactional politics. This got him to the White House, and into trouble in the White House, and out of trouble again, in acycle of loss and recovery.

Obama spent much of his young adulthood, from when he left Hawaii for the mainland and college in 1979 to the time he left Chicago for Harvard Law School nearly a decade later, trying to figure himself out, examining the racial, cultural, personal, sociological and political contradictions that life threw at him. He internalized everything, first withdrawing from the world during a period in New York City and then slowly reentering it as he was finding his identity as a community organizer in Chicago.

Rather than plow forward relentlessly, like Clinton, Obama slowed down. He woke up each day and wrote in his journal, analyzing the world and his place in it. He emerged from that process with a sense of self that helped him rise in politics all the way to the White House, then led him into difficulties in the White House, or at least criticism for the way he operated. His sensibility was that if he could resolve the contradictions of his own life, why couldn’t the rest of the country resolve the larger contradictions of American life? Why couldn’t Congress? The answer from Republicans was that his actions were different from his words, and that while he talked the language of compromise, he did not often act on it. He had built an impressive organization to get elected, but it relied more on the idea of Obama than on a long history of personal contacts. He did not have a figurative equivalent of Clinton’s shoebox full of allies, and he did not share his Democratic predecessor’s profound need to be around people. He was not as interested in the personal side of politics that was so second nature to presidents such as Clinton and Lyndon Johnson.

Politicians of both parties complained that Obama seemed distant. He was not calling them often enough. When he could be schmoozing with members of Congress, cajoling them and making them feel important, he was often back in the residence having dinner with his wife, Michelle, and their two daughters, or out golfing with the same tight group of high school chums and White House subordinates.



Obama is sworn in as the 44th president by Chief Justice John G. Roberts Jr. on Jan. 20, 2009. (Jonathan Newton/The Washington Post)

Here again, some history provided context. Much of Obama’s early life had been a long search for home, which he finally found with Michelle and their girls, Malia and Sasha. There were times when Obama was an Illinois state senator and living for a few months at a time in a hotel room in Springfield, when Michelle made clear her unhappiness with his political obsession, and the sense of home that he had strived so hard to find was jeopardized. Once he reached the White House, with all the demands on his time, if there was a choice, he was more inclined to be with his family than hang out with politicians. A weakness in one sense, a strength in another, enriching the image of the first-ever black first family.

A complex question

The fact that Obama was the first black president, and that his family was the first African American first family, provides him with an uncontested hold on history. Not long into his presidency, even to mention that seemed beside the point, if not tedious, but it was a prejudice-shattering event when he was elected in 2008, and its magnitude is not likely to diminish. Even as some of the political rhetoric this year longs for a past America, the odds are greater that as the century progresses, no matter what happens in the 2016 election, Obama will be seen as the pioneer who broke an archaic and distant 220-year period of white male dominance.

But what kind of black president has he been?


His life illuminates the complexity of that question. His white mother, who conscientiously taught him black history at an early age but died nearly a decade before her son reached the White House, would have been proud that he broke the racial barrier. But she also inculcated him in the humanist idea of the universality of humankind, a philosophy that her life exemplified as she married a Kenyan and later an Indonesian and worked to help empower women in many of the poorest countries in the world. Obama eventually found his own comfort as a black man with a black family, but his public persona, and his political persona, was more like his mother’s.



An emotional Obama wraps up his final campaign with a stop in Des Moines on the eve of Election Day in 2012. (Nikki Kahn/The Washington Post)

At various times during his career, Obama faced criticism from some African Americans that, because Obama did not grow up in a minority community and received an Ivy League education, he was not “black enough.” That argument was one of the reasons he lost that 2000 congressional race to Bobby L. Rush, a former Black Panther, but fortunes shift and attitudes along with them; there was no more poignant and revealing scene at Obama’s final State of the Union address to Congress than Rep. Rush waiting anxiously at the edge of the aisle and reaching out in the hope of recognition from the passing president.

As president, Obama rarely broke character to show what was inside. He was reluctant to bring race into the political discussion, and never publicly stated what many of his supporters believed: that some of the antagonism toward his presidency was rooted in racism. He wished to be judged by the content of his presidency rather than the color of his skin. One exception came after February 2012, when Trayvon Martin, an unarmed black teenager, was shot and killed in Florida by a gun-toting neighborhood zealot. In July 2013, commenting on the verdict in the case, Obama talked about the common experience of African American men being followed when shopping in a department store, or being passed up by a taxi on the street, or a car door lock clicking as they walked by — all of which he said had happened to him. He said Trayvon Martin could have been his son, and then added, “another way of saying that is: Trayvon Martin could have been me 35 years ago.”

Nearly two years later, in June 2015, Obama hit what might be considered the most powerful emotional note of his presidency, a legacy moment, by finding a universal message in black spiritual expression. Time after time during his two terms, he had performed the difficult task of trying to console the country after another mass shooting, choking up with tears whenever he talked about little children being the victims, as they had been in 2012 at Sandy Hook Elementary School in Newtown, Conn. Now he was delivering the heart-rending message one more time, nearing the end of a eulogy in Charleston, S.C., for the Rev. Clementa Pinckney, one of nine African Americans killed by a young white gunman during a prayer service at Emanuel African Methodist Episcopal Church. It is unlikely that any other president could have done what Barack Obama did that day, when all the separate parts of his life story came together with a national longing for reconciliation as he started to sing, “Amazing grace, how sweet the sound, that saved a wretch like me. . . .”