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Obama's legacy, and future, is rooted in Chicago’s South Side

America's 44th president

Decoding Obama's West Wing, from Chicago's South Side

As Barack Obama prepares to leave office, Adam Radwanski asks the community organizers he worked with 30 years ago to square his performance in the White House with the eager young idealist who once pounded the pavement at their sides

After working and organizing on the streets of Chicago, where he also endeavoured to build relationships with local politicians, Mr. Obama enrolled at Harvard University in the fall of 1988.

The first time he laid eyes on Barack Obama, Alvin Love thought he was an addict coming to ask for a handout.

As a young pastor in a rough corner of Chicago's South Side, back in 1985, Rev. Love had already grown accustomed to a steady parade of such visitors. "So when I saw this guy come by with his sleeves rolled up, all gangly," he recalled recently, pointing out the same window of the Lilydale Baptist Church where he saw Mr. Obama approaching, "I thought, 'Oh no, here comes another one.'"

Only, once he opened his door, and his guest started talking – delivering a spiel about his funny name and non-local accent – did Rev. Love realize he was looking at his neighbourhood's new community organizer.

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From that point on, as they became friends working together in common cause, Rev. Love formed more accurate impressions of the man who would serve as his country's 44th president – as did others who worked alongside Mr. Obama back then.

This past fall, as Americans prepared to vote for President Obama's successor, I tracked down some of the people who knew him in his formative years in Chicago, to ask what they made of his presidency and how it squared with their observations of him after he had arrived in their city fresh from a graduate degree at Columbia.

What emerged was a picture of Barack Obama that serves as a useful lens for making sense of his time in office – its successes, its shortcomings, and perhaps even the peculiar way it is ending, with an ostensibly popular president about to be replaced by his polar opposite.

No, Mr. Obama is not exactly the same man he was back then. In the near quarter-century between his appearance on that church's doorstep and his move into the White House, he broadened his intellectual horizons with a law degree at Harvard; learned the political ropes during six years in Illinois's state senate and a brief stint in the U.S. one; became a family man.

In the speech that brought him into the national spotlight, at the 2004 Democratic National Convention, Mr. Obama famously pronounced, “There is not a liberal America and a conservative America; there is the United States of America!”

But in those early years on the South Side, Mr. Obama both developed and displayed a view of public life that helps explain why his presidency has been so different – more rational and pragmatic, less ideological and romantic – than many people had expected at its outset.

In 2008, when voters were projecting whatever they wanted onto a candidate with little national track record, Mr. Obama's background in community organizing was used to fill in ideological blanks. To supporters on the left, his fight for social causes in impoverished, overwhelmingly African-American neighbourhoods fit into a narrative of civil-rights activism and spoke to a deep passion about issues they cared about. To a suspicious right, modern community organizing's roots with the rabble-rousing Saul Alinsky – author of Rules for Radicals, which promised to teach "Have-nots" how to seize power from those who hold it – proved that Mr. Obama was a dangerous socialist.

If he had actually wanted to be an ideological warrior, the circumstances over the past eight years – a Great Recession fuelling public anger at financial elites; mounting political polarization coupled with shifting demographics that favour his Democrats – could hardly have been more ideal. From a certain perspective, maybe an ideological warrior is what his country needed. Had he run a little more hot – channelled Americans' anger rather than seeking to calm them – perhaps Donald Trump would not be about to assume the presidency.

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But that was never who Mr. Obama was.

"He wasn't ideological," said Jerry Kellman, the veteran activist who recruited Mr. Obama to Chicago in order to run the Developing Communities Project, and who mentored him, "and he still isn't."

As an organizer, Mr. Obama did not push big, predetermined ideas. His job was to help achieve incremental change by learning about local residents' practical needs – job training, say, or environmental cleanup around a specific housing development – and help them make their case to people in positions of power.

While often describing him as "progressive," those who worked alongside Mr. Obama say that he wasn't overly emotional, anti-establishment, or inclined toward confrontation – putting him at odds with those more dogmatic about Alinskyism, which is very much about making life uncomfortable for elites.

What he was: a cool-headed realist, mindful that the perfect can be the enemy of the good and that trying to fix all the world's problems is a fool's errand; but optimistic about his ability to bring all sides together to behave like rational adults and achieve mutually beneficial consensus, even if that consensus fell short of their respective ideals.

He wasn’t ideological, and he still isn’t.

Jerry Kellman, the veteran activist who recruited Mr. Obama to run the Developing Communities Project

Generally patient, he could also display something else that would echo later: annoyance with those who, in his view, didn't see things as rationally as he did. Johnnie Owens, whom Mr. Obama trained as his replacement after the two became friends working alongside each other, recalled Mr. Obama's expressing dislike for more grievance-based African-American leaders such as Jesse Jackson, a Chicago icon. And even as he tried to build relationships with local politicians, he was privately disdainful of their transactional self-interest.

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Maybe Mr. Obama decided during his time as an organizer, which inevitably involved a few victories and many frustrations, that if he couldn't beat those politicians, he would join them. Or maybe, as Mr. Owens and others suspect, he was eyeing an entry into politics all along.

Either way, there was no mystery within his circle about his long-term plans when, after three years of organizing, he decamped for Harvard; his message, upon announcing his departure, was that he would be able to do more good on the other side of the table, with the politicians. But neither was he animated by a particular policy mission; he seems to have believed he would bend the universe's moral arc toward justice – as he would later quote Martin Luther King Jr. – by tackling issues as they arose.

Barack Obama when he was a community organizer in Chicago. Loretta Augustine-Herron said it was notable he was captured eating something, as he ate sparingly in those days.

As his time in the White House reaches its end, it's obvious that in many ways, Mr. Obama exceeded the grandest expectations, from back then, of how he might employ his problem-solving skills. As President, he inherited an economy on the brink of collapse, and calmly navigated it to solid ground. He improved his country's image around much of the globe, lifting it from an all-time low. Convinced that health-care reform was the single biggest way to shrink inequality, he achieved reforms that dramatically reduced the number of uninsured Americans. He launched the first serious U.S. effort to tackle climate change. He did all that, and much else, while maintaining an even keel and an integrity that is already prompting nostalgia (and the highest approval ratings since his earliest days in office).

At the same time, it is impossible to ignore what the election of Mr. Trump says about his record, or at least what a large segment of his country thinks about it. The economic recovery has not been balanced; millions of Americans feel cast aside. The neighbourhoods where Mr. Obama once organized are going through some of their toughest – and most violent – times in decades. The world hardly seems a safer place than it was eight years ago, recent horrors in Syria serving as a stark reminder of how his caution and reserve sometimes come off as indifference. And for all his potential to bring people together, the 2016 election showcased a country as divided as ever – along partisan, racial and socioeconomic lines – and deeply pessimistic about its general direction.

Obama blames political divisions for the traction of fake news

Maybe none of this – the legacy of a conspicuously rational president in times that seem to border on the irrational – should be surprising. Especially not when you consider that the signs were all there for how Mr. Obama would address the biggest challenges of his era.

As the economy teetered, a cool aversion to class warfare

"He was so even-tempered," said Loretta Augustine-Herron, a teacher whom Mr. Obama trained as a volunteer back in his organizing days, and who in turn became something of a mother figure to him at the time. "I would be like 'Zing! Boom!' and he would take that second breath and start over."

Sitting in her living room in Calumet City, a predominantly African-American suburb not far from the South Side area where she then lived and pounded the pavement, she spoke with admiration of how Mr. Obama kept his emotions in check, no matter how unfair the world seemed. Others, like Jerry Kellman and Johnnie Owens, suggested that that calm went hand-in-hand with an aversion to class warfare, even when established power structures offered the most cause for frustration.

To hear their accounts was to better understand the economic-recovery strategy that, more than anything else, would define Mr. Obama's presidency – a response to the spectacular and infuriating mess he inherited in 2009, when a lot of Americans wanted blood.

Loretta Augustine-Herron poses for a portrait at her home in Calumet City, Illinois January 5, 2017. Ms. Augustine-Herron worked with Barack Obama on the south side of Chicago prior to him becoming president, when he was an organizer for Developing Communities Project.

If he had more populism in him, that metaphorical blood might have flowed: The worst financial meltdown since the Great Depression came with easily identifiable villains – bankers from whom he could have claimed many pounds of flesh for the subprime crisis.

If he were more ideological, he would have done everything he could to score victories for the left – dramatically curtailing capitalism's excesses, or massively expanding government – at a time when such victories might have felt earned.

Instead, he did what he had always done – living up to Mr. Owens's description of him as someone who, more than anyone else he had ever encountered, was adept at maintaining a public face. Privately, by Mr. Obama's own subsequent account, he was appalled and infuriated by daily briefings that showed the consequences of Wall Street's excesses. But he wasn't about to let such feelings get in the way of how he conducted himself as President.

Showing a long-standing preference for trying to get the best out of people on the inside, rather than aggressively challenging them as a relative outsider, he surrounded himself with officials who arguably bore some responsibility for the economic mess – most notably Tim Geithner, the Wall Street-friendly former regulator he chose as treasury secretary; and Larry Summers, named director of Mr. Obama's National Economic Council, even though he had had a strong hand in Bill Clinton's financial deregulation.

Among the swiftest decisions Mr. Obama made, despite knowing it would cause white-hot anger among people who felt they were being left to fend for themselves as they lost homes or savings, was to bail out banks. It was something he "hated" doing, he later conceded, but believed was more responsible than letting those banks collapse under the weight of their own mistakes. While shepherding in new rules that curbed risk-taking and that improved consumer protection, he declined to make the banks pay with the scale of regulatory reform for which there was widespread demand.

I looked at him through that first term, and the fact that he didn’t ram things through was typical Barack.

Loretta Augustine-Herron, who volunteered for Mr. Obama at the Developing Communities Project

To Mr. Kellman, it was consistent with an imperative that Mr. Obama had learned and embraced when he trained as an organizer: When "working with folks who have the decks stacked against them" – in this case, arguably, much of the population that had just elected him – the objective is to "accomplish something specific that has an immediate impact," even if it requires compromise. Economic stability trumped deeper Wall Street reform, as a matter of short-term practicality.

Partly in hope of appeasing Republicans (and conservative Democrats, who held the balance of power in Congress), and because he was trying to reserve political capital for health-care reform, he settled for a stimulus package of about $800-billion – less than half what his more-left-of-centre advisers advocated. And toward the end of his first term, as many in his party clamoured for another round of stimulus to speed up the recovery, he embraced deficit reduction, in another attempt at consensus with Republicans, who by then controlled the House.

Even though he appeared then to succeed in pleasing almost no one, Mr. Obama's economic strategy – which also included such then-controversial moves as bailing out auto companies – looks much better in retrospect. The recovery was slow, but much stronger than what's been managed by other nations (including much of Europe) that suffered similar consequences from the financial crisis. Mr. Obama can boast of presiding over the longest-ever U.S. streak of consecutive months with job growth. Census data suggests acceleration in the growth of household income toward the end of his tenure. The deficit, meanwhile, went from nearly half the federal budget in 2009 to 12.5 per cent of it. Consumer confidence, as he leaves office, is soaring.

There is data, too, to back up his pursuit of Obamacare at the expense of other potential initiatives (notwithstanding the fact that Republicans are already working to repeal it). Despite continuing middle-class anger about rising premiums, the Affordable Care Act made for about 20 million fewer uninsured Americans – which, among other benefits, dramatically reduced their risk of personal financial crisis.

But among the dangers for any president living that job's isolated existence, and especially an individual who embarks on that journey as a rationalist, is the temptation to view people as numbers. That's especially the case if those numbers are broadly positive, because they can cloak harsh realities on the ground.

The recovery may have been steady, month-to-month and year-to-year, but it was not consistent either demographically or geographically. Well-educated people heavily concentrated in large cities have prospered; large swaths of the heartland, where traditional manufacturing jobs are not coming back, feel left behind. So, too, do many Americans living in inner-city communities like the South Chicago ones in which Mr. Obama once toiled.

The President's defenders note that the income-inequality gap would have grown faster if not for measures he has taken – including, in addition to Obamacare, an extension of tax cuts for most Americans, coupled with hikes for those in the top bracket.

But there will always be room to wonder what might have been had he been a little less pragmatic. Maybe, tougher financial reforms would have caused more benefits to flow downward. Maybe, a more robust stimulus package could have invested further in such things as skills training, to give people on the margins a better shot at being closer to the new economy's heart.

And maybe it would have helped the mood had Mr. Obama communicated during the crisis and its aftermath with more urgency and empathy.

Dating back to his organizer days, he had some expectation that others would detach emotion from reason the way he can. When campaigning for re-election in 2012, he at times seemed to expect any thinking person to coolly recognize how much worse things would have been if not for his policies, and to share his confidence in the slow but steady march of progress, no matter what they were seeing firsthand.

That wasn't enough to cost him a second term. But it may help explain a common perception, in troubled corners of the Rust Belt that turned their backs on Hillary Clinton in 2016, that the Democrats were indifferent to their struggles.

On the campaign trail, alongside Hillary Clinton, in 2008.

And it may also explain why he was among the many world leaders caught off-guard by a public backlash against globalization, making a limited effort to ensure that Americans were sold on trade liberalization when his administration was negotiating the Trans-Pacific Partnership late in his second mandate. To Mr. Obama, the world was marching toward an ever-more global economy whether all Americans liked it or not. So, true to form, when he did make the public case for the trade deal that would have been one of his last legacy pieces, it was with a realist's argument that the TPP included practical measures – such as labour and environmental protections – that would better serve the U.S. than would trying to fight the inevitable.

Now, the TPP is dead in the water. And Americans have a president-elect who tells them he can make the world bend to his will, and who encourages supporters to rail against outside forces. Zing, boom.

A commitment to global engagement, but not at the price of entanglement

"Often, there are no good choices," Jerry Kellman said, when asked how the President's approach to global security lined up with his organizational philosophy. "Only ones that are relatively better."

The man who had once mentored the future president seemed to be drawing somewhat from one of Saul Alinsky's best-known rules for would-be radicals: "As an organizer I start from where the world is, as it is, not as I would like it to be."

For those who had romantic expectations of Mr. Obama as a global healer, which he did little to discourage on a grandiose international tour during the campaign that first brought him to power, it must be jarring that such realism more accurately came to reflect the way he subsequently governed.

Behind the scenes, Mr. Obama had his own, even more blunt way of describing his approach to foreign policy: "Don't do stupid shit."

No less than Ms. Clinton has implied that such a mantra indicates too little serious thought about America's place in the world. "Great nations need organizing principles," she said in 2014, "and 'Don't do stupid stuff' is not an organizing principle."

In fact, it very much did prove an organizing principle – albeit one entailing a sort of hyperpragmatism that, because it involved all but turning a blind eye to horrors like those that unfolded in Syria this past fall, produced probably the biggest stains on Mr. Obama's record.

A Syrian man walks past destroyed buildings on May 2, 2016, in Aleppo’s Bab al-Hadid neighbourhood.

He was not an isolationist president, of the sort his successor has intermittently threatened to be. On the contrary, at the diplomatic level, he favoured engagement whenever possible. The old community-organizer mentality very much had an echo in his inclination to extend a hand to people or entities that others would prefer to confront or avoid – literally (if symbolically) in his willingness to exchange pleasantries publicly with the likes of Venezuela's Hugo Chavez; much more consequentially in his controversial nuclear agreement with Iran and in the opening of relations with Cuba. On some of the biggest challenges facing the planet, such as climate change, he clearly believed the U.S. could lead.

But his foreign policy will largely be defined by his use of force, or lack thereof – especially in the Middle East and in South and Central Asia, where he inherited a pair of mismanaged wars and was confronted with escalating turmoil that carried security risks terrifying to many in his own country.

At a time when the excesses of the George W. Bush era had bequeathed lingering international bad will and domestic fatigue toward American interventionism, Mr. Obama was first and foremost wary of actions that could make incipient or ongoing problems worse. And when he did opt to engage, his search for the least-bad ("relatively better," per Mr. Kellman) choices usually led him to decisions that limited U.S. entanglement.

Sometimes, that required a steely willingness to take non-American lives, which complicated any humanitarian points he might get for ending the rendition and torture practices that existed under his predecessor. Under Mr. Obama's watch, the U.S. dramatically ramped up its reliance on counterterrorism drone strikes to take out human targets, most heavily in Pakistan; watchdog groups have put the civilian count from such strikes, each of which he is said to have personally approved, in at least the high hundreds.

Other times, it meant a willingness to engage in only a bare minimum of military engagement. When he sent American troops into Libya as part of an international coalition, convinced by more hawkish members of his administration – Ms. Clinton among them – that it was better than letting that country descend into civil war, he displayed little interest in nation-building. (Mr. Obama has since called the lack of planning for the day after Moammar Gadhafi was overthrown his "worst mistake.")

And in at least one disastrous case, it meant refusing to intervene in any meaningful way at all, even as a Syrian uprising to which he had lent rhetorical support during the 2011 Arab Spring culminated in the massacre of hundreds of thousands of people.

In Syria, there truly were no good choices. Given President Bashar Assad's Russian and Iranian backing, and the uncertainty of what might replace him, the uprising there had the makings, from the outset, of a quagmire. When Mr. Obama infamously backed away from his threat of military action if Mr. Assad crossed a "red line" by using chemical weapons – a climb-down facilitated by Russian intervention with Mr. Assad, which strengthened Vladimir Putin's hand across the region – the Islamic State was strong enough there to make it fraught to pick any side in what had become civil war. By the time Aleppo collapsed at the end of 2016, with civilians dying or fleeing as the once-great city was destroyed by Russian-backed Assad forces, even critics of Western inaction lacked much specific advice for a practical alternative to American passivity.

But the humanitarian disaster in Mr. Obama's final weeks on the job made the world, as it is, look truly ugly.

And while the best defence for his inaction is that the fallout might have been even worse had the President moved more ambitiously and aggressively, his determination to avoid greater destabilization outside Syria's borders did not seem to resonate domestically. Neither, for that matter, did the fact that fewer Americans died with him as commander-in-chief than likely would have been the case under a president more inclined toward trying to solve the world's problems – or reshape the world as he or she saw fit – by flexing military muscle.

Islamic State will be defeated in Mosul: Obama

His usual tendency to put everything in perspective, and his expectation that others were capable of doing likewise, again didn't help. In at least one instance, when he publicly referred to the Islamic State as a "jayvee team" – effectively dismissing it as a pale imitator (or junior-varsity version) of al-Qaeda – it reflected an underestimation of an enemy. Meanwhile, in an expansive examination of Mr. Obama's foreign-policy mindset earlier this year, The Atlantic's Jeffrey Goldberg reported that the President was fond of reminding staff that terrorism "takes far fewer lives in America than handguns, car accidents and falls in bathtubs." The facts bear that out, but to the extent that such cool rationalism slipped into public view, it no doubt convinced some Americans that he was indifferent to their fears.

Such fears were especially pervasive in his final year on the job, even though the Islamic State's terrorization of the United States during Mr. Obama's tenure amounted to a few lone-wolf actors that the group may have inspired. And his successor tapped into those fears, claiming that Americans had been insufficiently protected from the very clash of civilizations that many of Mr. Obama's relatively better decisions were aimed at avoiding.

As it turned out, America's citizens lacked an appetite for military adventurism, but struggled to abide the perceived global weakness stemming from its absence. No good choices.

Bridges built, bridges burned

"I didn't know whether he was confident," Alvin Love said recently, "or naive."

He was referring to 1985, and to what he made of the young community organizer wandering a dangerous neighbourhood a long way from where he had grown up, counting on his limited street smarts and powers of persuasion to keep him safe and to get locals to band together in their common interest. But Rev. Love could just as well have been talking about 2009, when Mr. Obama came to power in another town in which he lacked much experience, steadfast in his belief that he was capable of bridging divides by appealing to enlightened self-interest.

Sen. Barack Obama heads up the Senate steps to vote on a bill at the U.S. Capitol on Nov. 17, 2005, in Washington.

For all his clear-eyed realism on policy matters domestic and foreign, Mr. Obama was plainly too optimistic about making Washington a more harmonious place. His inability to do so makes for a grim dichotomy: A president who seemed to have unique potential to bring Americans together leaves office following a brutally polarizing election that replaces Mr. Obama with the most divisive candidate in the country's history.

In the speech that brought him into the national spotlight, at the 2004 Democratic National Convention, Mr. Obama famously pronounced, "There is not a liberal America and a conservative America; there is the United States of America!"

During his final State of the Union address last year, reflecting on two terms of congressional votes along strictly partisan lines, Mr. Obama publicly lamented his own role in proving that wrong. "It's one of the few regrets of my presidency – that the rancour and suspicion between the parties has gotten worse instead of better," he said. "There's no doubt a president with the gifts of Lincoln or Roosevelt might have better bridged the divide."

U.S. President Barack Obama meets with President-elect Donald Trump in the Oval Office of the White House in Washington, on Nov. 10, 2016.

Some of his old friends in Chicago offer a different take. If they have a criticism of how Mr. Obama wielded power, it's that he characteristically put too much trust early on in those on the other side of the aisle. From this perspective, he failed to make full use of the congressional majority he enjoyed in his first two years in office – compromising on economic plans and failing to aggressively move on social issues, such as gun control, that he would later identify as deeply important to him.

"I looked at him through that first term, and the fact that he didn't ram things through was typical Barack," says Loretta Augustine-Herron, recalling that when she volunteered for him with the Developing Communities Project, she sometimes grew impatient with his attempts at consensus. "My thing is, that's not always going to happen."

It would be tough to argue that Mr. Obama had willing dance partners in Washington. From the get-go, Republicans were loath to give him victories, voting as a bloc against any significant legislation he put forward; compromises he inserted into bills were dismissed as cover for socialist intentions. Pressure from the Tea Party, a populist protest group that came into being in the months after he took office, added to GOP legislators' fears of being seen by supporters as too open to him. After the 2010 midterm elections, the Republicans were armed with a congressional majority that included a new contingent of hardliners who would make their leadership pay for the slightest hint of softness.

As he is about to be succeeded by a man who spent much of Mr. Obama's presidency propagating a conspiracy theory that he is not an American citizen, there is no overlooking the role that bigotry played in some of the most vitriolic opposition to him. Much of the most vicious rhetoric during the Obama years played to perceptions of otherness; the uprising of the "white working class" that swung decisive battleground states in 2016 was tinged with nostalgia for a time when people who looked like him were kept further from positions of power.

I don’t know if anybody could’ve lived up to the expectations that the African-American community had for Barack Obama – you’d have had to be Jesus, almost.

Alvin Love, a pastor who first met Mr. Obama in Chicago in 1985

Underlying all that were polarizing factors against which any president might have been powerless. Among them were a new media landscape that allows voters to exist in informational silos in which they consume only news coverage that reinforces their views, and congressional maps so gerrymandered to protect incumbents that those seeking re-election have to worry more about true believers who vote in parties' primaries than they do about general-election voters.

But there were also persistent suggestions that, faced with opposition less pliant than he had hoped for, Mr. Obama threw up his hands faster than he should have.

He did not take to D.C.'s culture of after-hours schmoozing and deal-brokering the way other presidents had, although friends point to that as a matter of prioritizing his young family, after growing up with an absent father himself. "He was not out slapping backs at night – he was at home helping his daughters with their homework," Arne Duncan, who served as Mr. Obama's education secretary after going back a long ways with him in Chicago, told me.

Malia Obama walks her new six-month old Portuguese water dog Bo alongside US President Barack Obama, Sasha Obama and First Lady Michelle Obama on the South Lawn of the White House in Washington, DC, on April 14, 2009.

Others, not just Republicans but a fair number of Democrats, have accused Mr. Obama of thinking he was above it all – his long-held suspicions that most politicians are creatures of self-interest manifesting itself in a disinclination to stroke the egos of people unprepared, in his view, to act for the common good.

If the level of effort Mr. Obama put into postpartisanship in his first term is debatable, it's clearer that he had almost completely given up on it by his second. Starting even before he was re-elected and ramping up thereafter, he tried less to persuade Republicans to go along with his agenda, and more to find ways to work around them – relying on executive power more unabashedly than many of his predecessors, with a "We can't wait" public-relations campaign touting efforts to bypass an obstructionist Congress.

A few high-profile executive orders – on Cuba-U.S. relations, the Iran nuclear deal, the shielding of millions of undocumented immigrants from deportation (blocked by a Supreme Court evenly divided because Republicans denied Mr. Obama his right to appoint a replacement for the late Antonin Scalia) – garnered the most attention. But more unusual was the extent of the President's reliance on comparatively under-the-radar regulations – 560 significant ones, by The New York Times's pre-election count. In keeping with his usual taste for incrementalism, he quietly beefed up everything from environmental standards to human-rights provisions, labour rules to consumer protections.

The downside was twofold: Not only will Mr. Trump be able to quickly reverse many of Mr. Obama's policies using the same mechanisms, but he will be able to point to precedent if he overuses executive power himself.

It's also fair to wonder, now, if a sort of siege mentality conspired with the realities of the information age to lead Mr. Obama to sometimes distance his administration from the public in a way that contributed to mistrust. To put it mildly, he failed to make good on his promise, made on his first day in office, to create "an unprecedented level of openness in government."

Last year, the Associated Press reported that, under his watch, the government set a new record for rejecting Freedom of Information requests – censoring or rejecting requests for government records in 77 per cent of cases. In response to the disclosure of sensitive information by the likes of Edward Snowden and Chelsea Manning, Mr. Obama launched, by executive order, an Insider Threat Program that aimed to stop leaks by asking federal employees to report suspicious activities on the part of co-workers, and to base such reports on dubious behavioural-profiling techniques.

Meanwhile, even as he lamented how media silos perpetuate political polarization, Mr. Obama limited his press availability, giving primary access to sympathetic outlets.

That's much different from what he was like when he first entered politics. Todd Spivak, who as a Chicago reporter covered Mr. Obama more closely than any other journalist during his Illinois senate days, and who was often critical of him, recalled him being unusually accessible even for a state politician. "I think, as journalists, we were all let down by this pledge to transparency," Mr. Spivak said by phone from Pittsburgh, where he now lives. "And certainly that stood in contrast to my experience covering him, when I thought he was very accessible to the press."

Barack Obama, candidate for a Senate seat in Illinois and one of the keynote speakers of the 2004 Democratic National Convention, addresses delegates during the second night of the event at the FleetCenter in Boston, July 27, 2004.

Not that any of this necessarily bothered people otherwise inclined to support Mr. Obama. While continuing to be loathed by the Republican base, his approval ratings as he leaves office are well above 50 per cent, higher than those through most of his presidency.

Perhaps he was naive to think bridge-building was what even many of his own backers wanted. Though those high approval scores no doubt also have something to do with an appreciation – especially given the majority of voters' apprehensions about what is coming down the pike – that, even if he didn't deliver on his postpartisan promise, Mr. Obama nonetheless conducted himself more gracefully and with much less scandal than have most other modern presidents.

That matters as much to some of his old friends as do any specific policy achievements or failings, because it was important for communities like theirs that he led by example and proved his doubters wrong.

A leader by example, but a legacy in doubt

Johnnie Owens, who still works as a local organizer in Chicago, was nervous back when his old friend took office.

For his country's first African-American president, there was so little room for error. Appearing to be in over his head early on, looking overwhelmed by whatever was thrown his way, getting mired in scandal – any of the things that have befallen far more experienced and nationally tested politicians who have taken the office – would have provided fodder to the "I told you so" skeptics.

Eight years later, whatever criticisms can be thrown at Mr. Obama, nobody who was ever willing to give him a chance in the White House can reasonably say he looked or acted as though he didn't belong there.

U.S. President Barack Obama waves as he leaves the podium after speaking to journalists during his last news conference of the year at the White House, on Dec. 16, 2016.

Whether responding to economic meltdown or terror attacks or to a level of partisan vitriol few other presidents have faced, he was cool and collected. There was not a whiff of personal impropriety, and his administration was relatively free of the hangers-on that have brought others into disrepute. He boasted what could only be described as a model family, with a spouse who went from a reluctant to a beloved First Lady. Unlike his immediate predecessors, the bumbling Mr. Bush and scandal-plagued Mr. Clinton, he elevated his office simply by the manner in which he conducted himself.

To listen to people who were around him when it all started on the South Side's much smaller stage, the way that he led by example on the national one was far from a trivial or purely aesthetic matter. Rather, it was part of Mr. Obama's meeting his promise to fellow organizers those many years ago that he would be able to do more for their community if he were sitting on the other side of the table.

By more tangible measurements, his fulfilment of that promise is tenuous. Neighbourhoods where he organized in the eighties, and which he later represented as a state-level politician, had a brutal 2016 – contributing to jaw-dropping Chicago crime numbers, including more than 750 homicides, that speak to everything from bad schools to broken families to terrible citizen-police relations. Talk to young community activists now working the same streets he once did, and you will hear complaints that, while pursuing lofty national and international goals, President Obama failed to move with urgency to address crises in his former back yard.

And although defenders counter that the South Side (along with other impoverished areas of the country) stood to reap long-term benefit from Mr. Obama's social policies, many of those policies have been imperilled by November's surprising election result. As recently as the fall, someone like John Bouman – who heads the Chicago-based Sargent Shriver Center on National Poverty Law, which takes on legal-aid cases that might force policy changes to help the poor, and who considered Mr. Obama a strong ally during his state-senate days – could confidently describe the Affordable Care Act as "probably the biggest single thing to address poverty in America since the 1960s." Now, with a Republican stranglehold on power, nobody knows if Obamacare will survive 2017, or in what form.

But once upon a time, when he was trying to build from the ground up, the journey mattered more than the destination. The few small victories won by organizers, and the many defeats they faced when they ran into seemingly immovable forces, were less important than the experience gained as community members learned to stand up for themselves in ways that would eventually make for brighter futures.

It would be absurd to apply exactly the same criteria to eight years as the most powerful person in the Western word. And yet even when it looked as though Mr. Obama's preferred successor would replace him – when they could have cited any number of policy accomplishments – Mr. Owens and others once close to the President zeroed in on his influence on younger African-Americans, when discussing what made them proudest of his time in office.

"His presidency has been a boon for our children," Ms. Augustine-Herron said, "because it lets them know they can be who they want to be."

The President acquiesced to a selfie with 11-year-old Jacob Haynes and four-year-old James Haynes after taking a family photograph with departing White House staffer Heather Foster.

Rev. Love qualified that notion a bit. Some of the young adults in his parish are jaded, he said, by unmet expectations. ("I don't know if anybody could've lived up to the expectations that the African-American community had for Barack Obama – you'd have had to be Jesus, almost.") But the preteens adore him, and the teenagers respect him. And that can change how they see themselves – or, never having grown up in a world in which someone like him couldn't be president, has spared them some of the barriers that previous generations grew up with.

As last year's frequently nasty election demonstrated, Mr. Obama didn't make everyone in his reach their best selves; not even close. But maybe first by winning the White House, then by retaining moral authority through his time there, he did empower people – not just African-Americans, but others who might have felt marginalized by their skin colour or sexual orientation or social status – to carry on fighting to advance issues they care about, beyond where he was able to take them.

Even that sort of legacy, of course, is complicated by Mr. Trump, who boasts almost none of Mr. Obama's equanimity and who appealed in a significant measure to those who believe visible minorities already have too many advantages. But it is possible that Mr. Obama will soon be elevated further, in perception, by what follows him. And if the impending ascension of Mr. Trump shakes Mr. Obama's own optimism a bit, it might cause him to double down on his faith in himself to defy the pessimists by bringing others together in common purpose, rather than moving on.

In a follow-up e-mail exchange after the election, Jerry Kellman suggested that the President – like Mr. Kellman himself, and others "committed to justice" – had underestimated "a deep underbelly of greed, narcissism and hatred."

"Because of this," he predicted, "Barack will choose a far different retirement than he otherwise might have."

Based on Mr. Obama's recent hints, that likely will involve remaining in the political arena more than have most ex-presidents – challenging Mr. Trump where he sees fit, and leading a pushback against the gerrymandering of congressional districts that has both benefited Republicans and contributed to the polarization of the electorate.

It will also likely see him being more hands-on, in Chicago's South Side and places like it, than he has been in a long time. One vehicle for him to do so, which he has already indicated he will make use of, is My Brother's Keeper – a primarily privately funded initiative launched by the White House in 2014 to help direct resources toward young men of colour.

Even after eight years running the country, there will be no shortage of work in its communities and on its streets.

On the day I visited Rev. Love, a voice called out as I approached the church's door. It was a young man looking for a handout, the kind of guy the President was mistaken for 30-odd years ago.

The neighbourhood, the pastor said, really has improved. But nobody, least of all Barack Obama, ever promised it would be quick or easy or smooth. Deep breath. Start over.

President Barack Obama boards Air Force One at Yangon International Airport for departure from Myanmar en route to Australia, Nov. 14, 2014.


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