November 4, 2008 was an unusually warm day in Chicago, with a high of 71, a near-record temperature. That had something to do with the joy, the people strolling in the street on Michigan Avenue after Barack Obama's acceptance speech in the front yard of the city where he started out, the people on top of one of the Mag Mile's giant planters singing "This Land Is Your Land" to us as we walked by.

Every other time I've been in a crowd in the street on Michigan Avenue since then has been because of a protest. "This Land Is Your Land" and "Whose streets / our streets" are both the same sentiment and the opposite. I heard the latter the next time I walked those streets, for hours, covering the NATO protests, in which many people who voted for him surrounded McCormick Place in objection to both his foreign and domestic policies: unity against, not with.

Still Obama returned to close out his presidency in Chicago. The weather is a hoary trope, but it was hard not to notice the contrast. Yesterday brought a grim January rain, followed by winds strong enough to cancel flights and the president's planned helicopter trip from O'Hare to McCormick Place. It was the day Dylann Roof was given the death penalty for the mass shooting at Mother Emanuel, the subject of one of Obama's saddest, most uplifting speeches.

Eight years ago, his voters were afraid. A month after the speech, the National Bureau of Economic Research noted the obvious, that the country had been in a recession for a year; a few days before his inauguration, economist and columnist Paul Krugman foresaw something that would look more like the Great Depression.

"For even as we celebrate tonight, we know the challenges that tomorrow will bring are the greatest of our lifetime. Two wars, a planet in peril, the worst financial crisis in a century," Obama said. "The road ahead will be long. Our climb will be steep. We may not get there in one year or even in one term. But, America, I have never been more hopeful than I am tonight that we will get there."

Eight years later he came home to warn America about itself.

"That's what I want to focus on tonight. The state of our democracy," Obama said. "There have been moments throughout our history that threatened that solidarity. And the beginning of [this] century has been one of those times." The bill of particulars he laid out is familiar, each contributing to his heir-apparent's loss: economic inequality, globalization, terrorism. He rhetorically countered it with the receipts from his own tenure, making the case that they are considerable in the context of 2008: an unemployment rate lower than when he took office, the Affordable Care Act, the killing of Bin Laden. Yet he faced an audience and a country seemingly just as—or more—fearful than the one he faced in Grant Park.

It is the paradox of his administration: that the incrementalist No-Drama Obama, having made substantial progress—not necessarily the kind of progress his foes or even many of his fans wanted, but the sort that could reasonably be expected based on his political career, and which got him elected twice—would exit his presidency less fearful of external threats to our democracy than of threats to the foundation it rests upon.

"If there is anyone out there who still doubts that America is a place where all things are possible, who still wonders if the dream of our founders is alive in our time, who still questions the power of our democracy, tonight is your answer," Obama began his Grant Park speech. Those doubts and doubters haven't been resolved. "There will be setbacks and false starts," he warned. By 2016, it became, "For every two steps forward, it often feels we take one step back."

What happened? Obama's hope, his implicit and explicit promise that all things are possible, was always in contention with his actual approach to governance. That all things are possible through compromise is a contradiction in terms. For all the ways Obama was historically unprecedented, he offered, and continues to offer, a belief in an idealized form of traditional American politics. Eight years of watching its failures and successes will be followed by at least four years of something that, at least right now, seems as far away from that tradition as ever before. In retribution, frustration, or desperation, Americans narrowly elected a man who promises that all things are possible without compromise.

Perhaps that man has a point. The president-elect, who built a political following with baseless questions about the sitting president's status as an American, will get to appoint a Supreme Court justice because his party, for months, ignored exactly the sort of political norms Obama championed in his farewell address. "How do we excuse ethical lapses in our own party but pounce when the other party does the same thing?" he asked last night.

How? You just put your lips together and blow.

"As Lincoln said to a nation far more divided than ours, we are not enemies but friends. Though passion may have strained, it must not break our bonds of affection," Obama said in Grant Park. With those bonds more frayed, his opponents having swept the election using the opposite of the political ideals he outlined, this time Obama asked for mere empathy: "But, if our democracy is to work the way it should in this increasingly diverse nation, then each one of us need to try to heed the advice of a great character in American fiction, Atticus Finch, who said you never really understand a person until you consider things from his point of view. Until you climb into his skin and walk around in it."

But Finch, depending on how you view these things, is two characters, not one, and more recently he emerged into his darkest timeline. In the controversial 2015 release of To Kill a Mockingbird's first draft, Go Set a Watchman, Atticus is a paternalistic segregationist, and its publication highlighted the fissures and limits of the world described in Lee's great work, not only in terms of his relationship to blacks but to poor whites as well, breaking readers' bonds with one of America's archetypal symbols of hope, the past returning to rewrite the present

What did things look like from Obama's point of view as he said goodbye? Hopeful, still; as my friend Robin Amer put it, the speech was literally the audacity of hope. And he found that hope ("I leave this stage tonight even more optimistic about this country than when we started") in the most profound yet quotidian form of the future, the replacement of one generation by another.

"Let me tell you, this generation coming up—unselfish, altruistic, creative, patriotic—I’ve seen you in every corner of the country. You believe in a fair and just and inclusive America. You know that constant change has been America's hallmark, that it is not something to fear but something to embrace," he said. "You'll soon outnumber all of us, and I believe, as a result, the future is in good hands."

This hope is a hard thing to square with the past, distant and immediate, a past that so often rewrites the present as a protest against the future. Obama tried to do so, as much as he could, in one of his longest and most difficult and ambitious speeches, "A More Perfect Union"—a phrase that is itself a contradiction in terms—a 2008 address on race in America which has the audacity of finding the seeds of a perfect union within the original sin of slavery. In it, he borrows another contradiction from another fictional lawyer created by another race-haunted white southerner, William Faulkner: "The past is never dead, it's not even past." It's a contradiction within a contradiction, the past always in compromise with the present. Obama accepted that compromise and embodied its paradox—one that is hard to hold onto for long.