Greg Jaffe is a national security reporter for The Washington Post, where he has been since March 2009. Previously, he covered the White House and the military for The Post.

(Pete Marovich/Bloomberg)

Few political careers and presidencies have been more defined by speeches than Barack Obama’s. His 2004 speech at the Democratic National Convention vaulted him into the country’s consciousness. His 2008 speech on race saved his faltering presidential campaign. As president, Obama’s biggest and most consequential moments — his unfulfilled outreach to the Muslim world in Cairo, his Nobel Peace Prize address on the grim necessity of war in Oslo and his eulogy for nine slain parishioners in Charleston, S.C. — often have been speeches.

Obama’s best oratory is beautifully written, meticulously crafted and theatrically delivered. It is a record of our fears, flaws, shortcomings and accomplishments. “I don’t know of any president who has put that kind of work into his speeches,” says Douglas Brinkley, a presidential historian. “He organizes his thinking by putting pencil to pad.”

In a few days, Obama will deliver one of his last big speeches as president. In a bit of clever stagecraft, he is scheduled to speak at the Democratic National Convention in Philadelphia on the 12th anniversary of his electric 2004 convention speech. The moment raises a question that cuts to the heart of Obama’s presidential legacy and our polarized politics: Which Obama address will still sound wise and inspiring when our bitter, partisan disputes have faded from memory?

In just 272 words, Abraham Lincoln’s remarks at Gettysburg redefined the purpose of the country. John F. Kennedy will forever be remembered for his inaugural address: “Ask not what your country can do for you; ask what you can do for your country.” His challenge is all the more poignant because of his sacrifice. Ronald Reagan seemed to be bending the arc of history when he stood at Berlin’s Brandenburg Gate and spoke directly to the Soviet leader: “Mr. Gorbachev, tear down this wall!”

So which Obama speech, if any, will schoolchildren read decades from now?

To answer the question, I quizzed Republicans, Democrats, historians, and some of the president’s longest-serving and most loyal aides. I pressed for clues on the president’s preferences. Which speech would Obama pick? Could that be the one? Peering into the future is an impossible task, and there was more argument than consensus among those I spoke with. But the conversations led me inexorably to one speech. First, let’s review the contenders:

 

‘There’s not a liberal America and a conservative America; there’s the United States of America.’

Among Obama’s staff in the West Wing, his 2004 convention speech is thought to be the one that will endure.

At the time Obama delivered it, he was running for Senate, but he was a virtual unknown, with a name — Barack Hussein Obama — that evoked the country’s enemies. He framed his biography as proof of America’s exceptional nature: He was descended from a Kenyan cook, a Kansan who marched with Patton’s Army and parents who believed “that in a tolerant America, your name is no barrier to success” and that “in a generous America, you don’t have to be rich to achieve your potential.”

Even more memorable, Obama rejected political polarization as a false byproduct of a dysfunctional Washington: “There’s not a liberal America and a conservative America; there’s the United States of America. There’s not a black America and white America and Latino America and Asian America; there’s the United States of America.”

The convention keynote, which Obama wrote without a speechwriter, later became a kind of ur-text inside his White House. Whenever the president’s speechwriting team was struggling, David Axelrod, Obama’s senior adviser and friend, would urge them to re-read the 2004 address. Axelrod calls it “Obama’s love letter to America.” Jon Favreau, the president’s lead speechwriter during his first term, has one of the speech’s most famous lines hanging on the wall in his Los Angeles apartment: “In no other country on Earth is my story even possible.”

The speech, though, has its flaws. Its middle sections are bloated by Democratic boilerplate and a tribute to John Kerry, then the Democratic Party’s lackluster presidential nominee. And the speech already reads as somewhat wistful. “It’s an evocation of what could be but is sadly and tragically a myth,” says Jeff Shesol, a speechwriter in the Clinton White House. “Obama’s whole presidency is a rebuttal of that speech.” Indeed, Obama backed away from some of its most optimistic notes in his last State of the Union address. “It’s one of the few regrets of my presidency that the rancor and suspicion between the parties has gotten worse instead of better,” he says.

 

‘The anger is real; it is powerful; and to simply wish it away, to condemn it without understanding its roots, only serves to widen the chasm of misunderstanding that exists between the races.’

Sometimes a flash of high drama gives a speech extra staying power. Obama’s 2008 race speech, written after video surfaced of his former pastor cursing America, represents such a moment. Obama was fighting for his political life and delivered a personal speech that was unlike anything most Americans had heard before.

Obama’s mixed-race background allowed him to speak bluntly to black and white Americans. “This was the speech he was born to give,” Shesol says. Obama urged whites to empathize with his pastor, the Rev. Jeremiah Wright, who had served as a Marine and had come of age during segregation. And he prodded blacks to reflect on his white grandmother, who feared black men she passed on the street and who sometimes spoke in terms of racial stereotypes that made him cringe. “These people are a part of me,” Obama said, “and they are part of America, this country that I love.”

In the anguished final months of Obama’s presidency, marked by angry protests, police shootings and inflammatory political rhetoric, the 2008 speech still reads true. “The speech didn’t solve anything,” says Ted Widmer, a former Clinton administration official and professor at Brown University, “but it explains deeply and at a high level how complicated race can be.”

 

‘As a nation, out of this terrible tragedy, God has visited grace upon us, for he has allowed us to see where we’ve been blind.’

Historians tend to search for “the speech” — the one that will endure — among the eulogies that Obama gave after the mass shootings and terrorist attacks that took place with deadening regularity over the course of his presidency. “Obama put his whole soul into those speeches,” Brinkley says.

All presidents at some point play the role of minister. Reagan lived up to the moment with a simple but moving speech consoling schoolchildren and adults after the Challenger space shuttle explosion. Bill Clinton spoke eloquently after the Oklahoma City bombing. But no president has played this role like Obama, who has done it again and again and again — in Tucson, in Newtown, in Dallas.

Brinkley imagines that an anthology of Obama’s memorial speeches would offer future generations insight into today’s America. And of those speeches, the president’s Charleston eulogy, following the killing of nine parishioners at Emanuel AME Church, stands out for its eloquent meditation on God’s grace and the surprise of a president singing a Christian hymn. “It is the one seared in the public’s memory,” Brinkley says.

Obama cast the Charleston killings as a divinely inspired turning point. In the days after the attack, South Carolina lawmakers voted overwhelmingly to remove the Confederate battle flag from the state capitol dome. The country, Obama said, had responded to the brutal killings with a “big-hearted generosity and . . . a thoughtful introspection and self-examination that we so rarely see in public life.”

He called on the nation to build on that spirit by reforming gun laws, tackling poverty and passing criminal justice reform. But all of those efforts stalled. The Charleston mass shooting — shocking and tragic in the moment — faded quickly from memory like the others that had come before and those that would follow.

 

‘It was not a clash of armies, but a clash of wills; a contest to determine the true meaning of America.’

The most famous presidential speech — the standard by which all other White House oratory is judged — is Lincoln’s Gettysburg Address. In it, Lincoln consecrated the site of one of the Civil War’s bloodiest battles and sought to unite all Americans, Northerners and Southerners, with a common vision. The speech elides details, mentioning no names of the dead and offering no account of the devastating battle. Lincoln completely avoids the topic of slavery. Instead he uses the speech to recast American history, elevating equality over liberty as the country’s most important idea. The Pulitzer Prize-winning historian Garry Wills describes Lincoln’s brief remarks that day as “one of the most daring acts of open-air sleight-of-hand ever witnessed by the unsuspecting. Everyone in that vast throng of thousands was having his or her intellectual pocket picked.”

Obama’s speech last year commemorating the 50th anniversary of the brutal beating of marchers in Selma, Ala., performed a similar feat. At Selma, Obama consecrated ground, placing the events on the Edmund Pettus Bridge on par with those in Concord, Lexington, Appomattox and Gettysburg. Like Lincoln, Obama rewrote American history, putting rebels, protest leaders, misfits, artists and immigrants at the center of the story. “Look at our history,” he implored. “We are Sojourner Truth and Fannie Lou Hamer, women who could do as much as men and then some.” His litany of American heroes included the “Lost Boys of Sudan,” “the hopeful strivers who cross the Rio Grande,” “the slaves who built the White House” and “the gay Americans whose blood ran on the streets of San Francisco and New York.” America’s founders and the “fresh-faced GIs” of World War II merited only passing mentions. For the first time, they were relegated to the periphery.

Obama’s 2004 convention speech was more of a surprise. The stakes were much higher when he delivered his 2008 race speech. His Charleston eulogy packed more pathos. But the Selma speech, written over the course of five drafts, was the most ambitious and radical speech of his presidency.

Obama described an America that is constantly changing, chronically dissatisfied and forever striving to realize the ideals laid out in its founding documents. “What greater expression of faith in the American experiment than this?” Obama said at Selma. “What greater form of patriotism is there than the belief that America is not yet finished, that we are strong enough to be self-critical, that each successive generation can look upon our imperfections and decide that it is in our power to remake this nation to more closely align with our highest ideals?”

Even in today’s fractious times, the Selma speech wins praise from both Republicans and Democrats. “It falls into the category of speeches that every child should read in school,” says Michael Gerson, the lead speechwriter for President George W. Bush and now a Washington Post columnist.

Aides say the Selma speech is also Obama’s favorite address, because it most clearly expresses his view of American exceptionalism — a topic he first explored 12 years ago in his convention speech.

But Selma’s true genius lies in its ability to speak to America’s future. The Census Bureau projects that the U.S. population will become “majority minority” in 2044. The shift has fueled anxiety among whites and has probably given a boost to Republican nominee Donald Trump’s “make America great again” campaign for the White House. It has spawned some of the backlash against Obama’s presidency, along with questions about his legitimacy to serve, his love of country and his faith.

Someday, though, this demographic shift will be seen as an inevitable part of the American story. Selma is the first, great presidential address to speak to that America and a speech only our first black president could give.

Selma is the one.

 

Reader poll: Obama's most memorable speech

This is a non-scientific user poll. Results are not statistically valid and cannot be assumed to reflect the views of Washington Post users as a group or the general population.