“It’s a fool’s errand you’re involved in,” warned Pulitzer Prize-winning historian Gordon Wood when approached recently by this magazine to predict Barack Obama’s historical legacy. “We live in a fog, and historians decades from now will tell their society what was happening in 2014. But we don’t know the future. No one in 1952, for example, could have predicted the reputation of Truman a half-century or so later.”

Wood is right, of course. Historians are experts on the past, not the future. But sometimes the wide-angle perspective they inhabit can be useful in understanding the present. And so, on the eve of Obama’s penultimate State of the Union address, we invited a broad range of historians — academic and popular — to play a game.

Over the past few weeks, New York asked more than 50 historians to respond to a broad questionnaire about how Obama and his administration will be viewed 20 years from now. After the day-to-day crises and flare-ups and legislative brinkmanship are forgotten, what will we remember? What, and who, will have mattered most? What small piece of legislation (or executive inaction) will be seen by future generations as more consequential than today’s dominant news stories? What did Obama miss about America? What did we (what will we) miss about him?

Almost every respondent wrote that the fact of his being the first black president will loom large in the historical narrative — though they disagreed in interesting ways. Many predict that what will last is the symbolism of a nonwhite First Family; others, the antagonism Obama’s blackness provoked; still others, the way his racial self-consciousness constrained him. A few suggested that we will care a great deal less about his race generations from now — just as John F. Kennedy’s Catholicism hardly matters to current students of history. Across the board, Obamacare was recognized as a historic triumph (though one historian predicted that, with its market exchanges, it may in retrospect be seen as illiberal and mark the beginning of the privatization of public health care). A surprising number of respondents argued that his rescue of the economy will be judged more significant than is presently acknowledged, however lackluster the recovery has felt. There was more attention paid to China than isis (Obama’s foreign policy received the most divergent assessments), and considerable credit was given to the absence of a major war or terrorist attack, along with a more negative assessment of its price — the expansion of the security state, drones and all. The contributors tilted liberal — that’s academia, no surprise — but we made an effort to create at least a little balance with conservative historians. Their responses often echoed those from the far left: that a president elected on a promise to unite the country instead extended the power of his office in alarming, unprecedented ways. Here, we have published a small fraction of the answers we found most thought-provoking, along with essays by Jonathan Chait, our national-affairs columnist, and Christopher Caldwell, whom we borrowed from The Weekly Standard. A full version of all the historians’ answers can be found here.

“Interesting stuff happens in the fourth quarter,” Obama told his Cabinet last month, shortly after his surprise announcement about restoring diplomatic relations with Cuba. As it happens, this was exactly what a few of our respondents had nominated as the best remaining action Obama could take for his legacy. Before going to press, we let them revise their answers. There will certainly be more interesting stuff, of Obama’s design and not, before January 2017 that will date this project over and over. History is funny that way.

Obama’s bark is worse than his bite: He issued 147 executive orders in his first term, compared to Bush’s 173 and Clinton’s 200. Nevertheless, Obama’s rhetoric on executive orders has been so polarizing — “Where I can act without Congress, I’m going to do so.” — that he has inflamed his opponents and strengthened their resolve to reverse his achievements. Just as the Supreme Court unanimously rejected Obama’s efforts to use recess appointments, so it could reject his immigration orders. Throughout history, unilateral presidential actions designed to circumvent Congress have led to pushback in the Courts and Congress that have ultimately undermined, rather than strengthened, the president’s legitimacy.

Many of the young people energized by Obama’s 2008 campaign subsequently became victims of the Great Recession — a devastating event for many young people — and grew disillusioned with politics; this prevented Obama from permanently attaching millennials to the Democratic Party.

I suspect that future historians are likely to focus on the rising inequality in the American economy during the Obama years, the deepening precariousness experienced by people who once anticipated a greater level of security and prosperity, and on the poisonous impact this has on the entire American political system. The crash of 2008 and its aftermath may come to be seen as a moment when greater reform was possible — a resolution to the crisis that placed greater weight on holding the financial system accountable and on aiding middle-class people who were hurt, as well as a chance for the deeper reassessment of the basis of the American economy, an opportunity to pursue policies that could have restored a greater level of equality. This didn’t happen, and it’s the great missed opportunity of the Obama presidency.

So-called transformative presidents forge lasting coalitions for their political party, shape a coherent and distinctive agenda of public policy, and rebuild institutions in ways that perpetuate their coalition and their policy agenda. Crucial to all of this is a public philosophy that gives meaning to the president’s political vision and Constitution understanding. Obama has no public philosophy, save a commitment to pragmatism — a kind of anti-public philosophy. This does not mean that Obama will be regarded as an unsuccessful president. His successes, however, are all pragmatic supplements to prior transformations rather than elements of a new and lasting political coalition or constitutional vision.

His contributions were sometimes remarkable, but Obama’s primary legacy is his destruction of political idealism for the foreseeable future. He proved an impressive steward of the traditions of his party since the 1970s. Where Obama differed was his brief but unforgettable achievement of a surprisingly large consensus around a belief — or delusion — that Americans rarely entertain. Put simply, it was that American politics could and must fundamentally change. The energies he conjured will not reappear soon and are less likely to do so because he summoned them for so ordinary and predictable a set of policies.

It is difficult to see how his presidency can be viewed as “transformative” when so many of his policies represented a continuation of the past rather than a break.

His great appeal as a candidate was that he was not interested in traditional politics. That quality, inevitably, has not helped him in Washington. He seems to have the rhetorical and conceptual tools necessary to use the “bully pulpit” power to great effect. Forging a popular coalition, however, requires a galvanizing inspirational agenda. His policies were too moderate to electrify the public.

What buoyed his aspirations was not a program but a dream that in his person, the people might come together and shape politics to their will and common aspirations. That was what the “we” in the brilliant “Yes We Can” slogan in the 2008 campaign was essentially about. He has not called the nation to new feats of “courage” (Kennedy), to make “war” on poverty (Johnson), even to “dream” more freely than ever before (Reagan). What Obama’s words have called for is for Americans to be the people they already are.

He was most effective as a “normal” president, and he helped put the presidency back on a human scale. He was a devoted and involved father, a loving husband, a man with acknowledged (albeit minor) vices, and someone who made it clear that he did not regard himself as omniscient. As president, he showed that effective governing requires careful deliberation, discipline, and the willingness to make hard and imperfect decisions, and he let us all watch him do just that. Even when one disagreed with his choices, one knew that his acts were never impulsive or cavalier. Future historians will give him full marks for that.

Obama’s efforts on behalf of women and girls are one of the least understood or commonly overlooked aspects of his presidency. From creating the White House Council on Women and Girls to appointing two women to the Supreme Court and a strong team of women leaders to his Cabinet and White House staff, Obama has taken concrete steps to ensure that women’s voices are heard. He has expanded economic opportunities for women, fought pay discrimination, increased women’s access to quality and affordable health care, worked toward combating sexual assault on college campus and in the military, and expanded services for victims of domestic violence and their children.

Here is one historic trend-break that has occurred during the Obama administration that has major significance for the well-being of African-Americans: the beginnings of a decline in the national prison population, after decades of expansion. The Obama administration deserves a fair share of credit. In 2010, Obama signed the Fair Sentencing Act, reducing prison time for convictions involving crack cocaine. Under Attorney General Eric Holder, sentencing guidelines were made retroactive, leading to the release of thousands. To date, the reductions have been small compared to the total incarcerated population, but the reversal is historic, and its disproportionate significance for African-Americans is evident.

Bill Clinton had the brilliant insight that the Democratic Party could win elections by transforming itself into the Republican Party. Obama might have tried to pull the party back to its New Deal roots but chose not to do so. He will be seen as having had little lasting impact on his party’s identity. The coalition that swept him to power has come apart, largely because it was not undergirded by any clear long-term strategy or goals.

We won’t get a full reckoning of the impact of administrative changes at federal agencies for a while. But here are some hints. Look at the Department of Justice. During the George W. Bush years, many veteran staff attorneys — Republican and Democrat alike — left or were pushed out during a period of intense politicization. The DOJ had arguably never been as partisan as it was during the Bush years. Obama, by contrast, appointed many highly regarded professionals. Those appointees have professionalized the hiring process and reinvigorated many of the DOJ’s divisions. A similar process has played out in the Department of Housing and Urban Development and the Department of Labor.

It is too soon to say right now what will come of Obama’s “pivot” or rebalancing of American foreign policy to Asia — but for sure, historians will see that during Obama’s administration, the old China policies of the past four decades were quietly, gradually put to rest.

Perhaps Obama’s least-heralded achievement was his effort to prepare the country for its future as a genuinely multiethnic and multicultural society. People of color will soon outnumber white Americans, religious diversity continues to grow, and differences in sexual orientation are increasingly accepted. Obama’s presidency may one day be seen as a watershed in the construction of a genuinely “rainbow” America. But then there’s Ferguson.

One part of Obama’s first term that’s been almost entirely forgotten already is his tepid endorsement of the Employee Free Choice Act, which helped to consign it to failure and with it any chance for a broadscale revival of the labor movement in the wake of the 2008 financial crisis. The continued implosion of the labor movement — especially marked by the assault on public-sector unions, one of the only remaining areas of union strength — will likely be seen as one of the major trends of these years, and Obama’s failure even to treat this as a major problem will be recognized as one of the defining qualities of his style of centrist politics.

Obama also put the leash back on overt U.S. military action just as it approached its breaking point under George W. Bush. That he did so in the interests of relegitimation rather than transformation (for example, releasing the torture memos but failing to prosecute the torturers) sets us up for an uncertain future or, worse, a new round of dirty wars. But this ambivalence might be regarded as a kind of achievement—one that is not always understood by an analysis that sees Obama’s national-security approach as simply an extension of Bush-Cheney.

Obama’s subsequent policy and vision has not only failed to rise to the level of his own insights into the inadequacy of American military and police power as the leading edge of government in a world plagued by fear and want; it has run in the opposite direction. From assassination by drone, to sustaining and augmenting an inhumane deportation regime, surpassing 2 million persons and counting, to the crackdown on whistleblowers and press freedoms, to the funneling of “excess” U.S. military hardware into local police departments, the militarization and overpolicing of American life proceeds apace.

I was struck by a passage from Dreams From My Father written by the pre-presidential Obama, after 9/11. The conflict between “worlds of plenty and worlds of want,” he writes, “twists the lives of children on the streets of Jakarta or Nairobi in much the same way as it does the lives of the children on the South Side of Chicago.” Failing to understand this, the powerful needlessly intensify a destructive spiral with their “dull complacency … unthinking applications of force … longer prison sentences and more sophisticated military hardware.”

President Obama’s actions suggest that he is truly passionate about climate change in a way that we haven’t fully grasped. Clearly he hasn’t done enough. But it’s important to consider how little political incentive Obama has had to do anything. Obama could have easily gotten away with talking soberly about the issue but never really doing anything about it. Instead, he’s done a lot: tough EPA constraints on coal, a meaningful accord with China to cut emissions, serious stimulus spending on clean energy, new emissions standards for cars and trucks. History may well reveal that Obama showed more personal courage on this issue than any other.

The Obama years have been a catastrophe for American freedom, perhaps a point of no return. In 2008 it was still possible to imagine that the power-grab of the Bush-Cheney era was reversible. Instead the president has consolidated and expanded the powers of secret government, while offering only token opposition, if that, to the Citizens United decision.

The Affordable Care Act’s progressivism stands out as the embodiment of Obama’s best intentions. Some 3 million poor people have gained access to health care thanks to the extension of Medicaid. But those people will not be in deep-southern states where poor people are numerous but Republicans rule. I see this convergence as a consequence of watermelon politics, as unsavory a legacy of Obama’s time as Obamacare is fine. – Nell Painter

It might very well be insurance exchanges, rather than the expansion of coverage, that stands as the most significant aspect of the Affordable Care Act. That is especially the case if the exchanges work and therefore lay the foundations for privatizing or ‘“marketizing” Medicare and Medicaid. As much as some called him a socialist, he might well be remembered as someone who de-socialized public health care. – Alexander Gourevitch

Obamacare is easily the signal accomplishment of this president, assuming current efforts to unravel it will be defeated. It’s an achievement that will put Obama in the ranks of FDR (Social Security) and LBJ (Medicare) because of its enduring impact on the average American’s well-being. He won’t need bridges and airports named after him since opponents already did him the favor of naming it “Obamacare.” – Thomas Holt

Even though Obama’s recent executive action on immigration has received a great deal of attention, it may have a greater long-term impact than the current political fracas. According to one poll, almost 90 percent of registered Latino voters support the measure. The number of Hispanics in the United States is projected to double by 2060, which means that one-third of the nation’s population will be Hispanic. Obama’s executive action may not only help stabilize the country’s Latino population but also cement much of its loyalty to the Democratic Party.

Obama’s establishment of the U.S. Cyber Command in 2009 will likely mark the moment that U.S. global-force projection began a historic shift from the Cold War’s heavy-metal military of aircraft carriers, strategic bombers, and tanks to an agile array via aerospace and cyberspace.

No question on this one: Obama will get much more credit as time passes for saving the U.S. and global economy from a major crash and launching a robust and sustained economic recovery. The question mark will remain how equitable the recovery proves to be.

Over the next 20 years, Obama’s standing will move from the top of the bottom third to the bottom of the top third of presidents.

Rahm Emanuel, had his hand in everything, not just Obamacare. He was the New Democrat attack dog who did the insider dirty work while Obama tried to rise above, or at least stand back from, the fray.

John Brennan, the figure with cardinal-like bearing and hidden influence, who consistently protected the CIA’s interests, both from his job on the National Security Council in the first term and as CIA director in the second.

Topic: How Will We Reconsider The Historic First?

Obama was and wasn’t a black president. It is hard to think of anything he actually did where the fact that he was black, rather than the fact that he was a moderate Democratic president, seemed to matter. If anything, the fact that he is black but was primarily a moderate American president will be seen as evidence for how much the institution makes the man, not the other way around. – Alexander Gourevitch Read the full questionnaire

One theme dominates American history from its origins to this morning’s news — the consequences, and how to deal with them, of the importation into the United States of Africans as slaves. President Barack Obama is not a descendant of slaves, but he is black, and that fact has unloosed or perhaps only illuminated a renewed white political resistance to racial equality that future historians will record as the third phase of the struggle by white Americans to retain political and social control. The first phase, centering on the question of slavery, extended from the counting of black slaves as three-fifths of a man in the Constitution of 1787 through ratification of the 13th Amendment banning slavery in 1865. The second phase, triggered by white shock at the social revolution implicit in the end of slavery, centered on white use of vigilante terror and control of the courts to deny political and civil rights for black Americans. Soon after the civil-rights acts of the 1960s ended the second phase, a third emerged, triggered by white shock at the fact of black legal and political equality. The first line of white defense in each phase has been denial—denial in the first phase that slavery was cruel, exploitive, and wrong, and denial in the second phase that lynching, Jim Crow laws, and whites-only primaries were intended to control African-Americans. In the third phase, it is denied that implacable Republican hostility to Obama has anything to do with race; that the all-Republican South, like the all-Democratic South which preceded it, is primarily an instrument of white control; that voter-ID laws are aimed at blocking votes by blacks and Hispanics, and that the predominance of white men voting Republican (64 percent in the midterm elections) is explained by race. History suggests that it takes roughly 50 years for denial to run its course; after that, everybody will know what the struggle is about, and no historian will blame it on Obama. – Thomas Powers Read the full questionnaire

The president’s blackness will matter a great deal, mainly because I think it shaped how many Americans viewed him and gave ammunition to his opposition. And on the other hand, I think Obama’s being black will influence the way that young people see the world. Having a black family living in the White House is important symbolically, as it suggests that the United States is not a “white” nation. – Annette Gordon-Reed Read the full questionnaire

To any historian with a long view, Obama’s election and (don’t forget) reelection will be seen as another sign of the declining significance of race over the past 50 years. No one sees that today. We’re constantly told that we need to “talk about race,” and then talk about talking about it. But the Obama years will be remembered as the period when class, and not race, became the great social cleavage in early-21st-century America. – Mark Lilla Read the full questionnaire

Obama is a living embodiment of American exceptionalism, of the capacity of any individual, in a free nation, to aspire to the zenith of success and achieve it by dint of hard work and ambition. He is everything Lincoln, FDR, and LBJ could have imagined as the prized harvest of the racial seeds they sowed. And yet biography is not history. A generation from now, historians will do a postmortem and pronounce the exceptional man an unremarkable leader on America’s most enduring challenge. They will dissect in a thousand ways with precision and compassion the promise and possibility that a single black body — truly African and American — could hold a nation together and suture its deepest wounds. Obama is the apotheosis of the assimilation society and the end of aspiration as the currency of racial change. He is the dreamer’s dream unrealized. America is redder and bluer, whiter and blacker, richer and poorer, more unregulated and less free. The rhetoric of a more perfect union as ballast through the storms of congressional obstructionism, state-sanctioned violence, voting restrictions, binge incarceration, and poverty not seen in more than half a century will have proved insufficient to right the ship of our racial state. He will have taught us that our leaders must lead knowing history is not a linear arc of progress from Seneca Falls to Selma to Stonewall. That the present can fall back into the past and that no man or woman’s singularity can bring us to shore alone. In these ways, he will have navigated us to our Third Reconstruction, better prepared to face the challenges before us. – Khalil Gibran Muhammad Read the full questionnaire

Obama’s blackness will matter largely as a continuing excuse for national self-congratulation, at least among the punditocracy. To historians, Obama’s being black may also help explain his timidity on policy matters, his willingness to conform to the Washington conventional wisdom. – Jackson Lears Read the full questionnaire

The GOP moves will be seen as the main way that race mattered in this period and will become a stinging source of regret and shame to almost all Americans, including to most future Republicans. – Theda Skocpol Read the full questionnaire

Obama catches hell because he represents black power even more than because he incarnates black power. – Edward Baptist Read the full questionnaire

The fact that he was the first black elected as president will always be the most astonishing thing about his presidency to most Americans of all races 20 years from now. And most interestingly, his name and his presidency will be used by those on both sides of that divide as proof of their argument as to whether we still have a long way to go or we’ve finally arrived. – Robert Williams Read the full questionnaire

The Most Successful Speech “A More Perfect Union,” Obama’s 2008 speech on race, overwhelmingly chosen as the most enduring of his presidency — even though it was given before he was elected: “I can no more disown [Reverend Jeremiah Wright] than I can disown the black community. I can no more disown him than I can my white grandmother — a woman who helped raise me, a woman who sacrificed again and again for me, a woman who loves me as much as she loves anything in this world, but a woman who once confessed her fear of black men who passed by her on the street, and who on more than one occasion has uttered racial or ethnic stereotypes that made me cringe. These people are a part of me. And they are a part of America, this country that I love.” — Excerpted from “A More Perfect Union,” 2008. The vast majority of respondents chose this speech on race as the most enduring of his presidency—even though it was given before he was elected. – Jackson Lears Read the full questionnaire “No American politician running for high office had said anything like that since the populist Tom Watson in the 1890s.”

How much did it matter that John F. Kennedy was Catholic? It mattered in the sense that after his election, being Catholic no longer constituted a barrier to the presidency. Yet JFK’s entry into the White House did not substantively affect the status of Catholics in the United States. Much the same is likely to be true with regard to African-Americans and Obama. – Andrew Bacevich Read the full questionnaire

I suspect that President Obama’s race will ultimately seem akin to President Kennedy’s religion. Each will certainly be remembered for their pioneering role, but upon closer inspection it’s clear that neither of them wanted to be remembered primarily (or even partially) for the breakthrough he embodied. On the campaign trail, each candidate understood that his unique background attracted many voters but threatened to alienate even more. Accordingly, each sought to avoid the issue until circumstances dictated that they confront it directly. When his opponents worried openly that he would take orders from the Vatican, Kennedy made a major speech in 1960 to assure panicked Protestants that he would show no religious favoritism. “I am not the Catholic candidate for president,” he insisted. “I am the Democratic Party’s candidate for president, who happens also to be Catholic.” Obama likewise downplayed race in 2008 until Jeremiah Wright forced his hand. He then delivered a similar speech, assuring white voters that he would not display any racial favoritism as president. Once in office, both presidents went to great lengths to prove those claims. Obama steered clear of anything that could be construed as “special treatment” for racial minorities, taking a lighter touch with issues of race relations than the previous two white occupants of the White House had. “I can’t pass laws that say I’m just helping black folks,” he said. “I’m the president of the United States.” Critics still see racial motivations in virtually everything he does. But as the contrast between the paranoia of such critics and the plainness of Obama’s actions becomes clear to Americans over time, the power of racism will be diminished – much as the power of religious bigotry was after Kennedy’s presidency. – Kevin Kruse Read the full questionnaire

The post-civil-rights racial order is coming undone on Obama’s watch. Thanks to affirmative action and the normalization of values of diversity within elite institutions, the country has more racial and gender inclusivity at the top than perhaps at any other time in its history. At the same time, a racially disparate criminal-punishment system will, under current trends, lock up one in three black men during the course of his lifetime. The contradiction Obama embodies—“one black man in the White House; 1 million black men in the big house”—has something to do with this. – Nikhil Singh Read the full questionnaire

If Obama’s presidency is remembered as the moment when America finally elected a black president and began, in the aftermath of his presidency, to face up to how much of the criticism he received while in the White House was racially motivated, then his election will appear to have been an early signal of a historic change. If, as seems much more likely in the wake of Ferguson, America continues to ignore the legacy and the present consequences of centuries of racism, and if the U.S. remains as deeply divided by race as it has been since the origin of slavery, then his election will appear an anomaly, a fluke made possible by the Great Recession. – James Kloppenberg Read the full questionnaire

Anyone who expected Obama to take strong positions on racial inequality was not paying attention to his speeches and writing well before he entered the White House, or his rhetoric on the campaign trail. Over his entire career, he has mostly avoided racial controversies unless circumstances forced him to do so. He has offered up uplifting bromides about racial reconciliation, but mostly asserted that discrimination and injustice are residual. Part of Obama’s blandness on race has to do with political calculation. Every time Obama mentions race, even in passing, it becomes national news. Critics on the right accuse him “playing the race card,” of “hating white people,” of being “divisive.” In the end, the fact that the United States elected a black president might have narrowed the possibilities for addressing ongoing racial inequalities in the United States. – Thomas Sugrue Read the full questionnaire

It’s not just that Obama is the first black head of state in the U.S. but the first one in Western society. I believe Tony Blair once commented, “I’m not sure this could happen in the U.K.,” and I think he was right. Slavery is clearly America’s spiritual holocaust — a collective trauma whose effects are still being worked out. No one can think back on the days of his European tours and first inauguration without realizing just how shocking and transformative his election was for American society. Does Lincoln’s Gettysburg Address still matter? His second inaugural? These were pivotal moments in American history, and so is Obama’s election. It can only happen once, and, as such, will never be forgotten. – Harry Stout Read the full questionnaire

Smart undergrads now being born will have to work to understand why we think Obama’s color has much to do with how we rate his accomplishments in office. – John McWhorter Read the full questionnaire