President Barack Obama on the campaign trail on behalf of Democratic presidential nominee Hillary Clinton, in Las Vegas, Oct. 23, 2016
Ethan Miller/Getty Images

It’s a tall task to assess the entirety of President Barack Obama’s two terms in office, to cull an ultimate judgment from all the success and missteps of his administration, and then measure that against the unprecedented obstructions it faced.

One can point to the decline in deficit and the growth of gross domestic product, or to the country’s continued economic expansion in step with a drop in unemployment rates. Or one can highlight the GOP’s refusal to cooperate with Obama as a means to invalidate his ameliorative policies and seek firm control of the House and Senate, or maybe discuss the devolution and fracturing of the Republican base, and the way in which that handicapped even those politicians on the other side of the aisle who wanted to compromise for the greater good. Or one could trumpet the Affordable Care Act as well as the shift in national attitudes and policy regarding gay marriage. One could also cast a somber retrospective glance at the controversial assassination of Osama bin Laden, the stain of drone strikes and ongoing infringements on individual civil liberties.

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In reflecting on Obama's presidency, you cannot get a feel for an era simply by rote recitation of objective fact. To get a sense of history, you need to engage in a perspectivism that distills a plethora of individual testimonials down to something that approximates truth. We tried that here.

I reached out to a wide swath of black Americans from across the socioeconomic spectrum and conducted interviews with around 30 of them, then chose the people who exhibited the most enthusiasm and thoughtfulness. They came from lower-class, middle-class and upper-middle-class backgrounds. They varied from businesspeople to entertainers, thinkers, academics, cartoonists, natural healers, writers and arts programmers. They hailed from all over the country, from Cleveland to Washington, D.C., from Atlanta to Texas, from Brooklyn, N.Y., to North Carolina, from St. Louis to Iowa.

I asked for their reflections on and insights into having had eight years of President Obama in office and a black first family in the White House—the political and psychological ramifications, the effect on race relations, the legacy of Obama’s two terms—and I made an effort not to lead anyone to any answers because what I really wanted was a natural range of opinions, thoughts and insights.

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In the aftermath, it has been provocative to sift through all of the reflections, which have underscored just how wide is the span of black identity and perspective, as well as some of the core commonalities regardless of that width.

I spoke with Dierdre Lockette, an accounting clerk and Beyoncé enthusiast; Bomani Jones, co-host of ESPN’s Highly Questionable and host of The Right Time With Bomani Jones; Randy Richards, cartoonist; De’Shawn Winslow, educator; Kecia Lynn, writer and editor; Shaka King, filmmaker (Newlyweeds, Mulignans); Raheem Dawodu, communications specialist; Monty Trice, former engineer and current businessman; Andre Perry, arts programmer and essayist; and Shanti Roundtree, writer, intellectual and natural healer.

 Obama’s Election in 2008

The Obamas on election night, 2008
Joe Raedle/Getty Images

How did he get into the White House? It seemed impossible. It made the inconceivable conceivable for a generation. We really believed we changed the world, and that there was more to come.

Bomani Jones:

I just couldn't grasp the idea America was going to elect a black president until the very end. How did he get into the White House? A black man can barely get into my condo building! So there was a real sense of optimism, albeit a qualified optimism. It's one thing for a segment of white America to dislike black people … but just maybe if you're so good at what you do, in spite of that contempt, people might be willing to vote for you—or on the more local scale, to support you regardless of your background or skin color, when you demonstrate talent and ability.

Kecia Lynn:

The narrative on which this country was founded—not “all men are created equal,” but “all white men are created equal, and everyone who isn’t a white man is a subject”—is so deep, and so many people, regardless of race, are invested in it, that when a black person arrives who not only does not fit the narrative but refuses to submit to it, they literally don’t know what to do about that person. It’s bad enough when we’re talking about Fortune 500 boardrooms, research laboratories and most Silicon Valley IT shops. Those are pretty rarefied spots for black people, certainly. The White House, though? That’s a whole new level of uppity.

Raheem Dawodu:

I grew up in a very black, working-class town in Prince George's County, [Md.,] and I had already voted in elections thanks to my Nigerian mom, who made it known I had to vote or die … literally. The morning I voted for Obama, I remember a line that looked to be a mile long. I’d been voting for six years and was able to get in and out of the polling station in five minutes. This day was different.

I watched the results at home with my family, and we all just hugged each other and shed tears. Not only a black man, but a son of Africa, was president of the United States. For the first time, we did it. My generation. We beat the established Democratic Party candidate, then we beat an established white male political institution in the general election. And we really believed we changed the world, and that there was more to come.

Dierdre Lockette:

I remembered being jarred by the racist dog whistles, and not just from Republicans. Bill and Hillary [Clinton] shocked me how they worked the racist wink and nod with the white middle-class. I was all in for sure then. Not just because he was black, but because Barack seemed more candid and honest about the challenges our country was facing. He made sure we knew it was going to take effort from everyone, and teamwork always draws me in.

Monty Trice:

I'm a pretty big 2Pac fan, and I always remember his line, "Although it seems heaven-sent, we ain’t ready to have a black president." I was 14 when he said that. I was taking gifted classes and well on my way to being the first person in my family to go to college. But even then, at that age, I felt like I'd never see a black president in my lifetime. It seemed impossible. Now America can be split into two eras for black folk: a time when a black president seemed like mere fantasy, and a time when it seemed as normal and American as apple pie. It made the inconceivable conceivable for a generation. For the future.

What a Black Man and His Family Occupying the White House Meant for Black Self-Esteem and Image

President Barack Obama, daughter Malia Obama, first lady Michelle Obama and daughter Sasha Obama walk to Air Force One at Castle Airport on June 19, 2016, in Merced County, Calif.
BRENDAN SMIALOWSKI/AFP/Getty Images

It exemplifies two things that have kept black people alive in this country all these many years: strength and faith. He expanded the very definitions of American blackness, not just from a white perspective but within the collective black conscious. America needed Barack to reinvigorate the idea and ideal of the American dream. This is who they say we aren't. That’s significant.

Randy Richards:

When I think of how Obama's presidency has affected black people, I think of the 106-year-old woman who danced with the Obamas. Consider the fact that she was born a good 60 years before the Civil Rights Act. To see someone that looks like you in the highest position of power in the world—especially considering all the things she must have experienced in her lifetime—had to be a huge psychological moment for her. Seeing a black family living in the White House and being a model example of how to carry themselves in the face of intense scrutiny meant a lot to so many of us.

Shanti Roundtree:

I hail from that U.N.-styled family with maternal immigrant roots stretching to Georgetown, Guyana, intertwined with a long paternal lineage rooted in the Deep Creek area of Chesapeake, Va., which means both sides of my family sport pictures of Obama on the wall. It was the first time I'd ever seen a president's picture given the same weight next to our class pictures, wedding photos, loved ones gone.

Kecia Lynn:

One of my favorite photos of President Barack Obama is of him in the center of a circle of black men with their heads bowed in prayer. I believe the men were all pastors; I’m not sure. I’m not sure whether the photo was taken early in his presidency or later, but I like to think it was taken earlier, if for no other reason than it exemplifies two things that have kept black people alive in this country all these many years: strength and faith. I envision the Obamas wrapped in a powerful circle of ceaseless prayer, one that’s maintained by people from all over the world, but especially by black Americans, who knew, almost as well as the Obamas themselves did, what they were getting into by applying for, and then accepting, the job of first family.

Andre Perry:

I'd just finished my MFA in 2008, so I'd been in my head a lot: thinking about my place in the world; contemplating the complexities of identity. Having Obama as a model of public service has certainly helped with the evolution of my idea of self. He has been a backdrop for my own journey, my own development. He expanded the very definitions of American blackness, not just from a white perspective but within the collective black conscious.

Bomani Jones:

Obama was a sort of mirror for other black people like him who have been trying to navigate their own blackness in a predominantly white society, and eventually concluding there is no level of respectability that will save them. Mixed race, upper class, educated, etc. Though on one hand, he normalized many things identified with blackness—whether correctly or incorrectly in public opinion—he further exotified other things by sneaking them in the back door, the "Love and Happiness” concert/house party thrown in conjunction with BET being the most recent example.

Kecia Lynn:

The image is important for other people more than for us. There are a lot of black men like Obama. There are a lot of black women like Mrs. Obama. There are a lot of black families like the Obamas. They’re really not special!

Shanti Roundtree:

Education is a DNA-ingrained expectation, so Occidental, Columbia and Harvard did not make him any less ours. For us, he was us, is us and is what we could aspire to be: respected, representative and at the helm. Ohhh, we talked about him, too, but always safely in private, where family business belongs.

Bomani Jones:

I feel a little removed from the impact of their image as a “respectable family.” I came from an idyllic nuclear family structure, so that image was old hat to me. That being said, when I talked to Ta-Nehisi Coates about the subject, he was adamant in affirming, the symbol of a so-called traditional black family does matter. The Obama family takes the norm and turns it on its head, counteracts fictions of pathology in the brightest spotlight. This is who they say we aren't. That’s significant.

Dierdre Lockette:

That beautiful family, though! Those baby girls and Michelle spoke to me on a deeper level. Barack was surrounded and supported by magical black women and girls and it reminded me so much of my family. Smart, beautiful and well educated—but you could see that Chi-town South Side, so I knew the Obamas were my family, too.

Raheem Dawodu:

Watching this young, beautiful black family … the symbol was not lost on anyone. This was a black family that debunked all we were told we could not do in this country. It is incredible to see Michelle Obama, who was once seen negatively by many Americans, now blossom into one of the most popular and beloved people in America. Even Donald Trump won't say a bad word about her, and he says bad things about everyone.

Shaka King:

It's not just that he was a black president. He was a young, attractive black president. In terms of societal codes, he has nimbly been black when he needs to, and white when he needs to. And it was important his wife be black and bold and beautiful. The image of Barack mattered to America, in general, as much to black Americans, specifically. In 2008 the country was incredibly unpopular overseas after Bush’s tenure. America needed Barack to reinvigorate the idea and ideal of the American dream.

Whether the Symbolism and Reality of a Black President Advanced or Strained Race Relations in America

President Barack Obama on the South Lawn of the White House on Oct. 25, 2016
Andrew Harrer-Pool/Getty Images

The man alone neither improved nor inflamed race relations. Obama didn't expose racism; his presidency happened and overlapped with the expansion of social media and clarified the pervasiveness of racism.

Andre Perry:

Like everything, it's very complex. There has been societal progression moving hand-in-hand with regression. Obama came to power in the age of social media, which has amplified the voices and opinions of people we normally wouldn't hear from in the past. That amplification of discontent would've been true for any one, but is doubly true from Obama as a black president. And the amount of visible violence against black people has heightened our sensitivities, and that has meant he has overseen a particularly tumultuous time. Circumstances—this amplification of voices, the plethora of footage of police brutality—might make tensions seem more extreme than they are.

Randy Richards:

I don't think Barack being in office made race relations worse so much as it made prejudices a lot more overt. A certain segment of the population went a little crazy. You saw it with Donald Trump's Birther campaign, with Newt Gingrich calling Obama the food stamp president, all the obstructions he's had to face from Congress.

Kecia Lynn:

Recently I saw a list of all the things Trump has said or done since he announced his intention of running for president. If Obama had said or done even one of those things in 2008, he would have been knocked clean off the political stage. There’s a double standard that’s so obvious that people don’t even try to argue against it anymore … sensible, clear-headed, race-aware people, that is. Are there more of those now? Maybe. If so, we certainly have the first family to thank for it.

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Look at where we’re at right now with this election cycle. The Obamas are a normal family, yet they tried to make them seem as abnormal as possible. Trump is the most abnormal presidential candidate in American history, and yet they have done a really good job trying to make him seem normal. What else is this but evidence of a profoundly unhealthy and illogical attachment to a narrative that flies in the face of progress?

De’Shawn Winslow:

In a way that I never had before, I soon became more aware of my being a black person and a black man. I began to feel that my blackness, and my black maleness, was often under scrutiny. Everything I said and wrote was scrutinized, I felt, in a way that it had never been before. Every man I dated, every person I befriended, every place I sought employment was scrutinized. A new scrutiny. A "We have a black president now" scrutiny. The scrutiny came in the form of "friendly" conversation, and it came from blacks and whites.

Shanti Roundtree:

The man alone neither improves nor inflames race relations. The Man, in fact, was played by James Earl Jones 36 years before reality ensued. Rod Serling wrote the screenplay. But I'd say his presidency conjoined with technological advancement and accessibility to illuminate race relations, which have never been great. They'd just been going largely unbroadcast.

Bomani Jones:

Look at the places and institutions that mark Obama: Kansas, Hawaii, Harvard. This was an “acceptable” black man. You can be an acceptable black man, and even become the president of the United States, and still get the black man treatment. In other words, someone on the wrong side of the race equation can get to the highest office yet deal with the same nonsense of skepticism, persecution and stigmatism. For the first time, a black person was legitimately the topic of discussion for everyone in America. So the conversation was louder than usual, more public, more widespread.

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Barack didn't expose racism; his presidency happened, overlapped with, the expansion of social media and clarified the pervasiveness of racism. Ostensibly reputable people used extreme and antiquated language to assess him. When you saw the fiction behind those criticisms, it became undeniable these people feared the notion of Obama rather than any of his words, actions or policies.

Shaka King:

The opposition to the notion of Obama clarified for me the president as symbol. And not just that he symbolized a shift that made so many white people anxious. But for the first time in my life, I was forced to reckon with the office of the president as being largely symbolic to all of us.

Obama’s Legacy

President Barack Obama cradles a baby during a visit to the Charcoal Pit restaurant in Wilmington, Del., on July 17, 2014.
JEWEL SAMAD/AFP/Getty Images

Given the circumstances, what he's accomplished is almost a miracle. He was the most measured and reasonable president I've seen. But the office has built-in limitations. Some are measured by mile markers, while others need only pass the slide-rule testHe probably edges Bill Clinton as the best president of my lifetime. They are, after all, family.

Monty Trice:

Fast-forward eight years, and the allure of the first black president has worn off for most folks. For me, however, Obama being in office is still as important as the first day he stepped foot in the White House. It happened. The first black president. Not only did it happen, it happened for eight years, and he never embarrassed himself or us. That fact should not be taken lightly. I have two nephews and a niece who have only known a black family in the White House throughout their lives. Countless white people, here and abroad, have been exposed to a smart, charismatic black man who is a great father and husband. That image is powerful in a world of stereotypes.

Shanti Roundtree:

I suspect President Obama's tenure is majorly responsible for germinating new seeds of thought in popular media. Our president will retire in January 2017 as the movie Southside With You hits Netflix. When Obama began, aside from a scad of Tyler Perry movies, I noted a steady uptick in dramatic mainstream movies featuring us, including films like Precious, The Help, 12 Years a Slave, Mandela: Long Walk to Freedom, Fruitvale Station, The Butler and 42, among others. And breaking the color barrier hasn't been the only parallel made between Jackie Robinson and Barack Obama. Each IMDb blurb is silently inviting us, and America, to acknowledge how far we as a nation have come. and how far we have to go.

Shaka King:

Without question, on the subconscious level, the leader of the United States being a black man has had an empathizing effect on television programming. Instagram, Facebook and Twitter have galvanized that sort of empathy; people are interacting so much more. The exact extent of that effect is difficult to quantify. Empire's ratings being so high has played just as big a role—what moves the needle in Hollywood is money. The state of blacks in motion pictures is still tragic, borderline Jim Crow era.

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I'm speaking in a bit of hyperbole, sure. But there's an archaic model still at work in studios as far as what kind of movies are being made and how those films are being marketed and promoted. Television, on the other hand, is broadening. You couldn't have a show like Donald Glover’s Atlanta until this year. Atlanta's the first zany black show, outside of sketch comedy, on a network. Ever. Think about that.

Dierdre Lockette:

I’m from St. Louis and lived near Ferguson [Mo.] and have had personal experience with police misbehavior and abuse. So I expected something more from Obama after Michael Brown. Some concrete policies. Making sure they were passing out police cameras the same way they passed out tanks and assault weapons. Some kind of universal standard all police departments had to meet. I wanted him to strong-arm these cops like they had been strong-arming us all these years, and none of that happened.

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I'm still not over that disappointment. But I have to temper it all with something an ex used to say to me. After some promise unfulfilled, he would tell me, "Baby, I'm doing the best I can and that's all I can do." It wasn't enough, but in between those lines, he was saying he was doing the best he could in this society that didn't want to see him succeed at anything. And that's Obama’s predicament to me. I sincerely believe he did the best he could. Given the circumstances, what he's accomplished [is] almost a miracle.

And I'm forever inspired by the black girl magic that is Michelle and those beautiful girls. They all were at war for these eight years, and despite their battle scars, they've continued to rise. Our country is in a much better place than eight years ago, Overall, I'm inspired. I am definitely heartbroken to see them go and forever grateful for their example.

Raheem Dawodu:

Eight years later, and I do not believe the President Obama presidency has ever come close to the moment of when he was elected president. He never could because it’s unrealistic. I have aged eight years since then, and I have changed my thinking a lot since that night. I realized that there is no way any American president can ever truly do much to uplift African Americans, or any oppressed group. It is just not the nature of that position. The best president ever—and I think President Obama will be seen as that many years down the line—cannot be anything more than C-minus to oppressed persons and the impoverished.

Andre Perry:

He was the most measured and reasonable president I've seen. But the office has built-in limitations. It made him complicit in murder, drone killings. Yet he has sought peace internationally. Within the constrictions of the office, he has been progressive. He has given deep thought to what the future of the world looks like, and you have to believe he wants the very best for this country. He has pushed a lot of forward-facing policies. They might not be ideal, but they represent a significant step in the right direction.

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A lot of his legacy hinges on the next four to eight years. We are rooted in the now, and we can't tell the future. You exist in realities that are in discordance with each other when you are American. Obama's election can be viewed as good, while police brutality can be viewed as a sign of residual racism—but the two don't necessarily move in lockstep.

You know what’s woefully untold as a story? The mistakes Andrew Johnson made as a president in the wake of Lincoln’s assassination. We’re still paying the cost for the poor job Johnson did reconstructing the nation. Obama can’t counterbalance over a century of missteps in eight years; nor should we have expected him to. Things can be revamped on a local and state level, and individuals have to be vigilant in fighting for progress. We play such an important role in building the communities that elect better leaders, and we forget that and instead look to the figureheads. There can be no face of the movement without the movement.

Shanti Roundtree:

I haven't seen more equity, power or wealth accorded to our communities. I still see hordes of our greatest treasures lost to circumstance: incarceration, lack of alternatives, fear of success and debt. But on an individual level, Obama’s legacy for me is excellence and grace. Sadly, proof positive that different standards are still very much a thing, and some are measured by mile markers while others need only pass the slide-rule test.

Bomani Jones:

In 20 years, it'll be fun to tease out who he was as opposed to what he means to us, now. The summer of 2008 was as fearful a time as one can imagine. Dreams and livelihoods went up in smoke. So yes, Obama's tenure has been a success. It has been laid bare for America that a lot of the things we imagined we were beyond, we are nowhere near conquering. Here’s an interesting question: If we don't collectively observe all the things that happened to Obama and during his tenure, do we get a Colin Kaepernick? Does he still have the confidence to take his stance?

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If there's anything I've learned in the last eight years of Obama, it was the need to reconcile my personal belief of what I want a president to do with the narrow constrictions of the job. By clarifying the limitations of the office, his two terms also emphasized the need for us as individuals to take action against societal ills like police brutality. I have a nuanced view of Obama as I've ever had of any president in history because I was forced to really reflect on his job. Which has allowed me to come away with a complete portrait of the man. He provoked an entire nation to revisit its notions of what does it means to be black, to be educated, to be intellectual, to be president. And given the tumult he presided over, he probably edges Bill Clinton as the best president of my lifetime.

Kecia Lynn:

Like most black Americans, and like most progressives in this country and around the world, I am grateful to have lived to see a black family occupy the White House. I am grateful that my nieces have only ever known a black president. I am beyond grateful that my parents and the rest of the elders, the ones who remember what life was like before this president was born, lived to see it happen. I imagine them praying for the Obamas at night. They are, after all, family.

Also in the His Lasting Legacy series on The Root:

‘I Wanted to Be a Part of History’: What It Means to Work for the 1st Black President

Historic Presidency, Historic Opposition: The Legacy of President Barack Obama

Fighting Racism in the Age of Obama

Obama’s Battle for Black Boys: My Brother’s Keeper 2 Years Later

Obama Legacy: A First Lady Like No Other

Affordable Care Act Remains a Defining Moment in Obama’s Presidency

Scold-in-Chief? The Love-Hate Relationship Between HBCUs and President Obama

‘1st Gay President’? No. But Is Barack Obama an LGBT Ally? A Resounding Yes

Underestimated on Foreign Policy, Obama Has Left Opponents ‘Sucking Wind’

Obama and the Congressional Black Caucus: Allies and Foes

T.D. Williams was born and raised in New York City, where he spent his youth in a welfare hotel for the homeless in Times Square. He has been a soda salesperson, camp counselor, a parking lot attendant, a waiter, a bartender, a civil rights activist, a dean of college admissions and an adjunct professor. He is currently finishing his first novel, and his writing on sports and societal issues has appeared in various publications, including Sports Illustrated. Follow him on Twitter.