His last trip to chicago as president to say farewell to the nation. The soundtrack for our day . Music from the president s own spotify lists. Alabama arkansas i do love my ma and pa not the way that i do love you tonight, youre gonna talk to the American People. Is this a hard one . Do you know what youre going to say. I know what im going to say. I gotta make sure i get through it properly. You know, when you when you reflect back on eight years, for all the highs and the lows, the one thing that is a constant is the incredible dedication of the people who got you there and who helped you do your job. Everybody from the staff at the white house to the folks who make sure this airplane flies to supporters who would write me notes, you know, when things werent going well, to the people who would say that the work we did made a difference. So, i think that that sense of gratitude that i feel for those folks i just hope im able to express that. You have been a lot of places on this airplane. Yeah. Around over 400 missions. Right. Were told. Whats it like to be on here . This is the final flight. Or the final trip. Well, this is the final trip. We get our last flight after the inauguration. But this will be my final trip as president. You know look, its a nice plane. But, what it also does is it brings back a lot of memories about trips that were consequential. This speech youre giving a lot of president s have given their farewell speech, but often from washington. Right. Why come back to chicago . You know, we always have reminded ourselves every day that we were in the white house that we werent we werent here just for the pomp and the circumstances. We were doing the peoples business, and my own career in Public Service started in chicago. And thats where i learned the power of ordinary people coming together and bringing about change that would make a difference in their lives. Thank you, well see you on the ground. Reporter chicago, the city he loves, that clearly loves him back. In the freezing cold, people lined up before dawn for free tickets to his last speech. This is a historic moment. Its literally our last chance to see president barack obama speak. Were going to miss obama. Chicago loves you obama fired up. Ready to go. Reporter but before his public appearance, a much more private one. He brought us to his favorite chicago diner valois. My first apartment was a block away at 51st and blackstone and so i used to come here for breakfast. These guys didnt used to pay me a lot of attention at the time. Reporter now hes a big deal always. Good to see you. Howve you been . You doing good . How you doin boss . Absolutely. Thank you guys. Should i ask for the president ial discount when i come back . Well, about that, they cant afford discounts, but the food here is great the people are wonderful. And this is a real Gathering Place for folks all around the hyde park and all around the south side so all the years that i was organizing, you got good food, and it was cheap. And you fill yourself up. I didnt cook a lot back then. Do you cook now . I dont cook a lot now either, but there was a point in between when i was doing a little cooking. Reporter we sat down to talk been the news of the day, but about his reflections on the last eight years. Lets talk about the journey. It did begin in chicago. Im only gonna do this once in the interview, i promise. But i wanna i wanna show you something. You have, of course, seen it. It was grant park, the victory night. I want you to watch this. 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. I promise you, we as a people will get there. Yes, we can yes, we can yes, we can yes, we can yes, we can. Did you . Yes, we did. You did . Look, if you had told me at the beginning of my presidency the day after, in fact, me winning the presidency that eight years later the economy would be stabilized, we would have cut unemployment in half from its peak, that the stock market wouldve recovered, that incomes last year went up for everybody of every age group, every racial group, every demographic. If you told me that we provided 20 Million PeopleHealth Insurance that didnt have it before, that we had seen this explosion in clean energy and cut down our carbon emissions, that High School Graduation rates were up at an alltime high, i wouldve said, all right, we did okay. Reporter his vision of hope was cemented by the years he spent pounding the pavement and talking with people here in the windy city. Im curious now eight years later, did you draw on that Community Organizer in your presidency . All the time. So i was working with churches. Most of the folks were a lot older than me at the time. And i had to win over their trust. And two things i learned. One was that you have to develop a relationship, and you have to listen to people in order to understand what it is that motivates them and concerns them. And the second thing is that once you listen to peoples stories, it turns out that people who, on the surface, seem different actually have common hopes, common dreams, common aspirations. And if you can get them to see each other in that way, then potentially, you can get some things done. Kept you grounded as president to some extent . Always. Reporter and that was just the beginning of our extraordinary conversation covering eight years that made history but didnt always make the progress he promised. Can you remember a moment in which it just struck you that theyre gonna fight me at every turn . Oh, that happened early. Reporter an evening of hard questions. Didnt the recovery, uneven as it was, plant the seeds for the election of donald trump . Reporter and stirring reflections. You do get emotional at times. I do. All in all, this was a pretty shameful day for washington. My biggest disappointment as president. I think any of us African Americans in prominent roles feel this struggle, am i being black enough . Am i too black . You know what im talking about . Yeah. Reporter then its time, for true confessions my staff will tell you i can curse like a sailor behind closed doors sometimes. It sounds like youd like a do over . Well, no. Okay. First of all, my wife would leave me. Ah david, please, listen. Still not coughing. Not fair you guys waffles are my favorite ah some cough medicines only last 4 hours. But just one mucinex lasts 12 hours. Start the relief. Ditch the misery. Lets end this. Of being there for my sons winning shot. That was it for me. Thats why im quitting with nicorette. 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Im the son of a black man from kenya and a white woman from kansas, and for as long as i live, i will never forget that in no other country on earth is my story even possible. When the history books are written, in the first paragraph, if not the first sentence, its gonna say the first africanamerican president. There are so many expectations, as it turned out to what that meant. Did you wrestle with that . Did you how how did you articulate the expectations well that were thrust upon you . I think that its hard to generalize. I i i think the whole country took some pride, and it was legitimate, that we had traveled enough along our journey, from slavery and jim crow and discrimination, to the point where we could elect someone who looked like me to the highest office in the land. And elect me pretty handily. So, i think that pride is something that was a positive. I think it pointed to where we need to go. I think any talk of it being a Postracial America after my election was never realistic. I think it was but thats was a lot of that talk, though. Well, you know, i i think in fact that talk was not only naive, but i think created some problems down the road because two things happened. Number one, it meant that African Americans and other minority groups might have felt as if the problems that have built up over centuries, a wealth gap, an education gap, you know, significant poverty, that those things could be addressed overnight. On the other hand, among i think some you know, white voters, who sincerely were glad to see that the country had made this breakthrough, there was also made an unrealistic notion that somehow, okay, that means discriminations over. But is there a third group that just didnt want a black president . Well, undoubtedly so. Theres no doubt about that. But in the same way that you wouldnt expect in a four year span or an eight span to undo the entire legacy of race in america, social attitudes also dont transform in four years or eight years. They it happens over generations. And so sure, there is residual racial prejudice in this society. And i know you dont believe that were more divided racially. No. Today. I dont. And and and historically youre right. There are there are some historic markers that well, i think there are. [ chuckle ] would suggest otherwise. Pretty strong ones. Yeah. There are some pretty [ laugh ] strong ones. But but the but the fact is, i think a lot of people looked at you and said, this is the guy thats gonna make those arguments about inequality. Hes gonna use this platform. I think any of us African Americans who work in business or prominent roles, feel this struggle. Am i being black enough . Am i [ chuckle ] too black . Am i not black . You know what im talking about . I yeah. I i think every everybody wrestles with the fact that we are americans and we take great pride in this country that has given us so many blessings. And the fact that because of the color of our skin we are bound to a history that has often been cruel. You know, the struggle im talking about. And and and so the way i have always resolved this, and i talked to my daughters about this, is that my my starting point is not to assume the worst in others, but assume the best, to find those areas where it is possible to find common ground. And hopefully a generation that has been raised under my presidency will remember how ive talked about these issues in a way thats respectful of everybody. There was one moment that stood there was one moment that stood out to to a lot of people. It was the reverend pinckney funeral. Yeah. After the charleston massacre. You delivered the eulogy. And then you you went farther than talking about it. Im gonna read the quote. Maybe we now realize the way racial bias can infect us, even when we dont realize it, so that were guarding against not just racist slurs but were also guard ing against the subtle impulse to call johnny back for a job interview, but not jamal. Right. Jamal wasnt getting called back for that interview five years earlier. Why why did you not talk about things in in that explicit way before . Well, you know, the truth of the matter is is that one of the things you discover about the presidency is there are gonna be times where people will listen and times where they wont. There are gonna be times where youve got 15 issues and youve got to figure out what am i going to be investing the most effort and energy in . And where does it make more sense rather to use the bully pulpit to just do the work . This whole week, ive been reflecting on this idea of grace. [ applause ] the grace of the families who lost loved ones, the grace that reverend pinkney would preach about in his sermons. And this was a moment when i think the entire country recognized, not just the the the evil that had been perpetrated, but also this amazing response on the part of these people in this church who had seen friends and family gunned down. If we can find that grace anything is possible. If we can tap that grace everything can change, amazing grace. There were open hearts at that moment. And you were moved to sing amazing grace. Yeah. Amazing grace how sweet the sound you know, the interesting thing about the presidency is is there arent a lot of things that are spontaneous. A lot of things end up being scripted. By necessity, you have to be careful, because anything you say can move markets or start wars. I once was blind end up being the moments that are most meaningful. You felt pretty free at that moment . I mean were you on you know, you were yeah. A secondterm president. Well, i thought i i think i no. I i i think i just i was looking at the the two daughters of reverend pinckney who who were younger than malia and sasha, but wasnt that long ago, that they were in pigtails just like those girls that were sitting in the front row. May god continue to shed his grace on the United States of america. [ applause ] you have a good game face. You play it cool. But you also learned politics in illinois, in chicago. [ laughter ] do you have a vindictive streak politically . Ah start your day with 150 nourishing calories. In a bowl of special k. I love it eat special, feel special. Discover more ways to eat special. With special k. But so we dont have tormin wad to get clean. Charmin ultra soft gets you clean without the wasteful wadding. It has comfort cushions you can see that are softer. And more absorbent, and you can use up to 4 times less. Enjoy the go with charmin. 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There have been a couple of trends that occurred over the course of my presidency. First of all, i think the splintering of the media and the rise of social media means that a lot of people just have one source of information or a handful of places where they go to get the news. And it just reinforces whatever biases they already have. And thats true across the ideological spectrum. Everybodys got a louder platform. Everybodys got a louder platform. But they also dont have to Pay Attention to what people who disagree with them think. America just elected a man who is the polar opposite of you. I mean, if thats not divisive, i dont know what is. Well, but whats also true is that the majority of the American People, think ive done a good job. The majority of the American People think that the issues weve worked on have been the right ones. So so part of what we have to do is to figure out how do we get people back in a common conversation as opposed to these narrow, splintered conversations. Reporter the election in 2008 brought lofty expectations. It didnt take long for a harsher reality to set in. In 2009, a congressman interrupted the president s speech to a joint session. The reforms i am proposing would not apply to those who are here illegally. You lie. Reporter you lie. A stunning breach of protocol that foreshadowed a contentious eight years. I think this is beneath the dignity of the white house. Republicans in congress right now have shown over and over theyll do anything to rig the system for those at the top or to try to score political points on me, even if the obstruction keeps the system rigged against the middle class. We have suffered no shortage of words in the white house. What is missing is leadership in the white house. You had a tough time. You had a tough time getting what you wanted through. And you got a lot of it through. But was there a point can you remember a moment in which it just struck you that this isnt gonna be easy . Theyre going to fight me at every turn . Oh, that happened early. We we were in the middle of the worst economic crisis since the Great Depression shedding hundreds of thousands of jobs a month. And in the midst of that, we put forward a stimulus package, the recovery act, that ended up, most economists will acknowledge, working exactly the way we wanted it to. But i remember heading up to meet with the Republican Caucus to show them our plan and to solicit input and ideas from them. [ laughs ] and as i was driving up, my aide reads a statement from john boehner saying, we were were gonna oppose the president on this. We hadnt even had the conversation yet. [ laugh ] i was on my way to the meeting. How did you react to that . How did you react . Well, i i what it indicated was something that we kept on seeing throughout my presidency, and that was a tactical decision on the part of republicans to say