brakes are getting warm. confirmed, daniel you need to cool your brakes. understood, brake bias back 2 clicks. giving them the agility to have speed & precision. because no one knows & like at&t. we have never been just a collection of individuals or a collection ofed states or blue states. we are and always will be the united states of america. 2008, grant park, chicago. the night that barack obama was elected president. >> yes, we can! yes, we can! yes, we can! ♪ ♪ now, eight years later,

president obama is going home. ♪ >> we joined him on air force one for 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. ♪ ♪ ♪ >> tonight you're going to talk to the american people. >> right. >> is this a hard one? do you know what you're going to say? >> i know what i'm going to say. i have to make sure i get through it properly. you know, when you reflect back on eight years, for all of 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 the airplane flies to

supporters who would write me notes when things weren't 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 i'm able to express that. >> you have flown places on this airplane, over 400 missions, we are told. >> right. >> what's it like to be on the final flight, or the final trip. >> the final trip. we get the last flight after the inaugurati inauguration, but this will be my final trip as president. look, it's a nice plane, but what it also does is it brings back a lot of memories about trips that were consequential. >> this speech, a lot of presidents have given their farewell speech, but often from washington, why come back to chicago? >> we always have reminded

ourselves every day that we were inhe white house that we weren't -- we weren't here just for the pomp and the circumstances. we were doing the people's business, and my own career in public service started in chicago, and that's where i learned the power of ordinary people coming together and bringing about changes that would make a difference in their lives. >> thank you. we'll see you on the ground. ♪ ♪ ♪ >> 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. it's literally our last chance to see president barack obama speak. >> we're going to miss obama. chicago loves you.

>> obama! ready to go! >> but before his public appearance, a much more private one, he brought us to his favorite chicago diner maloy's. >> my first apartment was a block away at 51st and blackstone. i used to come here for breakfast. these guys didn't pay a lot of attention to me, at the time. >> good to see you. how have you been? >> i should ask for the presidential discount when i come? >> i don't know about that, they can't afford discount, but the food here is great and the people are wderful and this is a real gathering place for folks all around hyde park and all around the south side so of all of the years i was organizing we got good food and it was cheap. and i didn't cook a lot back then. >> you cook now? >> i didn't cook a lot now either. there was a point in between

when i was doing a lot of cooking. >> testing, one, two, three. >> sat down to talk about, not about the news of the day, but about his reflections on the last eight years. >> let's talk about the journey. it did begin in chicago. i'm only going to do this once in the interview, i promise, but i want to show you something, and it was grant park. >> the road ahead will be long, the climb is 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. >> 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 would have recovered, that incomes last year went up for everybody of every age group, every racial group, every demographic. if you'd told me that we'd provided 20 million people health insurance that didn't have it before, that we've seen this explosion in clean energy and cut down our carbon emissions, that high school graduation rates were up at an all-time high. i would have said we did okay. >> his vision of home was cemented by the years he spent pounding the pavement and talking with people here in the windy city. >> i'm 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 people's stories it turns out that people who on the surface seem different actually have common hopes, common dreams and 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. >> and that was just the beginning of our extraordinary conversation covering eight years that made history, but didn't always make the progress he promised. >> can you remember a moment in which it just struck you that they're going to fight me at every turn. >> well, that happened early. >> an evening of hard questions. >> didn't the recovery, uneach as it was, plant the seeds for the election of donald trump? >> and stirring reflections.

>> you do get emotional at times. >> i do. all in all, this is 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. do you know what i'm talking about? >> i know. >> my staff can tell you i can curse like a sailor behind closed doors sometimes. >> sounds like you'd like a do-over. >> well, no. first of all, my wife would leave me. ♪ ♪

i'm the son of a black man from kenya and a white woman from kansas, and so as long as i live i will never forget that in no other country on earth is my story even possible. ♪ ♪ >> when the historybooks are written in the first sentence it will say the first african-american president. >> yeah. >> there are so many expectations, as it turned out to what that meant. did you wrestle with that? how would you articulate the expectations that were thrust upon you? >> i think that it's hard to generalize. 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 that looked like me to the highest office in the land. ♪ at last my love has come along ♪ ♪ >> 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 being a post-racial america after my election was never realistic. i think it was -- >> there was a lot of that talk, though. >> 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 had built up over centuries, a wealth gap, an education gap and significant poverty that those things could be addressed overnight. on the other hand, among some white voters who sincerely were glad to see that the country had made this breakthrough there was also man an unrealistic notion that somehow, okay, discrimination is over. >> is there a third group that just didn't want a black president? >> undoubtedly so. no doubt about that, but in the same way that you wouldn't expect in a four-year span or an eight-year span to undo the entire legacy of race in america.

latitudes don't transform in four years or eight years. it happens over generations and so, sure, there is residual racial prejudice in this society. >> i know you don't believe that we're more divided racially today. >> no. >> historically, you're right, there are historic markers -- >> some pretty strong ones. >> yeah, there are some pretty strong ones. the fact is i think a lot of people looked at you and said this is the guy that will make the arguments about inequality and he's going to 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 too black? you know what i'm talking about? >> i think 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 i'm talking about. >> and so the way i have always resolved this, and i talk to my daughters about this is that my starting point is not to assume the worst in other, 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 i've talked about these issues in a way that's respectful of everybody. ♪ ♪ ♪ world, keep on turning ♪ ♪ >> there was one moment that stood out to a lot of people, it was the reverend pinckney

funeral after the massacre and you went fatherer in talking about him, and i'll read the quote, maybe we now know the way racial bias can affect us so we're guarding not just against racial slurs -- >> and we're calling johnny back, but not jamal. >> jamal wasn't getting called back for that interview five years ago. why weren't you talking about that in that explicit way before? >> the truth of the matter is there are going to be times when people will listen and times where they won't. there will be times where you get 15 issues and you have to figure out what am i going to be investing the most effort and energy in and where does it make more sense rather than use the bully pulpit and just do the work. >> this whole week i've been reflecting on this idea of

grace. the grace of the families who lost loved ones, the grace that reverend pinckney would preach about in his sermons. >> this was a moment when i think the entire country recognized not just 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 weigh can fiwe can find t grace, anything is possible. if we can tap that grace anything can change. can find t anything is possible. if we can tap that grace anything can change. amazing grace. >> there were open hearts at that moment. >> and you were moved to sing "amazing grace." ♪ amazing grace, how sweet the

sound ♪ >> the interesting thing about the presidency is there aren't 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. ♪ >> but you do look for moments of human connection and in some ways those end up being the moments that are the most meaningful. >> did you feel pretty free at that moment? you were second-term president. >> i think -- no. i think i was looking at the two daughters of reverend pinckney

who were younger than malia and sasha, but it wasn't that long ago when they were in pigtails just like those girls. they were sitting in the front row. >> may god continue to shed his grace on the united states of america. ♪ ♪ you have a good game face. you play it cool, but you also learned politics in illinois, in chicago. do you have a vindictive streak? >> uh -- i'm so frustrated. i just want to find a used car without getting ripped off. you could start your search at the all-new carfax.com that might help. show me the carfax. now the car you want and the history you need are easy to find. show me used trucks with one owner. pretty cool. [laughs] ah... ahem... show me the carfax. start your used car search and get free carfax reports

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ask your doctor about lyrica. ♪ ♪ we can't move forward if all we do is tear each other down, and the political incentives as they are today too often rewards that kind of behavior. that's what gets attention. we can insist as lincoln did, that we are not enemy, but friends. >> the notion is that this is a more divided country today than it was when you took office. that may or may not be because of you, but many people accept that as fact, do you? >> what has happened is there

have been a couple of trends that occurred during 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 news, and it just reenforces whatever biases they already have, and that's true across the ideological -- >> everybody's got a louder platform. >> everybody's got a louder platform, but they also don't have to pay attention to what people who disagree with them think. >> americans just lelected a ma who is the polar opposite of you. if that's not divisive, i don't know what is. >> what's also true is that the majority of the american people think i've done a good job. the majority of the american people think the issues we've worked on have been the right ones. 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. >> the election in 2008 brought lofty expectations. >> so help you god? >> so help me god. congratulations, mr. president. >> it didn't 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! >> 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 they'll 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. was there a point, can you remember a moment when it struck you this isn't going to be easy? they'll fight me at every turn. >> that happened early. we were in the midst of the worst economic crisis since the great depression, shedding jobs in the month and we put in the recovery act that ended up, most economists will acknowledge, woing 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, and as i was driving up my aide reads a statement from john boehner saying we're going to oppose the president on this.

we hadn't even had the conversation yet. i was on my way to the meeting. >> how did you react? >> well, 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 no because their view was because if they said "yes" and if there was any bipartisan cooperation that that would benefit me politically, and if there wasn't that would hurt me politically particularly at a time when the economy was doing poorly. we could do well in the midterms if it seems washington is dysfunctional at a time when everybody is hurting. >> republicans did do well in the midterms and beyond and eventually taking control of congress and a week from now, the white house. >> didn't the recovery, uneven as it was that the people on the bottom were slower to recover than the people in the top, didn't that in some ways plant the seeds for the election of

donald trump? >> well, what is true is that the -- the ability of republican leaders to rile up their base helped along by folks like rush limbaugh and some commentators on fox news, i think, created an environment in which republican voters would punish republicans from cooperating with me. that hothouse of back and forth argument and sharp partisanship, i think, has been harmful to the country. >> you have a good game face. you play it cool, but you also learned politics in illinois, in chicago. do you have a vindictive streak politically? >> i tell you, my staff and my wife will tell you that that what you see is sort of what you get with me. i tend to be somebody who focuses on what it is that i want to get done as opposed to

focusing on whatever grudges have developed. now, look, my staff will tell you i can curse like a sailor behind closed doors times. there have been a bunch of times when i've been aggravated, but i tend not to personalize politics that much partly because of what i just described. a lot of the republicans, not just early in my presidency, but to this day are decent people who are responding to pressures that they're feeling. in some case there are some sincere differences on tough issues like abortion where i don't question the fact that they sincerely have a different view on these issues. so what i try to do is i try to get into their mindset and that, i think, dissipates the anger

that i have been some time been known to express. i went back and looked at this and forgot how heavy it was. you're standing in the rose garden, it's 2013. >> all in all, this was a pretty shameful day for washington. >> my biggest disappointment as president. ♪ everything your family touches sticks with them. make sure the germs they bring home don't stick around.

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somehow this has become routine. the reporting is routine. my response here ends up being routine. the conversation in the aftermath of it, we've become numb to this. ♪ >> you do get emotional at times. >> i do. >> he gets emotional about one issue perhaps more than any other, gun violence. >> every time i think about those kids it gets me mad, and by the way, it happens on the streets of chicago every day. >> my worst day as president was hearing that 20 6-year-olds had been shot in the most brutal way, in their school where they should have been safe, and it was only two days later where i had to try to comfort parents of

these 6-year-olds and their siblings, 10-year-old, 8-year-olds whose both sisters and little brothers have been aughtered. >> i can only hope that it helps for you to know that you're not alone in your grief, that our world, too, has been torn apart, that all across this land of ours we have wept with you. we've pulled our children tight. >> that day that i spoke at the sandy hook memorial is the only day i've seen a member of the secret service cry while they were standing there because every time i read out a name of one who had been killed the families, you could just hear the pain. >> charlotte, daniel, olivia,

josephine, anna, dillen -- >> i thought that, okay, this has to be a catalyst for some action by congress. i didn't expect that you'd see some huge movement on gun safety legislation, but i thought, well, they're going to have to make some effort and the fact that it didn't even get the kind of hearing and votes that you would have expected, it didn't generate a debate. that you actually had bipartisan legislation that had been sponsored atidn't matter. >> i went back and lood at this and forgot how heavy it was. you're standing in the rose garden, it's 2013. the senate has just failed to expand background checks for gun

sales and you're standing there with the sandy hook families. >> my biggest disappointment as president. >> i've heard folks say that having the families of victims lobby for this legislation was somehow misplaced, a prop, somebody called them. are they serious? do we really think that thousands of families whose lives have been shattered by gun violence don't have a right to weigh in on this issue? all in all, this was a pretty shameful day for washington. >> nine out of ten americans were with you on that. >> they were. >> and you couldn't get it done. did that tell you as powerful as this job is, the limits of your power? >> yeah. i taught constitutional law right down the street at the university of chicago. >> you're living it. >> the founders deliberately set up a system that separates powers, and distributes power, and not just among the different branches and different levels of government, and there's wisdom in that in the sense that the

likelihood of any single person doing real damage to the country is reduced. on the other hand, when basic civility and compromise breaks down that the system can get really stuck and what we've witnessed over the last six yearshe i lost the majority of theenate and the house is it's been difficult, not impossible, but exceedingly difficult to try to move legislation even when we had strong support from the majority of the american people. >> after failing to move a needle on gun safety for years, the president went around congress last january announcing a series of executive measures. >> our unalienable right to life, liberty and the pursuit of happiness those rights were stripped from college kids in blacksburg and santa barbara and

from high schoolers at columbine, and from first graders in newtown. first graders, and from every family who never imagined that their loved one would be taken from our lives by a bullet from a gun. >> watching those results, when you realized that donald trump was going to win, was there an unvarnished barack obama at that moment? ♪ ♪

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surprise. you know, generally speaking, not just me, but my team have been pretty good at seeing something coming, and you know pa are thely because the polling was so off and the data was off, was there a surprise. i think the president-elect would be the first to acknowledge he didn't run a conventional campaign. it's not clear that he or his team thought they were going to win. so i think more than anything it was just surprise, and there was a sense of disappointment that's inevitable when you've investeded a lot of time and energy into somebody who i thought would be a terrific president, hillary clinton, into a democratic party that i think had the right ideas. >> everybody is sad when their side loses an election, but the day after we have to remember that we're actually all on one

team. >> and, look, it did speak to a problem that we saw during the course of my presidency which was i had trouble transferring my personal popularity or support to the broader cause of th democratic party, and i think that's a legitimate criticism. i've thought about some of the things that you could have done. >> you were personally wounded by the result? >> yeah. some of what has happened in terms of losses in congress and the gubernatorial and state levels were just a matter of bad luck. in 2010 we were going to lose seats because i was the president in charge when people were terrified about what was happening to their economy and rightfully so, but that also ended up to be a gerrymandering

year and that's when the lines were drawn. it locked in a republican advantage for a number of years, but some of it is also that despite my organizing back ground, despite the grassroots nature of my campaigns, it was difficult for me to both do the work of managing an economy or foreign policy and dealing with terrorism and building the grassroots party apparatus that i think ultimately makes democracy work. >> it sounds like you'd like a do-over. >> well, no. first of all, my wife would leave me. >> wieldn't want that. >> and second of all, i think that every president looks back and says "i wish i could have cloned myself and done 15 other

things." you do the best you can. here's what i can say with great confidence and i think anybody that worked with me can cfirm it and certainly michelle and my girls can confirm it. i never got weary. every day i woke up and i worked really hard. >> but hard work didn't stop intense condemnation especially on foreign policy. with the spiral of war in iria, the controversial iran nuclear deal and russia's annexation of crimea, critics accuse him of i don't mean boldening russian president vladimir putin. >> you and i grew up in an era that america was the super power and an implied threat that if you mess with us we'll put that military to work. you were leched president on a mandate of we're tired of war. we have two wars doing and we don't want to do it anymore. putin begins toplex his muscle in ukraine and crimea.

did you give him the space to do that based on your reluctance, to engage, did he take that as an opening? >> no. this is an interpretation that i think is common in washington that the thinking is somehow the only exercise about power is military and the mythology that somehow we've been able to do whatever we want around the world in previous years, that's actually not been the case. america is by far, the most powerful military and it is by far the best respected country now. it wasn't when i came into office, but it's not as if russia today has greater territorial scope or relatively greater power than we do. >> however, he says russia and others pose a growing threat on the new battlefield, cyberspace.

>> i will tell you that the cyber issue is a different kettle of fish. i think we are moving into an arena now in which the ability at a fairly low cost for not just state actors like russia or china but also non-state actors to penetrate core functions in our society whether it's infrastructure, our financial systems, government and health records, that is moving faster than our defenses are moving and this is something that i've been aware of since i started. >> are we outmatched on that level? >> we're still -- we're pretty good at doing it if we have to, but we abide by certain norms and rules. our problem is we're more vulnerable because we are more digitalized than other countries are. we have more at stake if we get

into a full cyber war and what is also true is the cyberworld we occupy is not just government, it's every bank and every store and every business around t country. >> are you going to use, mail when you leave the white house? knowing what you know? >> well, you know what? my general rule about email is don't send something that you don't mind being published in the newspapers. >> yes, we can! yes, we can! >> did you see some idealism in that young man? >> i did, and that idealism hasn't left. i'm grayer. people like to note the additional wrinkles. ♪ ♪ what are you doing? getting your quarter back. fountains don't earn interest, david. you know i work at ally. i was being romantic. you know what i find romantic? a robust annual percentage yield that's what i find romantic. this is literally throwing your money away.

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that faith that i placed all those years ago not far from here in the power of ordinary americans to bring about change, that faith has been rewarded in ways i could not have possibly imagined. ♪ ♪ >> i worked really hard on the things that the american people cared about, and on the things that are most important for our future, and i've used this analogy before. you've ryou run your leg of the race, you get the baton and

hopfully you've advanced a leader and closed the gap when you pass the baton to the next person, and what i can say is eight years after i got elected the country is a lot better off by almost every measure and it's -- that's not a matter of opinion. people can ultimately make judgments about, o could he have donemore? this didn't get done. that didn't get done. we didn't solve racism in america. the middle east is still in chaos, but what i can say, and i think would be hard to dispute is that across the spectrum, america's stronger, more prosperous, more respected than it was before i started. >> will your legacy be measured in some way on the success or lack of success of the trump administration? will we have to look at you a couple of cycles beyond? >> you know, i think that's true of every president.

people ask, you know, what do you think about this issue or that issue? i say, i don't know. we don't know how it will play out yet. you look at something like health care. we've provided 20 million people with health insurance. the affordable care act, obamacare, for those 20 million people their lives are better. now if 20 years from now we look back and despite efforts by the republican congress to roll it back, we end up seeing that it set the bar. it was sort of the starter home for everybody in this country getting the health insurance that they need and us continuinging continuing in to make progress and reducing costs, we'll say we're sure glad the president got that started. if it gets completely reversed and 20 million people, and maybe

it's doable and that carries the conversation forward to a new administration. >> now he watches day by day as the next administration threatens to dismantle his legacy, but his oaudacity to hope, he says, endures. >> we've shown what's possible and the promise of our democracy is not that every gain we make is permanent. each successive generation has to reinforce our best impulses and try to do something about our worst impulses, and we -- we make progress and sometimes we take a step back before we start going forward again, but that's want a cause for despair. that's a cause for hope. >> we, as a people, will get there. >> which brings us back to grant park. >> yes, we can!

yes, we can! yes, we can! >> did you see some idealism in that young man? >> i did, and that idealism hasn't left. look, i'm grayer. people like to note the additional wrinkles. although i'm probably in better shape now than i was in that video. i'd been campaigning on the road for a year and a half, but my spirit is unchanged. it's undaunted. >> mr. president, thank you so much. and you've got a speech to make. >> i do. i don't want to be late. >> hello, chicago! ♪ ♪ >> i'm asking you to believe not in my ability to bring about change, but in yours. i am asking you to hold fast to that faith written into our founding documents, a creed at the core of every american whose story is not yet written. yes, we can. yes, we did.

yes, we can. thank you. god bless you. may god continue to bless the united states of america. thank you. ♪ ♪ all right. >> we are showing you what's happening live right now as hundreds have gathered in warren, michigan. they're calling to save the current health care system. this is just one of 70 similar, vents across the country coming just days after congress started repealing obamacare. we'll bring you a live report from that scene in just minutes from now. hello to all of you, i'm alex witt at msnbc world headquarters. it is 1:00 p.m. in the east and 10:00 a.m. in the west. trump's latest rift with the intelligence community. >> if he doesn't have confidence in the intelligence