Return to Transcripts main page

ERIN BURNETT OUTFRONT

President Obama Arrives in Chicago for Farewell Speech; Intel Chiefs Presented Trump with Claims of Russian Efforts to Compromise Him; Awaiting President Obama's Final Speech to the Nation. Aired 7-8p ET

Aired January 10, 2017 - 19:00   ET

THIS IS A RUSH TRANSCRIPT. THIS COPY MAY NOT BE IN ITS FINAL FORM AND MAY BE UPDATED.


WOLF BLITZER, CNN ANCHOR: An important day in Washington today, another important coming up tomorrow. That's it for me. Thanks very much for watching.

[19:00:02] I'm Wolf Blitzer in The Situation Room. Erin Burnett OUTFRONT starts right now.

ERIN BURNETT, CNN ANCHOR: OUTFRONT next. A very special edition of OUTFRONT. The President bidding farewell to the nation tonight. After eight years, President Obama returns to where it all began, right here. We are live in Chicago tonight. Let's go OUTFRONT.

Good evening. I'm Erin Burnett. OUTFRONT tonight. Breaking news. It is the final farewell for President Barack Obama, the 44th President of the United States, arriving just moments ago here in his hometown of Chicago to give his final address to the nation. In this hall before some 20,000 friends and supporters who will gather here in Chicago at the President's side tonight, the first lady. Tomorrow morning's return trip to the White House will mark their final scheduled trip on board air force one. And there is a lot of excitement here in the air tonight, people getting ready, people filing in hours early. Free tickets to this historic speech. Of course now some selling up to $5,000 according to the Chicago Sun- Times tonight.

The President has been planning his good-bye speech himself. He has been doing it for weeks and we are old he's gone through at least four drafts, even making last-minute edits on the flight here. The presidential farewell address is a tradition that goes all the way back to George Washington. This will be the first given by a departing president from his hometown. Barack Obama's presidency historic was born in this city here on election night in 2008 in Chicago's Grand Park.

The newly elected president we all remember, a quarter million people there to hear him, his young family at his side declaring in his words that, "Change has come to America." President Obama leaves office riding on a wave of popularity. It is his highest approval rating tonight in seven years. Tonight's speech will focus on his vision for the future. And he gave a small preview on Facebook today, he wrote, and let me quote him, "Over the course of my life I have been reminded time and again that change can happen, that ordinary people can come together to achieve extraordinary things.

We've made America a better, stronger place for the generations that will follow." We are counting down to the full address to President Obama's farewell speech. And we begin with Michelle Kosinski, she is right here with me in Chicago at McCormick Place where are gathered. And Michelle, this is a speech as we just reported. He was even editing on the flight here. He's now here in Chicago. What can we expect from him tonight?

MICHELLE KOSINSKI , CNN WHITE HOUSE CORRESPONDENT: Yes. You know, we -- he's been working on this for upwards of a week, at least. You mentioned the draft that he's gone through and you can imagine the task at hand. I mean, trying to encapsulate all that's happened in eight years, trying to touch on what just happened in America with this election, and then moving forward. So, the way the White House has framed it is that he wants to strike an optimistic tone. He wants to look at the challenges America faces moving forward. He wants to propose the best ways in his view to tackle those challenges. He wants to offer advice, you know, part of that of course is to the next administration but also to everyday people out there.

And the White House released just a few excerpts of his speech and he talks about where he came from, his roots, you know, starting out here in Chicago, talking about how ordinary people working together is how change happens, how things get done. So, the White House says he wants to focus on American values, on diversity, on hard work, fairness, and justice, and pull all that together somehow into one approximately half-hour-long speech. I think it will be interesting to see how he touches on the divisions in America. Does he touch on race, does he touch on what happened during this election. Because as we saw him out so many times, an unprecedented effort on the campaign trail trying to boost his own record but also trying to say that America really isn't as divided as some say. He kind of stopped talking about that so much as it got down to it. So how will he address those very real divisions right now, Erin.

BURNETT: All right. Michelle, thank you very much. As your hear Michelle say going to be a half an hour. Obviously there's going to be a lot of performances as well here in McCormick Place tonight. OUTFRONT now, Doug Brinkley, our presidential historian, Stephanie Cutter, the former Senior Adviser to President Obama, David Axelrod, also former Senior President -- Senior Adviser to President Obama. He has been helping the president with tonight's address. Austan Goolsbee, the former chairman of President Obama's council of economic advisers, Lynn Sweet, the Washington Bureau Chief of the Chicago Sun- Times, who's covered then Barack Obama well before he was president. Keith Boykin, former Clinton White House Aide and Kayleigh McEnany, a conservative columnist.

So David, let me start with you because I know you have been working with him on the speech. I heard four edits and I figure it's probably been a lot more than that. Well, it's probably a figurative process again and again and what's in it.

DAVID AXELROD, FORMER SENIOR ADVISER TO PRESIDENT OBAMA: Yes. I've had a couple of conversations with the speechwriters and I chatted with the president. You know, I'm struck by the fact you noted George Washington's speech and he set the tone for these farewell addresses. And his message to the nation was that there was strength in unity and the greatest threat to our country was disunity. I suspect there will be echoes of that in this speech tonight. I think that tonight is not going to be a night for doing victory laps so much as talking about the future and talking about our democracy and what we have to do to keep it strong and vibrant. And I think that's going to be the essence of what he talks about.

BURNETT: Is he emotional? A lot of people in this room are going to be will be moved to tears tonight.

AXELROD: Ye, yes. You know, I - it's funny, I have a drawer full of credentials that go back to the first events that we held in 2007. And tonight I came and picked up my credential and said the president's farewell address and I got choked up just picking that credential up. So there of course is going to be that feeling in the room and he's going to feel it himself. There's an emotional connection to Chicago and to come back to where it all began. How can -- how can you not?

BURNETT: Right. I mean, you would think, and so many of you were here at that beginning. I mean, Stephanie, you have been -- you were, you know, with him at the beginning. You know, we understand he wants to recall and change, right? That was his mantra. That was what swept him to the White House. Donald Trump now of course is going to be coming into the White House. Did Trump's win affect his message tonight, what he's trying to say, how he feels as opposed to it being a victory lap versus something else?

STEPHANIE CUTTER, FORMER SENIOR ADVISER TO PRESIDENT OBAMA: Well, I -- David would know that better than I would. But I would imagine that tonight is a little bit of a different speech than he would have given if Hillary Clinton had won the presidency. You know, we're at a -- we're at a critical time in our country and hope and change, we know -- we need help and change more now than ever. And I think the president -- as David said, it won't be a victory lap, but we -- he will talk about some of the change he has brought about bringing -- and making this country a much more fair and just country. And I think it will be a message looking forward about we need to stay the course and all of us can effect change.

And just - for who have -- may have lost the election, don't give up. We can still effect change. For those that won the election, let's work together. So, I think that's the kind of message we'll hear tonight.

BURNETT: And the significance of where we are. You know, just today, spending a few hours before this -- before this event, you saw the people coming to hear him speak. These are his passionate supporters, people who love him, you know, we saw someone with a My Brother's Keeper jacket on on the back, you know, this is an emotional night for them but this is very significant. These addresses are usually given from the oval office, almost always, in fact. And never from an adopted hometown as Chicago is for him. DOUGLAS BRINKLEY, CNN PRESIDENTIAL HISTORIAN: Always given by -- from the oval office or a State of the Union Address that might count as a farewell. George Herbert Walker Bush gave a speech at West Point that some consider his farewell address. Nothing like this. This is a rock 'n' roll concert, a political rally. The energy level is high and the amount of love in this city for the president that's coming back here to this presidential center is just sky-high.

AXELROD: I think one -- I think one of the messages of having it here is what Stephanie spoke of. He believes change begins from the bottom up. So to mark this moment with sort of grassroots folks who have supported him from the beginning underscores that message about the vitality of democracy.

BURNETT: And Lynn, you know, you've covered him from the very beginning. You know, before he was running for president, you've known him for a very long time. You know, he and his wife left Washington tonight, the first -- the last time that they expect to leave Washington as President and First Lady of the United States. A final flight on air force one. How emotional is this for them and their daughters?

LYNN SWEET, WASHINGTON BUREAU CHIEF, CHICAGO SUN-TIMES: Well, if I'm guessing what it is, is that this is the only thing their daughters have known, really.

(CROSSTALK)

BURNETT: Yes. They were so very young. Yes.

SWEET: And we remember when (INAUDIBLE) tonight the pictures from Grand Park and the girls are this high and now they're grown-up young women now. But how could you not be emotional? Because this is -- this is not just the -- this is not just the president's journey. This is the family's journey. This is Mrs. Obama's journey who also (INAUDIBLE) ended up as a very popular first lady. You know, she'll make her final public appearance not tonight but tomorrow tonight on Jimmy Fallon where she has shown she is a terrific -- you know, a terrific personality that she has grown in to from as Stephanie well known, tentative as she was at the beginning of the first term of even getter her to do some shtick, everything was a little more (INAUDIBLE) thought out, cautious, to where she now has fully embraced social media and is kind of the --

BURNETT: I should say the most popular democratic voice in this country. I mean, that was -- that's pretty clear. But (INAUDIBLE) also though, the importance of Chicago tonight, you know, it's a town that he may come back to. Next year of course he's going to be living in Washington, which carries his own level of awkwardness. He thought that would be with the President Hillary Clinton, now it's to the President Donald Trump. But this speech tonight is in a city where murder rates have surged in the past year. You know, we talked to community activist last night, there is a lot frustration among some here and they say he didn't do enough for the city. Does he feel a guilt or an obligation, you know, a reason he wants to be here tonight? AUSTAN GOOLSBEE, FORMER CHAIRMAN, COUNCIL OF ECONOMIC ADVISERS: Probably an obligation and, you know, it's got both sides. The magic of Grant Park and that wasn't far away from where we're sitting tonight. But, you know, of all states in the union, actually the state of Illinois is the most resembling of the nation as a whole, a microcosm. I think it's totally appropriate that he would do it here. The country as you know, Erin, tends to grind up our political leaders while they're in office and then tends to venerate them when they leave. And you can see in the --

BURNETT: Well, you've seen his approval ratings just surged, right?

GOOLSBEE: That's -- as we come to the end of the administration, you can see it on the faces of the people in the audience here. I think, he's a decent man. He's confronted by a lot of tough challenges and he did a good job in my opinion.

BURNETT: I mean, you can see the setup. It's going to be 20,000 people in this room. They've been queuing for a long time to get inside. The emotion of the people coming here. What I saw a lot of young people, a lot of people under 30. I mean, I'm not going to say it's represented about the 20,000, we'll see, but they are coming in droves.

KEITH BOYKIN, FORMER CLINTON WHITE HOUSE AIDE: I think that's right. I think he is -- he is representing not only a youth generation but a lot of people who saw hope and change in his administration and in his campaign. You know, I've known Barack Obama since we were both young, we were law school together, and to see him be Elected president --

BURNETT: I have to say, Keith, maybe it's that you don't have hair, but the presidency really ages him, you do not look a lot --

BOYKIN: He look good. He was a year-- he was a year ahead of me though. But, you know, just to watch this young man who grew up from being editor of the law review to become the President of the United States and now, eight years later here he is, coming to the end of his administration. This is a sad moment for me. And to know that his administration will be book ended by two republicans, you know, George W. Bush before him and Donald Trump after him, it adds a certain sense of somberness to it as well.

BURNETT: Does he feel any sense of defeat because of that?

BOYKIN: I don't think he's someone who feels a sense of defeat. I think he reflects on events and thinks about how to move forward. You're going to hear that tonight. I think -- as Michelle said, I think there's going to be an optimistic tone to this. But, you know, I do want to mention about Chicago, yes, if you go north, you get to grant park where he accept the -- if you -- if you go -- if you go a few miles south, you go to -- you're in the neighborhoods where he came when he first came as young man to become a community organizer in the shadow of close steel mills where he faced all kinds of despair and helped forge small victories. And he's not a guy who feels defeat. He's someone who looks for ways forward. BURNETT: All right. And that's the feeling we're going to have. Well, you all are staying with us of course as we're counting down for this moment in history as it is, the farewell speech of Barack Obama, our president.

Coming up, major breaking news. A CNN exclusive report. Intelligence officials presented Donald Trump with claims of Russian efforts to compromise him. The breaking details coming up.

Plus tonight, also a farewell to the first lady and the two little girls who are now two very striking and very successful young women. And the highs and lows of eight years in office. What will President Obama's legacy be? We are standing by for his farewell address to the nation here in Chicago.

(COMMERCIAL BREAK)

BURNETT: Welcome back to the very special edition of OUTFRONT. We are live in Chicago tonight just moments away from President Obama's farewell address to the nation. We have breaking news in the nation's capital tonight though that we need to tell you about, I want to go straight to Jake Tapper who is joining me now from Washington. Jake?

JAKE TAPPER, CHIEF WASHINGTON CORRESPONDENT FOR CNN: Thanks, Erin. We have a CNN exclusively for you now. CNN has learned that the nation's top intelligence officials provided information to President- elect Donald Trump and to President Barack Obama last week about claims of Russian efforts to compromise the President-elect Donald Trump. This information was provided as part of last week's classified intelligence briefings regarding Russian efforts to undermine the 2016 U.S Elections. Jim Sciutto, Evan Perez, and Carl Bernstein and I have been working on this story. I'm going to bring in my colleagues right now. And Jim, walk us through the basic story of what we know.

JIM SCIUTTO, CHIEF NATIONAL SECURITY CORRESPONDENT FOR CNN: OK. Let's begin here. Multiple U.S. Officials with direct knowledge of these briefings tell CNN the classified documents on Russian interference of the 2016 U.S. Election presented last tweak to President Obama and President-elect Trump included allegations that Russian operatives claimed to have compromising personal and financial information about Mr. Trump. The allegations were part of a two-page synopsis based on memos that compiled by a former British intelligence operative whose past work U.S. Intelligence officials consider to be credible.

The FBI is investigating the credibility and accuracy of the investigations now which are based primarily on information from Russian sources but is not yet confirmed. Many essential details in the memos about Mr. Trump. Those classified briefings last week were presented by four of the most senior intelligence chiefs, Director of National Intelligence James Clapper, the FBI Director James Comey, CIA Director John Brennan, and NSA Director Admiral Mike Rogers. The two- page synopsis also included allegations that there was a continuing exchange of information during the campaign between Trump surrogates and intermediaries for the Russian government. This according to two national security officials. CNN has confirmed that the synopsis was included in the documents that were presented to Mr. Trump.

We cannot confirm it, it was discussed in his meeting with the intelligence chiefs as well. To be clear, the Trump transition team will reach out to them, so far they declined to comment, as did the officer of the director of the National Intelligence of the FBI but Jake, I know that you're reaching out for a comment from the Trump --

TAPPER: Yes. The Trump team, we reached out to them, earlier today. We are still waiting for them to give us a comment -- a response to this information that CNN broke earlier today. I just want to put a button on the point you said, that this synopsis was an addendum to the intelligence community report on the hacking, it was not part of it.

SCIUTTO: That's right. The intelligence community report on the hacking focused on did Russia hack the election? That's, their assessment, yes. Why did they do it? Their assessment is the intent was to help Donald Trump. This was appended to that, focused on these allegations of personal and financial compromising information about Mr. Trump. So not part of that initial and overall assessment.

TAPPER: So Evan Perez, let me bring you in here because what we have here are allegations being made by Russians and the Russians are saying, A, they have compromising personal and financial information about the President-elect. And B, that they had exchanges of information with the with the Trump campaign team throughout 2016. But what the intelligence officials did not do is say we know that these things are true. They say that Russians are claiming it, that they believe. Why bring up this information if the FBI and the intelligence community is still investigating it and hasn't corroborated it? Why bring it to the President-elect?

EVAN PEREZ, CNN JUSTICE CORRESPONDENT: Well Jake, they did it for a couple reasons. The intelligence chiefs decided to include these summaries in other -- in a way to remind Donald Trump that they -- this information was out there, that these allegations involving him were circulating among some of the highest level officials including intelligence agencies, members of congress, government officials in Washington. Now, several officials with knowledge of the briefings tell CNN that the information was also included in part to demonstrate that Russia had compiled information potentially harmful to both political parties but only released information damaging to Hillary Clinton and the democrats.

Now, this synopsis was not an official part of the report as you mention from the intelligence community and as you know, that was focusing on the Russian hacks. But some officials said that it augmented the evidence that Moscow intended to harm Clinton's candidacy and help Donald Trump.

TAPPER: Let me bring in the legendary Carl Bernstein right now because Carl, this information did not start with U.S. Intelligence officials or with the FBI or U.S. Law Enforcement officials. Where did it come from originally?

CARL BERNSTEIN, AMERICAN INVESTIGATIVE JOURNALIST: The information was developed by a former British MI6 Operative with great experience in the former Soviet Union and Russia and he had been hired by a Washington opposition research group that in turn had hired -- had been looking for information about Trump for clients who were opposed to Trump's candidacy in both the republican and democratic parties. And as they developed in Washington this information about Donald Trump's business ties in Russia, the Russian businessmen, it began to look to them as if there were a deeper story. They hired the former MI6 guy in London.

He went to his sources, sources over many years apparently that he'd cultivated in Russia, and they began to tell him ostensibly about their knowledge of relationships with Donald Trump, with businesses that he was associated, and it became a ball that started rolling from there if we are to believe these assertions. And then at a certain point, the MI6 man in London thought the information was sufficient to take to the FBI himself. He walked it into an FBI station in Rome where he knew a colleague in the intelligence business in August, gave him the information. It came back to Washington.

And then subsequently a former ambassador to Russia from Great Britain also became aware of this information, brought it to the attention of Senator John McCain, a 35-page report prepared by the MI6 agent of these purported allegations. And McCain thought it sufficient and serious enough that he took it to Director James Comey of the FBI himself. They had a five-minute meeting. And It has been left at the FBI by Senator McCain and people are waiting to see what these investigations are going to produce.

TAPPER: Interesting in October, Senator Harry Reid was then the senate democratic leader, he wrote a letter to James Comey, the director of the FBI, after a classified briefing. Harry Reid at the time was one of the so-called Gang of Eight, that's the congressional leaders and the -- and the chairman and ranking democrat of the intelligence communities in the house and senate. And he said to Director Comey in this letter that he released publicly, you possess explosive information about close ties in coordination between Donald Trump, his top advisers, and the Russian government, a foreign interest openly hostile to the United States, which Trump praises at every opportunity.

Today Harry Reid reached out -- Harry Reid's spokesman issued a statement saying Harry Reid's -- in response to our reporting, Harry Reid's statements and letters from last year speak for themselves. Who else would know this information, Jim?

SCIUTTO: OK. To be clear, as we've established, intelligence community has it, they're investigating. The FBI has it, they're investigating. We also know that senior congressional leaders have it, the same day the President-elect got his briefing, you have the so-called Gang of Eight. These are the top four congressional leaders as well as the chairman and ranking members of the house and senate intelligence communities, this Gang of Eight, they were provided with the same summary, the synopsis of the memos but to be clear, this gets to the sensitivity. Only the president, the President-elect and that Gang of Eight got this synopsis. It was not included in the report that was shared more broadly with members of congress. And that gets to the sensitivity here. That said, and we've said this a number of times, the essential allegations in there have not been confirmed. But agencies are looking at them.

TAPPER: And one of the most interesting subtexts going on today, Evan Perez, was the senate intelligence committee had a hearing today about Russian hacking. And it seemed as though members of the senate intelligence community had heard some of this, at least about whether or not any campaign was working with the Russian government and -- well, let's run a clip. There's this part of the -- of the hearing.

Senator Ron Widen asked the FBI director if he could say anything about it. Comey, the FBI Director kind of dodged and then senator Angus King, an independent from Maine, he went back and did a follow- up on behalf of his colleague, putting it again to FBI Director Comey.

(BEGIN VIDEO CLIP)

SEN. ANGUS KING, (I), MAINE: Mr. Comey, did you answer Senator Wyden's question that there is an investigation underway as to connections between either of the political campaigns and the Russian -- Russians?

JAMES COMEY, DIRECTOR, FBI: I didn't say one way or the other.

KING: You did say that --

COMEY: That was my intention, at least.

KING: You didn't say one way or another whether even there's an investigation under way?

COMEY: Correct. I don't -- especially in a public forum, we never confirm or deny a pending investigation.

ANGUS: The irony --

COMEY: I'm not saying --

ANGUS: The irony of your making that statement here, I cannot avoid. But I'll move on from that.

COMEY: Well, we sometimes think differently about closed investigations.

(END VIDEO CLIP)

TAPPPER: That at the end there was this little reference to Director Comey's comments about Hillary Clinton's investigation into here. But let's move on. It seems as though members of the intelligence community want the FBI Director to be a little bit more forthcoming about whether or not clearly they think the Trump campaign was coordinating or at least whether or not this is being investigated, with Russia.

PEREZ: Right. And I think Comey was definitely not going to answer that question in an open setting. And he even said, you know, in a classified setting I could perhaps provide you with more information. We know that the FBI has been taking a look at whether or not there were contacts between surrogates of the Trump campaign, people surrounding the Trump campaign and people who are intermediaries of the kremlin. And it is something that is a broader investigation and again, this is the top of the list of concerns for the intelligence community as well as for the FBI.

They want to know whether or not the intelligence activity of the Russian government -- how far it extend. And I think this is of utmost importance. Again, we're not saying that they found anything and -- certainly how far it goes, but it is something that has drawn their interest and it's an -- it's an ongoing matter. And since the election, it is definitely something that has back up and running.

SCIUTTO: And we snow that senators both democrat and republican, they also want to dig deeper, particularly on these alleged communications between the Trump campaign, surrogates, and Russian government officials during the campaign.

TAPPER: And Carl Bernstein, let me -- let me bring you back just to -- what possible reason do intelligence experts you've spoken with, what do they think is the purpose behind these top intelligence officials telling Donald Trump and president Obama there is all this information out there and it comes from sources that we've checked out and they seem credible and our sources' sources also seem credible?

BERNSTEIN: It seems possible that there is a determination by the senior officials of the intelligence community in Washington to ensure that this event, these reports are thoroughly investigated. We have a new administration coming in. Some of these officials might not serve in the new administration. And it seems that they laid down markers that will make it impossible for their successors not to follow through with investigations. They deem it serious enough, these assertions, that they want to see that it's investigated in the new administration.

TAPPER: All right. Carl Bernstein, Evan Perez, Jim Sciutto, thank you so much. Erin Burnett in Chicago, back to you.

BURNETT: All right. Thank you very much, Jake Tapper. Obviously a crucial breaking news report.

Meanwhile here, we are awaiting president Obama. We understand he is at a local restaurant here in Chicago.

[19:30:01] He is now going to come where we are as we count you down to his good-bye address to the nation, his farewell speech tonight.

Plus, Michelle Obama, her equally historic eight years as first lady. Perhaps the biggest question is what is next for her.

And some memorable moments from the Obama years, including his emotional words after the massacre at Sandy Hook Elementary School.

(BEGIN VIDEO CLIP) BARACK OBAMA, PRESIDENT OF THE UNITED STATES: Every time I think about those kids, it gets me mad. And by the way, it happens on the streets of Chicago every day.

(END VIDEO CLIP)

(COMMERCIAL BREAK)

BURNETT: And we are live in Chicago tonight. President Obama will be saying good-bye to the nation tonight, right where we are in this room. The first time a departing president has given the farewell address from his, in Barack Obama's case, his adopted hometown. He is going to take the stage shortly.

First, though, Michelle Kosinski OUTFRONT on the triumphs and some of the disappointments of President Obama's eight years as president.

(BEGIN VIDEOTAPE)

MICHELLE KOSINSKI, CNN WHITE HOUSE CORRESPONDENT (voice-over): It is a homecoming and a good-bye. Chicago crowd, some 20,000 strong, will see President Obama deliver his farewell speech where his political career began.

[19:35:07] UNIDENTIFIED FEMALE: I might cry, I might cry.

KOSINSKI: Some waiting here 14 hours.

UNIDENTIFIED FEMALE: I have been successful for the last eight years because of this man. And I'm going to continue to be successful because of his legacy.

KOSINSKI: In those eight years that made history and the president rarely misses a chance now to lament the loss of his boyish looks and dark hair back then.

OBAMA: I was a skinny guy with a funny name. When I look back at the pictures of me speaking back then, I look really young.

KOSINSKI: From his victory speech --

OBAMA: Because of what he did on this day, in election, at this defining moment, change has come to America.

KOSINSKI: To the winding down.

This has been a presidency both acclaimed and derided in a starkly divided America.

OBAMA: It's one of the few regrets of my presidency, that the rancor and suspicion between the parties has gotten worse, instead of better.

KOSINSKI: The president's most applauded actions has also been great controversy, among his proudest accomplishments -- the weathering of America's economic crisis.

Also on his list: the passage of Obamacare, the killing of Osama bin Laden, the Iran nuclear deal, the reopening of relations with Cuba.

But during that time, Congress turned when both houses went Republican in his second term, President Obama's executive actions --

OBAMA: I've got a pen and I've got a phone.

KOSINSKI: -- riled Congress even more. His immigration plan now on hold. Obamacare about to be dismantled.

President Obama ended America's two long wars but found himself embroiled in another against ISIS. Not long after those often-quoted words calling it a jayvee team.

President Obama's administration saw the historic Supreme Court decision legalizing gay marriage, though Congress blocked his latest choice to sit on that court.

On education, high school graduate rates at an all-time high and President Obama has made it his mission to expand access to college to try to close gaps between rich and poor, black and white.

OBAMA: I'm here to insist that we are not as divided as we seem. I know that because I know America. I know how far we've come against impossible odds.

KOSINSKI: His strongest emotion broke through whenever he spoke about gun violence, the limits on his ability to restrict access to high- powered weapons.

OBAMA: And from every family who never imagined that their loved one would be taken from our lives by a bullet from a gun -- every time I think about those kids, it gets me mad.

(END VIIDEOTAPE)

KOSINSKI: You know, we saw this unprecedented effort by him on the campaign trail for Hillary Clinton, but of course he was also fighting for his own legacy. So, that defeat was a blow for him too.

Tonight, he, obviously, wants to seize on optimism, on looking at ways forward. He's leaving office a very popular president. I mean, his latest approval ratings are approaching Bill Clinton numbers, but he's absolutely been buffeted by these strong winds of change, division, and uncertainty, Erin.

BURNETT: All right. Michelle, thank you very much.

And my panel is back with me here as we are just waiting for the president to arrive. Bill Burton also joins me, former deputy press secretary under President Obama.

So, Bill, let me start with you, because his signature piece of legislation is Obamacare. At first, Republican dubbed it as an insult. He embraced it. He took it on as his own.

The president-elect told "The New York Times" today, quote, "We have to get to business. Obamacare has been a catastrophic event."

How big a blow will it be to President Obama if this is the first thing to go, Obamacare?

BILL BURTON, FORMER DEPUTY PRESS SECRETARY UNDER PRESIDENT OBAMA: Well, I think if the president we're talking here right, what he'd say it would be a big blow to the American people much more than him personally.

You can't overstate how hard it was to get health care done. And, you know, we went through these long periods of time where people thought it was dead. I wish David Axelrod was still here. There's this one time when we were prepping Robert Gibbs for his briefing, and I said to Axe, what should Gibbs say if he's asked the question, is Obamacare dead? And without missing a beat, Axelrod goes health care's not dead, it's just sleeping.

But it came roaring back. And now, I think President-elect Trump and the Republican Congress is going to have a very hard time if they think they can get rid of a system of health care, where it protects people that have pre-existing conditions, it allows kids to stay op health care for longer and going back to a place you could get denied health insurance because pregnancy is considered a pre-existing condition is going to be a very difficult political thing for Trump and Republicans who do let alone completely senseless.

[19:40:02] BURNETT: And Trump is aware of this, Kayleigh. He's actually afraid of all of a sudden, they do something and all the faults of Obamacare become Trump care.

KAYLEIGH MCENANY, CNN POLITICAL COMMENATOR: That's right. And I thin we saw President-elect Trump cite that on the debate stage. He acknowledged that those popular parts of Obamacare needed to stay, pre-existing conditions, allowing kids to stay on the healthcare plan.

But he has a monumental task ahead of him, and so does the Republican Congress. Healthcare is 18 percent of our economy. You can't just take this system away that has millions of people healthcare without a replacement. So, Republicans have a big task on their hands to come.

BURNETT: Stephanie, we saw him at Sandy Hook, a time where was crying and I think reflecting how the nation felt. And it was incredible how quickly that nation went from that moment to doing absolutely nothing about gun reform. It affected him emotionally. He has spoken at gun attack after gun attack since then with increasing anger.

Here he is.

(BEGIN VIDEO CLIP)

OBAMA: The majority of those who died today were children, beautiful little kids between the ages of five and 10 years to old. Once again, innocent people were killed in part because someone who wanted to inflict harm had no trouble getting their hands on a gun. This is a political choice that we make, to allow this to happen every few months in America. These kinds of tragedies have happened too often during the eight

years that I've been president.

(END VIDEO CLIP)

BURNETT: He has signed executive actions, Stephanie, again and again, but not a single law has changed. How does that affect him? This mattered deeply to him. Not one law has changed in his eight years.

CUTTER: Well, I think that there are few things. If anything that frustrates him as much as the lack of action on gun safety, particularly when you're talking about first and second-graders who lost their lives because of the lack of gun safety.

You know, and the fact that the reason we don't have it is because of just pure politics makes it worse. So, you know, it will be interesting to see if he speaks about it tonight, about how we address violence in this country. But I think if you're looking back over the past eight years, gun safety, gun control would be top five if not top two on his list.

BURNETT: I mean, as -- do you think he will bring it up tonight? Because when I say executive action, that means Donald Trump can undo all of these executive actions on day one. And he has indicated, in fact, that many of them, that's exactly what he will do.

GOOLSBEE: Look, I think he will do that. I don't know if he'll do it on guns. Not, you know, the broad center of the country seems to be in some agreement about preventing the violently mentally ill from getting weapons, trying to prevent terrorists from getting weapons. Hopefully, we can find --

BURNETT: Of course, it happened in Ft. Lauderdale again on Friday.

GOOLSBEE: You know, with a lot of executive orders I kind of think President Trump is going to experience his Obi-Wan Kenobi moment, you know, you remember in the "Star Wars" movie, Darth Vader comes out to fight the light saber battle and he just stands there and he says, if you strike me down now, I shall become more powerful than you ever imagined.

And I think the more he gets rid of, then when things go wrong -- remember when Obama comes into office, the economy is not doing well, epically bad. As we have turned that around to be something more solid when we didn't have a depression, any stumble in the economy people are going to say what did you do, Donald Trump? It was going well when you took over. And so, I think they know that, they're going to have to think about it.

BURNETT: And, Keith, on this issue of the economy, because you and Austan deal with this a lot. Look, millions of jobs net have been created since Barack Obama took office, right? Not just getting back to even, net jobs created. And yet we saw in this election, people didn't feel it. People didn't feel it. He does not get credit for that job creation because people didn't feel the wealth creation. BOYKIN: I think that's partly true. I think people -- the Democrats

didn't do a good enough job, I think, in telling the job creation that's taking place. I remember when Ronald Reagan declared there was morning in America 1984, unemployment was higher than it was -- it was 7.8 percent. Unemployment is now 4.7 percent. He gets no credit for that. Everybody has all kinds of excuses about why that's not acceptable.

But the reality is we were losing 800,000 jobs a month and now, we're gaining almost 200,000 jobs a month. I think President Obama tonight, I hope he at least -- David says he's not going to take a victory lap, but only at least acknowledges that yes, we are better off than we were eight years ago. Ronald Reagan used that.

BURNETT: One other point I want to make, many promises he made, things he cared about. One of them was the Middle East, right? That much vaunted speech in Cairo. A very historic and unprecedented moment in and of itself. He had a huge goal for the Middle East, many of them.

Here's what he said in Cairo.

(BEGIN VIDEO CLIP)

OBAMA: The only resolution is for the aspirations of both sides to be met, through two states where Israelis and Palestinians each live in peace and security.

(END VIDEO CLIP)

[19:45:10] BURNETT: Eight years later, no resolution on that issue. Israeli settlements have expanded dramatically, 500,000 in the West Bank according to Human Rights Watch. You have ISIS, you have Syria, you have Russia in Syria. This is an area of his legacy that at least at this point has not lived up to any of the hopes and promises that he has.

BRINKLEY: Very hard to get a good policy coming out of the Middle East and this stage. I mean, Barack Obama famously gave his Nobel Prize speech talking about used of drones or having to go into warfare with a new kind of way. But he gets credit for getting us out of Iraq, getting us out of Afghanistan, but the hope of Arab spring fizzled. The Facebook revolution that was going to happen with young people on the streets, that boomeranged, and instead became recruiting tools for ISIS.

And I think the low moment of Obama's presidency may be in Syria, the line drawn in the sand not met. However --

BURNETT: The red line.

BRINKLEY: The red line, but not sending in troops in the long run might be seen as the right thing.

BURNETT: Well, as we get ready for the president, as I said, coming here momentarily, he's at a restaurant, the Valois, or Valois, as you would say, nearby.

UNIDENTIFIED MALE: It's a good place.

BURNETT: You all know it out here from Chicago.

SWEET: And it's near where his home is, near the University of Chicago is.

BURNETT: And he's going to be there, he is there right now, with Michelle Obama. And tonight, perhaps, an equally important moment for her. Here's what she said just a couple of days ago.

(BEGIN VIDEO CLIP)

MICHELLE OBAMA, U.S. FIRST LADY: Being your first lady has been the greatest honor of my life and I hope I've made you proud.

(APPLAUSE)

(END VIDEO CLIP)

BURNETT: And that was the first lady. Very emotional, delivering her final address at the White House just a few days ago.

This is a family that is wildly popular across the country and obviously in Chicago as well.

Lynn, so let me just ask you, look, the first lady is even more popular than her husband, the most popular political figure in America. That what does tonight mean for her? She came into this so reluctantly and she has emerged as a political star in her own right.

SWEET: Well, part of this is, it's because with the help of people like Stephanie Cutter early on, she decided to make herself into a brand and she was very judicious, who she would talk to, what events she would go at. She was very careful as to where she would devote herself.

But more important, she picked four what in hindsight looked like terrific causes to be her initiatives. Let's Move, which is healthy eating and exercise. Joining forces with Dr. Jill Biden, who also will be here tonight, is helping military families and the families of veterans. Her Let Girls Learn, which is done domestically and globally. She also has an event with the arts.

Now, some of these organizations she's already set out, Erin, they have nonprofit structures, some of them behind them, so she could carry on with them. And, of course, let's remember literally the seeds of her popularity were planted with that White House garden which no one at the time knew would become in a sense her first major success in the White House, though no one knew at the time it would lead to this healthy eating and childhood crusade against obesity. So, it didn't happen by accident.

(CROSSTALK)

BURNETT: Reading the labels, for example.

But, Stephanie, she came in as a woman with an incredible professional success. And some say that rubs some people the wrong way and that she became much more successful as a first lady when she focused on her role as a mother and as a caregiver, which is obviously crucial to her, no matter whether she was a professional or not, but something that she then emphasized more and more. Here she is at the two conventions talking about her daughters.

(BEGIN VIDEO CLIP)

MICHELLE OBAMA: I come here as a mom, as a mom whose girls are the heart of my heart and center of my world. They're the first things I think about when I wake up in the morning and the last thing I think about before I go to bed at night.

You see, at the end of day, my most important title is still mom in chief. My daughters are still the heart of my heart and the center of my world.

(END VIDEO CLIP)

BURNETT: Will that be her legacy?

CUTTER: Well, you know, I have to say from the moment I met her early on in the early days, she was always a mom first. That was her primary concern, to make sure that those two girls could grow up and be whatever they wanted to be and to do it on their terms even in the public eye.

[19:50:03] You know, I think -- you know, I disagree with one thing that Lynn said. It wasn't with the help of people like me. Michelle Obama was a star from the beginning. The only difference was she fully intended to be a private person for her life yet was married to this person who would become president.

SWEET: I was paying you a compliment, Stephanie.

CUTTER: I know.

SWEET: That's what you do. You help people do this.

CUTTER: I know. Thank you.

But I just wanted to clarify that there is nobody -- I think few people would disagree with this, that knows how to communicate better, is more comfortable in her own skin and understands the position that she's in in terms of a responsibility to inspire young women across the country and over the world.

BURNETT: So, I threw this over then. What's next for her? Because when you say that, that naturalness, that is what she has. That, for example, Hillary Clinton does not have, right? And that was a big part of the problem about Hillary Clinton. Michelle Obama has the natural charisma and connectivity of a politician.

CUTTER: Michelle Obama -- but she is not a politician.

BURNETT: But she doesn't want to be one.

BRINKLEY: No, she doesn't. She also has integrity and grace about her. It's been extraordinary. She might be something do something like Oprah Winfrey's magazine, work on something about trying to get school kids moving, continue to help build a center here in Chicago in the South Side. She wanted it in the South Side, not on Lake Michigan where the tourists are going, but where her neighborhood she loves could revitalize itself.

So, she's going to be active in a grassroots way. And, boy, her memoir is going to be popular. It might even outsell Barack Obama's memoir. They'll each get paid quite a bit of money for them because they are two very popular people.

BURNETT: Yes, and let me just play -- you know, because she is very popular. She's going to be doing another late night show, her final good-bye. Here are some of her best moments.

(BEGIN VIDEO CLIPS)

(SINGING)

UNIDENTIFIED MALE: Oh, I mean, Beyonce.

MICHELLE OBAMA: What can we say? We just dropped the mike.

Don't tell people about my rash.

ELLEN DEGENERES, TV HOST: A rash that she has. Where is the rash? What area were you telling me about?

MICHELLE OBAMA: My shoulder.

DEGENERES: Lower than that.

(MUSIC)

(END VIDEO CLIP)

BURNETT: Keith, you've known her a long time. Is she going to miss that?

BOYKIN: I don't know. You know, the reality is I've not known her a long time. I met her when she became first lady. I never knew her in law school.

But she has this relatable personality. Even when I met her in the White House for the first time, she hugged me and embraced me like she'd known me for her entire life. I'll tell you, you know, as an African-American, it really has been a joy to watch her on this national stage.

I'm good friends with her hairstylist and we were just texting a few moments ago about what this means. She's become this icon in not only African-American culture but American culture.

BURNETT: With a much envied hair style and stylist, I should say. All of it, yes.

A quick word, something Melania Trump can learn from.

MCENANY: Just be yourself. That's what Michelle Obama did and that's why America loves her, the most popular politician on the Democratic side, arguably overall in either party. She's a very likable woman. She's very relatable and she was just herself. I think if Melania goes in and she's just herself, she'll have the same success.

BURNETT: All right. Thanks very much to all of you, as we get ready for the president next.

As we count you down to President Barack Obama's final address. We will hear from the people in the audience tonight who have been gathering all day on a foul and nasty day here in Chicago, they braved the elements to come here to see him. What do they want to hear from him in his final speech to the nation?

(COMMERCIAL BREAK)

[19:57:30] BURNETT: And we are here in Chicago. I'm on the floor of the McCormick Center, the president is going to be arriving here, giving his farewell speech.

I'm with DeLeon Watson, who -- this is a big moment for you, a big night for you. You're from Chicago, right?

DELEON WATSON, CHICAGO RESIDENT: I am born and raised in Chicago.

BURNETT: Born and raised in Chicago, and you supported the president since the beginning.

WATSON: I did. I got out and really rallied for this president from day one.

BURNETT: So, tell me how you feel to want. This is going to be a very emotional for you.

WATSON: It is for me. I mean, this country was in dire straits currently, and I think this man was doing a great job. And to see him leave is kind of difficult for myself, but I think the country is better off right now and he's still going to be there for all of us. I think that's where we are currently.

BURNETT: You know, the other day, we talked about a community organizer in Chicago, you know, there are some frustration where people feel the murder rate has gone up in the past year. He's visited the city 28 times. It's obviously a city he loves. But there's frustration that he didn't do everything he could for Chicago.

When you hear that, do you feel anything true about that for you or no? WATSON: Not at all. I think that as a president, you have to look

globally as opposed to citywide. You know, you can't put a president in one city and say he has to speak on a particular city just because that's where he's from. I think doing that gives doing him an injustice, considering his job is bigger than that.

For Chicago, he loves Chicago. His heart is here I'm sure and he'll do everything he can after his presidency. I'm sure he's done a lot of things during his presidency that will gate him into the way moving forward.

BURNETT: So, what are you listening for? We understand it's going to be about a half an hour. What are you listening for and do you think that there will be tears in your eyes tonight?

WATSON: I know there will be. Just being here is an emotional experience for me, one. But I'm looking to hear him say, America, let's rally around our new president, make this happen for all of us. It's not about one side, one party. It's all about everyone that's here tonight in this country, you know, the world.

We have to think about a global picture as opposed to just one particular party or person.

BURNETT: As much as you are a supporter of his, you want to hear him stay embrace Donald Trump, move on.

WATSON: I want to hear him to say, Donald Trump is our new president, I will support him wholly and I will give him my feedback as I see it and hopefully he accepts it. If not, you know, we'll continue to move in a direction that will accept us succeed.

BURNETT: All right. Well, DeLeon, thank you so much for being with us. And good luck tonight.

As you here see DeLeon, I think frankly looking a little emotional talking to me. A lot of people feel that way here on this floor. It's going to be a very, very emotional moment for so many here and so many across the country.

Thanks for watching, as we count you down.

Anderson is next.