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Anderson Cooper 360 Degrees

Obama: I Could Have Won; Trump Plans to Shutter Foundation; Israel Suspends Ties With Nations That Backed Up UN Vote; Remembering Pop Superstar George Michael. Aired 8-9p ET

Aired December 26, 2016 - 20:00   ET

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

[20:00:05] JIM SCIUTTO, CNN ANCHOR: Good evening, everyone. A very happy holidays to you. I'm Jim Sciutto. Anderson is off tonight.

President-elect Donald Trump is not. And we know that because he's just been tweeting again, taking a swipe at President Obama after the president answered one of those what-if questions that no one can resist. Namely, what if he had been running against Donald Trump? How would things have played out? Would they have played out differently?

President was asked that very question by his former senior adviser, David Axelrod. Late today Mr. Trump responded. His tweet in a minute.

First, what Mr. Obama had to say. The president telling David Axelrod that a majority of Americans still believe in his vision for the country and would have voted for it for a third time.

(BEGIN AUDIO CLIP)

BARACK OBAMA, PRESIDENT OF THE UNITED STATES: I'm confident that if I -- if I had run again and articulated it, I think I could have mobilized a majority of the American people to rally behind it. I know that in conversations that I've had with people around the country, even some people who disagreed with me, they would say the vision, the direction, that you point toward is the right one.

(END AUDIO CLIP)

SCIUTTO: Again, we will have direct reaction from President-elect Donald Trump shortly.

But joining our conversation now is the man who did that interview, David Axelrod.

David, really a fascinating, very personal interview. You, of course, had a very personal relationship with the president. But that comment standing out saying that he, Mr. Obama, could have gotten a majority of the American public behind his vision had he run again in 2016. Was that a dig at Hillary Clinton?

DAVID AXELROD, CNN SENIOR POLITICAL CORRESONDENT: Well, I don't think it was a dig at Hillary Clinton so much as a defense of where he thinks the country is and where the country is going. What he was making -- the point he was making is the country has not embraced the vision that Donald Trump has articulated because a majority of Americans, in fact, voted for Hillary Clinton and he believed that he would have won the election had he run against Donald Trump.

Now, he was critical after defending Hillary as having been the victim of unfair coverage, he did say that he thought the campaign may have taken too much for granted, may have played it safe and was particularly critical of not appearing in a number of those states that ultimately were lost enough and making the case enough in these rural communities and small towns. So, clearly, he felt that was a deficiency in the campaign.

SCIUTTO: Well, to that point, two deficiencies, as you know, the president likes to tell the story about the 2008 campaign, you know it very well -- rainy campaign stop, South Carolina, met that woman who led that small group in the now-famous "fired up, ready to go" chant. He tells that story in part to tell how he connected with people in small towns across the country, how they connected with him. It seems implicit in that in his interview with you, hinting, perhaps, that there wasn't enough of that with Hillary Clinton in this election.

AXELROD: Well, there's no question about it. He believes that the Democratic Party has a case to make to working-class Americans, white, black, Hispanic, Asian. But if you don't show up, you can't make the case and as he said, it's more than just policy, it's giving them the understanding that we believe for them that we wake up every day thinking about them and how we deal with some of the problems confronting their families and their communities. And clearly what he was suggesting in this discussion was that didn't happen in this campaign, and the result was a Donald Trump victory.

SCIUTTO: You're very close to President Obama. You talked to him about his personality. Also, why he's become the politician and the man that he is. You call him a friend. Going back 25 years. Helped him in the Senate, presidential campaigns.

I just wonder as you speak with him in this interview and elsewhere how personally did the president take the results of this election?

AXELROD: It was interesting because it was almost -- I almost was watching him puzzle through this as we talked in this conversation, but the way he reacted to it is very familiar to me. He tends to be very philosophical. He steps back. He considers things and then takes the long-range view.

And his conclusion was that America is moving in the direction of a more inclusive, progressive future, and that was reflected in the fact that a majority of Americans voted for Hillary Clinton and he said most reflected in the attitude of young Americans he meets all across the country that gives him confidence that the future's very much headed in the direction which he was leading.

SCIUTTO: He loved that line, the arc of history, long but bends toward justice, right?

AXELROD: Yes.

SCIUTTO: Now, in fairness, though, because you heard this about Hillary Clinton from some, even in the party who said she hasn't accepted responsibility for the mistakes she made.

[20:05:00] If you look at the numbers here, the Democrats have been losing power across the board virtually since President Obama first won back in 2008. I mean, big losses in the Senate, in the House, in state legislatures. That's going to be key, coming up to the 2020 census. Also in statehouses.

Does President Obama accept responsibility for that downward trend?

AXELROD: You know, Jim, I had this very discussion with him during this podcast and, you know, he did in a way accept it because he said we got to the White House, we were grappling with these problems, and suggested that perhaps we lost focus on that element of leadership but spoke very, very strongly about the need to retrench, to rebuild that strength at the statehouse level, at the legislative level, and to inspire young people to seek these offices.

So, implicit in what he was saying was we should have done this, we didn't do it, we have to do it now.

SCIUTTO: He also, perhaps, as a final point, talks about strength of his marriage. How Michelle Obama, a real force not just to help him through his personal time in the White House, raising kids, et cetera, through his political life.

AXELROD: Absolutely. His point on Michelle is that she kept him level. That she always was willing to tell him the truth. And what he knew about his wife, his children, and this cadre of very close friends he's had for a very long time is that they would love him whether he won or lost. And that, he found, was grounding for him as he went through these very challenging eight years.

SCIUTTO: David Axelrod, thanks very much.

AXELROD: Happy holidays.

SCIUTTO: You can listen to the rest of that conversation between Axelrod and the president by downloading the Axe Files podcast from CNN.com.

And as we said, Donald Trump gave his response tweeting it out a short time ago. Quote, "President Obama," he wrote, "said he thinks he would have won against me. He shouldn't say that, but I say no way! Jobs leaving, is, Ocare," Obamacare presumably, "et cetera."

A short time later, he threw in this jab, "The world was gloomy before I won. There was no hope. Now the market is up nearly 10 percent and Christmas spending is over $1 trillion."

On that note, let's bring in the political panel. Political strategist and former congressional Black Caucus executive director Angela Rye. Trump supporter and contributor to "The Hill", Kayleigh McEnany. Matt Lewis, who's senior contributor at the "Daily Caller", and "Washington Post" assistant editor David Swerdlick.

Matt, if I could begin with you, in effect, President Obama picking two fights here, one with Hillary Clinton, at least throwing a jab that way, but at Donald Trump saying, listen, if I'd gone up against you, I would have taken you down.

MATT LEWIS, DAILY CALLER: Yes.

SCIUTTO: I would have been able to keep that --

LEWIS: What a good political athlete should believe.

SCIUTTO: Yes.

LEWIS: Whether it's true or not.

SCIUTTO: Is it true?

LEWIS: That's one of those counterfactuals, would Joe Lewis beat Muhammad Ali, right? So, they're both heavy weights. And I think very clearly, Barack Obama is a much more charismatic, more talented politician than Hillary Clinton.

So, my copout answer I think, though, is this. If it's 2012, I think Barack Obama would have been re-elected and would have beat Donald Trump. But by the time you get around to 2016 as Donald Trump's tweet said, you have things like ISIS, you look at the Brexit vote, I think things were trending in Donald Trump's direction. I'm not so sure Barack Obama would have beat him.

SCIUTTO: Angela Rye, do you think this is the right thing to do, 25 days from leaving the White House? I mean, let's set aside Trump for a moment, he was -- not even implicitly -- he was explicitly criticizing Hillary Clinton here. What's the point of that?

ANGELA RYE, POLITICAL STRATEGIST: Well, I think the point is he was talking to his friend, as you just noted in interview with David. This is someone who, you know, he's guards down, and being completely honest. I think it's fine for him to believe that he would have had a good shot at Donald Trump.

I think his approval rating affirms that fact. I think the fact that there are 20-plus million Americans on Obamacare and have health insurance speaks volumes. I think the fact --

SCIUTTO: But, Angela, point of order, if I can, you and I know that President Obama, he's very careful with his use of words. You know, he's not a guy who tweets off the cuff often. I mean, this did not --

RYE: Never.

SCIUTTO: -- seem like an accidental message. It seemed like a very well thought out criticism of the Democratic nominee.

RYE: No. I think my point is -- I think my point is he was still speaking to his friend. I don't think he would have said it differently, necessarily, or lied under any other auspicious. I think my only point is that this is Barack Obama completely unguarded and he is almost out of the door. So, why not tell people factually what he thinks?

I think the reality of what he's saying, it may be more challenging than that. Organizing for America, that if we're honest, competed quite a bit with the DNC for resources and as a result, neither organization was completely effective. I think that that's why you have for the first time in some time a really contested DNC chair race with someone like my friend, Jamie Harrison, running saying, listen, it's time for new leadership.

[20:10:04] We have to grow a Democratic bench. The president intends to do just that when he starts this organization, this foundation on the outside. So I think it's OK for him to say, hey, I think that I would have won and beat Donald Trump. Again, I think his approval rating states the same.

SCIUTTO: Kayleigh, let me ask you, because in effect, he's saying that the party -- the party image that he projected would be successful for him and presumably for other Democratic candidates who don't make the same mistakes that Hillary Clinton made. As a Republican and Trump supporter, do you almost relish that? Do you relish the Democrats sticking with the plan, in effect?

KAYLEIGH MCENANY, CNN POLITICAL COMMENTATOR: I do relish the Democrats sticking with the plan because I think it's an awful plan and one that will ensure they'll continue losing for a very long time.

You know, the president -- President Obama has a point that he is popular, more popular than Hillary Clinton. That's for certain. So, you know, there is that. I do think he would have been a more viable contender.

But what I have a problem with, what I think a lot of Americans were very confused by when they watched this interview with David Axelrod is when President Obama said, we bleed with these communities, we feel for these communities, and he was so out of touch and tone deaf to me throughout this whole election -- take, for instance, his last press conference where he spent the first few minutes saying, "This is what I have done for you," when he stood up at that rally, his first rally with Hillary Clinton and said, "Hey, pat me on the back, thanks, Obama, your gas prices are better," or something to that effect.

When he's laying forth this optimistic view of the world he has created --

SCIUTTO: Kayleigh, don't the numbers --

(CROSSTALK)

SCIUTTO: Clearly, he's out of touch, lost the election, but unemployment's down, stock market's up from 2008, gas prices are down. I mean, by a number of economic issues -- by a number of economic measures, he can make a claim. MCENANY: But there's one economic indicator that matters and it's how

people feel. And when you have 60 percent of the electorate telling CBS in a battleground poll, "I feel the economy is rigged against me," rigged against me, those are strong words. That's how the electorate feels because the reality is poverty rates have gone up. Wages are still not past where they were pre-2007, 2008 levels.

There's a lot of hurt out there. And he underestimated that. Democrats underestimated it every single step of way.

SCIUTTO: David, I want to ask your view on that. That's a fair criticism, because in effect, to some degree, you're hearing from Obama, stick with the plan. No word for twice, with some minor adjustments, a better candidate in way, or at least better campaigning, maybe not a better candidate, we could have won the White House.

But as Kayleigh makes a very good point -- I mean, you went to these states, Michigans of the world, there were districts that swung hard from Obama to Trump. Is there a sense they're missing the writing on the wall here?

DAVID SWERDLICK, WASHINGTON POST: Well, I think Kayleigh makes a point, yes, people out there did feel disaffected. I don't think Secretary Clinton did a good job always of making the case for continuing President Obama's policies.

But where I disagree with Kayleigh is there's only one metric. Those metrics you just ticked off. Stock market is almost at 20,000. The youth reunemployment is under 5 percent. President Obama has a 56 percent approval rating.

You know, if the question is, do Democrats have problems, does President Obama have a problem not having had coattails? Yes. If the question was if he had run, could he have won? Yes, President-elect Trump.

SCIUTTO: You know, interesting, Matt, and I want to ask your view on this, Angela, as well. Speaking with David Axelrod, he made the point that there were other mistakes from his point of view, identity politics, right, in a way this coalition that -- if not ignored, it didn't pay enough attention to white working class folks. As you look at it from the outside, do you see -- I mean, are you hearing Democratic voices that hear that message, in effect?

LEWIS: No. I think that Democrats are in shock because unlike Republicans who had years of soul searching and kind of assuming they were going to lose this election, Democrats were shocked. And so, you go through the 12 stage of denial and all that stuff.

And the other thing is President Obama, by his very nature, the no- drama Obama thing, means he doesn't really ever overreact. He sort of downplays everything. I think he's downplaying this.

Democrats have a serious problem and it's hard, you know, to have a coalition. How do you satisfy Black Lives Matter and millennials and coal miners in West Virginia? You can't be all things to all people. I think the Democrats have to do that soul searching that they weren't prepared to have to do.

SCIUTTO: Angela, is that a fair criticism?

RYE: I hear Matt, but, of course, I respectfully disagree. I think here's the reality of it. We need to be careful with our words as well. We can't continue to say, or we shouldn't continue to say, white working class voters.

The fact of the matter is, whether you're living on a minimum wage and you're white, black, green or purple, you're still living on a minimum wage and can't afford to pay your bills. We need to start talking to working-class people. We need to start saying, yes, Black Lives Matter because everybody's life matters and we're not going to treat your life as any different.

However, that's not what history has told us.

[20:15:01] And until we begin to recognize what history said, we can't begin to debunk the lies of the oppressor. So, first, we have to come to terms with the fact it's not the Democrats who have an identity crisis, it's America. We have to start telling the truth. The sooner we begin to tell the truth, the sooner we can make life better in this country for all Americans.

SCIUTTO: You know, the one sort of expression, or rather, acceptance of responsibility at least in this interview was from President Obama, himself. If you look at the numbers, lost seats in the House, in the Senate, in the state governors' offices, in state legislatures. It's going to be enormously important when you have redistricting, when you have votes in 2020 with the census.

Did that strike you, David Swerdlick, that the president said, listen, here was my -- here's the mistake I made?

SWERDLICK: Yes, no, I think President Obama, if he didn't quite in this interview, needs to be more full-throated about owning some responsibility for not having those coattails other than in 2008. As Angela said a few minutes ago, the fact that he created a separate Organizing for America I do think hurt Democrats in 2010, 2014, 2016. Certainly.

At the same time, I think because, in my view, President Obama would win again were he to run, I think that a lesson that Democrats have to take you need better, more charismatic candidates who can communicate a straightforward message to other people. Donald Trump didn't win because of a specific policy. One, because he knew how to reach people out there.

SCIUTTO: Kayleigh, final thought, there is a danger on both sides of over-learning the lessons, isn't there, a very close election. Are you concerned the Republicans might say, we got to figured out, right, and perhaps overplay a mandate?

MCENANY: No, I'm not concerned about that. You know, I think there are certain policies that President-elect Trump has to deliver on if he wants to get another term. And namely that is trade. It's the Michigan voters, it's the Wisconsin voters, it's the Rust Belt voters who are so disenfranchised and feel so left out in the cold. Those are the voters that put the president-elect over the line and he must, has to deliver for those voters on trade, on taxation, and finally on Obamacare.

And I think if he delivers, then I think we have learned all the lessons we need to learn and he'll have be terms -- he'll have one more term to come and the Republicans will do well going forward.

SCIUTTO: Kayleigh, Angela, Matt, David here in Washington, thanks very much.

A lot more coming up tonight including president-elect Trump's announcement that he is dissolving his charitable foundation. And the state attorney general who says, not so fast, we're still busy investigating that foundation. That's right after this.

(COMMERCIAL BREAK)

SCIUTTO: In this season of giving, Donald Trump is giving up his charitable foundation. He says he wants to avoid even the appearance of conflict of interests with his role as president. However, critics say it goes beyond just that. The Trump Foundation, they say, has more than just an appearance problem. They say it is much less charitable than most, and perhaps is breaking the law to boot.

More on all of that now from CNN's Dana Bash.

(BEGIN VIDEOTAPE)

DANA BASH, CNN CHIEF POLITICAL CORRESPONDENT (voice-over): The president-elect's team is frantically trying to figure out what to do about his vast business interests, even Trump-owned properties like Mar-a-Lago, where he he's staying for the holidays.

But they're off to a tough start. A Christmas Eve transition announcement about shuttering the Trump charitable foundation hit a road block. The New York attorney general who was investigating the foundation's alleged violations said through a spokeswoman, "The Trump foundation is still under investigation by this office and cannot legally dissolve until that investigation is complete."

A "Washington Post" investigation reported the foundation spent $258,000 to settle legal problems unrelated to the charity, and Trump separately used charity money to a six-foot-tall portrait of himself.

A former GOP White House ethics attorney says dissolving the foundation could take time.

RICHARD PAINTER, FORMER WHITE HOUSE ETHICS ATTORNEY: You need to make sure the foundation is completely independent of your for-profit business enterprises. You cannot have self-dealing in foundations. And I don't know whether the rules were violated here or not. BASH: Regardless of the investigation, ceasing operations on the

Trump Foundation is hardly a heavy lift. Trump hasn't donated since 2008, and it has no paid staff.

The real question is how Trump will separate himself from the for- profit Trump Organization, a worldwide empire, including Trump Golf, International Realty, Trump Winery and Trump Hotels. The law does not require a president to divest himself from business interests, but potential conflicts abound. People could try to influence the president by staying at his hotels, for example.

And the most difficult hurdled could be the Emoluments Clause of the U.S. Constitution, which specifically prevents elected officials from accepting any present or money from foreign government or leaders.

PAINTER: There are a whole lot of problems that I think President Trump could deal with by selling off is business interests, or giving it over to a trustee in a blind trust, so the trustee can figure out how to dispose of these properties and he can focus on being president.

BASH: A press conference intended to detail how Trump will sort of this out was scheduled for two weeks ago, but that was delayed under January to give them more time.

(END VIDEOTAPE)

BASH: An attorney for the Trump Organization tells CNN it is continuing to re-evaluate various transactions they are involved in to take measures to comply with all conflict laws. Ethics experts say the only real ironclad way to separate the Trump administration from the Trump business is putting it in a blind trust, but the president- elect is resisting and instead sources say he's leaning toward finding a way to let his two eldest sons run the Trump Organization -- Jim.

SCIUTTO: Thanks very much, Dana. Those sons likely involved in the administration.

More now on that, the foundation and the legal difficulties facing it no matter what the president-elect plans to do next.

Joining us now is David Fahrenthold of the "Washington Post". He's done some of the best reporting on the Trump Foundation.

So, David, let's just lay it out there. No donation to the Trump Foundation by Donald Trump since 2008. That's eight years. Very wealthy man. No donation and he had no paid staff.

Was the Trump Foundation actually a charity in your reporting, what your reporting found?

DAVID FAHRENTHOLD, WASHINGTON POST: Well, (AUDIO GAP) other people give money to the Trump Foundation and Trump had given away (AUDIO GAP). The big problem was, though, that Trump (AUDIO GAP) can't take the money in your charity and use it to buy things for yourself.

As Dana described, a number of occasions that's what the New York attorney general is investigating.

[20:25:03] People I talked to at the foundation, worked with the foundation, been in the business for years, foundation was poorly run, which broke the law and (AUDIO GAP)

SCIUTTO: David, I want you to stay there. We're having a little bit of an audio problem coming through. We want to get that fixed so our viewers can hear exactly what you're saying. Please stay there.

Coming up next after this, we have much more on the Trump Foundation and also potential conflicts of interest in the Trump businesses. Please stay with us.

(COMMERCIAL BREAK)

SCIUTTO: Welcome back. Our apologies, we had some audio trouble with David Fahrenthold's video before the break. We now have him back on the phone. We can hear him very well.

So, David, just key questions I think for our audience maybe to split it up. One, the foundation, was it really a charity in your reporting, and two, what exactly the attorney general's accusing him of here.

But let's start with that. Did he donate money to this charity? Did it do good things for people who need things?

DAVID FAHRENTHOLD, REPORTER, WASHINGTON POST: So, it is technically a charity. Trump had given it money in the past. He started it, but he stopped giving it his own money as you said in 2008, and it was all other people donating to Trump Foundation which he would then give their money away.

So, it was a charity. It gave to charities. But often to charities that benefited Trump in some way. Some charity that did businesses with him, rented out his ballroom, things like that.

SCIUTTO: OK. So now let's look at what the New York attorney general is accusing him of here. What wrongdoing is the New York attorney general actually investigating with regards to the foundation?

[20:30:00] FAHRENTHOLD: Well, the basic thing, basic rule to remember here is if you run a charity, you can't take the money out of the charity and use it to buy things for yourself, and Trump appears to have violated that rule -- It's called self-dealing -- on a number of occasions.

Dana mentioned the portraits he bought it himself. She also mentioned these two instances where basically Trump's for-profit businesses got into lawsuits. And to get out of the lawsuit, they agreed -- the businesses agreed to pay off money to a charity. Instead of using his businesses, Trump used his charity to give that money. So, he basically saved, used his foundation, his charity to save his businesses of $258,000. So, I thought a lot of charity experts just said this is sort of the most brazen thing that they've ever seen somebody who's at charity. SCIUTTO: OK. Brazen is one question. Illegal is another. Attorney general is at least investigating that. If he finds legal wrongdoing, could Trump, himself, be held accountable and even short of that, should we expect to see him being deposed for this, taken to court? What should we expect to the next steps?

FAHRENTHOLD: Well, these are violations of the law, but it's not generally the kind of violation that would get you criminally charged. Instead, what's likely to happen is there will be some sort of settlement in which Trump -- the Trump Foundation who admit to having broken the law and Trump, himself, may be forced to pay some penalty taxes for having managed the foundation poorly. But this is not the kind of thing, I don't think, that would produce some kind of criminal charge.

SCIUTTO: David Fahrenthold, thanks very much for your patient on this. We're glad to have you on.

FAHRENTHOLD: Thank you.

SCIUTTO: Now on a New Testament holiday, some distinctly Old Testament action from Israel and, of course, a tweet from Donald Trump. Both come in response to Friday's U.N. Security Council vote in which the United States crucially abstained permitting the passage of a measure condemning Israel's West Bank settlements.

Late today the president-elect tweeted, "The United Nations has such great potential but right now it is just a club for people to get together, talk and have a good time. So sad!" As for the Israelis, they did more than tweet.

CNN's Elise Labott reports.

(BEGIN VIDEO CLIP)

ELISE LABOTT GLOBAL AFFAIR CORRESPONDENT: Israel's Prime Minister Benjamin Netanyahu is escalating his attack against the Obama administration, clearly still angry over the U.N. vote declaring Israeli's settlements illegal.

BENJAMIN NETANYAHU, ISRAEL'S PRIME MINISTER: Friends don't take friends to the Security Council.

LABOTT: Netanyahu summoned the U.S. Ambassador and has accused President Obama and Secretary of State John Kerry of orchestrating what he called a shameful ambush at the U.N. telling his cabinet he has ironclad proof.

NETANYAHU (through translator): From the information that we have, we have no doubt that the Obama administration initiated it, stood behind it, coordinated on the wording and demanded that it be passed.

LABOTT: The White House denies that, calling the claim absurd.

BEN RHODES, DEPUTY NATIONAL SECURITY FOR STRATEGIC COMMUNICATIONS: We did not draft it. We did not put it forward. LABOTT: The Obama administration maintains the U.N. vote was a last resort, after struggling for the past eight years to convince Israel to halt settlement construction on occupied lands the Palestinians claim for their state.

RHODES: For years, we've seen an acceleration in the growth of these settlements. And frankly, if these current trends continue, the two- state solution is going to be impossible.

LABOTT: Officials are now worried with U.N. backing Palestinians will push for sanctions, boycotts and take Israeli soldiers to the International Criminal Court.

RON DERMER, AMBASSADOR OF ISRAEL TO THE UNITED STATES: What this resolution just did is it gave the Palestinians ammunition in their diplomatic and legal war against Israel, and the United States not only didn't stop it, they were behind it.

LABOTT: Netanyahu is now putting his hopes in president-elect Donald Trump and members of congress who are promising to defend the U.N. unless the vote is overturned, hoping that will give Trump leverage.

NETANYAHU: I look forward to working with those friends and with the new administration when it takes office next month.

(END VIDEO CLIP)

SCIUTTO: Elise Labott joining us now. So, Elise of course, president-elect Donald Trump's tweet about the U.N. today comes on the heels of his angry tweets as well about this U.N. resolution where abstained by the U.S.

LABOTT: That's all right. And basically, when if first came out, he condemned it and said, you know, there's a new sheriff in town on January 20th, things are going to be different. Over the weekend he got, you know, slightly more somber and serious about it and tweeted that, saying "the vote will make it much harder to negotiate peace. Too bad, we will get it done, anyway."

And I have to tell you, Jim, it's not just the Israelis that are hoping that president-elect Trump when he comes into office will be work on the Mideast peace process, despite the fact that Donald Trump has promised to move the U.S. embassy to Jerusalem. Despite the fact he appointed a very controversial hardline ambassador who supports settlements and ...

SCIUTTO: It is against the two-state --

LABOTT: And it's against the two-state solution. The Palestinians say they are hopeful that Donald Trump with his unorthodox approach may be and they hope he will be the U.S. president to finally make that deal and, well, the old administration, the one that's leaving on January 20th, is going to be laying out its vision for what it wasn't able to accomplish. We understand Secretary of State John Kerry is going to lay out the administration's approach, how they see a Mideast peace process maybe later this week, and it's really interesting how, you know, Secretary Kerry worked so hard on this, now is handing it over to president-elect Trump.

[20:35:13] SCIUTTO: It'll be Interesting to see Israel and also Trump's reaction of course to John Kerry's speech when it happens.

Elise Labott, thank very much.

Joining us now, we have "Atlantic" Contributor and CNN Political Commentator, Peter Beinart, also CNN's Senior Political Analyst, David Gergen who's been in the room at some of the key moments between American presidents and their Israeli counterparts.

So, David, if I could start with you here, how big a deal is this? Is this, first the resolution, and now Donald Trump in effect, you got Trump versus Obama with 25 days to go on a major Mideast policy issue.

DAVID GERGEN, CNN SENIOR POLITICAL ANALYST: It's a much bigger deal than anybody would have expected, Jim. And nobody, I think, saw this coming and for the U.S. to reverse a longstanding policy, a vetoing resolutions like this, and protecting the Israelis from some of the, you know, the U.N. has often been a hotbed from Israeli point of view of anti-Semitism, anti-Israeli feeling and the U.S. has always protected them.

When the president did this at the last minute just before leaving office, it threw a hand grenade into the middle of things. And I don't know where this is going to go. I -- it doesn't mean -- they might well have left some of this alone because there are bigger issues right now in the Middle East that are demanding attention as you well know. How are you going to carry on the war against ISIS, how are you going to work with the Syrians. What are you really going to do about Iran and the expansion of its efforts?

I think this is going to complicate those -- the pursuit of those priorities and there is a danger, I must say, that I think the Trump forces will overreact in order to prove how pro-Israeli they are, move immediately to move the capital and recognize Jerusalem as the capital, that would really as you will know, it cause explosions all across the Middle East.

SCIUTTO: Peter, you've been extremely critical of Israel's settlement policy. How do you view this? Do you think there is any value in calling out Israel on a public stage for an issue that, frankly, Republican and Democratic administrations have criticized, the policy the Republican and Democratic presidents have both criticized.

PETER BEINART, CONTRIBUTOR, THE ATLANTIC: Yeah, and first I would just say I have to disagree with a little bit with my friend, David. I don't think this is as much of a break as he suggests. In fact, every American president going back to Ronald Reagan has allowed U.N. resolutions to pass that Israel did not want. Ronald Reagan actually voted, not just abstained, but voted for a resolution condemning Israel when it attacked the Osirak reactor and withheld weapons sales. Reagan allowed repeated resolutions to go through that criticized Israel on settlements. George W. Bush allowed a resolution the Israelis were bitterly opposed to calling for a Gaza cease-fire in 2009. I think the larger context here is that Barack Obama believes that the two-state solution is dying. And many of Israel's own leaders believe it's dying.

We now have two former Israeli Prime Ministers, Ehud Olmert and Ehud Barak and two former top Security Officials, (inaudible) who have said that Israel is on its way to being an apartheid state.

(Crosstalk)

SCIUTTO: Trump's choice for Israeli ambassador has said ...

BEINART: James -- James -- right, James Mattis, in fact, also, talked, because you remember, Israel, in the West Bank, Israel controls millions of Palestinians who don't have the right to vote, live under military law, and are not citizens. If that's a permanent condition, it raises very serious questions about Israeli democracy and many top Israelis, not Netanyahu, but others have said that. I don't think Obama thinks he can change it, but I think with an eye to his legacy, he wants to be on the record of at least having tried to put down some kind of marker to saying, I did not acquiesce to this.

SCIUTTO: David, I want to ask you because you worked in a number of administrations from both parties through some severe crises. That you often hear what Donald Trump since the election, you know, on Taiwan policy -- on Russia policy, here on the Middle East that, well, they'll shake it up, two former top Security Officials and maybe that will work. It's been so intractable.

In your experience, does that work in the field of international affairs, in the field of some of the biggest national security challenges this country, and our allies and adversaries face?

GERGEN: I just think we've never faced, brought in a president who is as unpredictable and volatile and impulsive as Donald Trump. I don't know how it's going to work out. I don't think anybody does. I must say the presidents who've been most successful in international affairs are those who have a strategic sense, a broad sense of where they're trying to go, what they're trying -- what their priorities are and they stick to them and pursue them pretty relentlessly and that seems to work.

You know, we won the Cold War in effect because we had a series of administrations who embraced the same strategy of containment toward the Soviet Union. Ultimately that paid off and I don't see that here, and that's why I have this fear, I think Peter was right on a lot of things he said, by the way.

[20:40:04] But I do have this fear, Peter, that Donald Trump is going to be tempted now to go further over to prove his faithfulness to the Israelis and make it much more difficult to get back to a two-state solution process which I do think is dying and needs to be pursued.

SCIUTTO: Final thought from you, Peter. Do you think that's a real danger, a backlash, in effect? BEINART: Well, look, so, even before Obama did this, Trump had already appointed David Friedman who's kind of explicitly against the two-state solution and explicit settlement advocate.

Look, this game is moving outside of America. What's going to happen is for better or worse, there's going to be increasing mounting pressure on Israel from Europe and from other parts of the world to try to respond to the fact that Israel is creating a permanent one- state reality. And it's important to remember that when Israel builds settlements, it's not like this is unoccupied land. A lot of these settlements are built on privately-owned Palestinian land but the land is taken from Palestinians because they lack basic rights as non- citizens. This is a serious human rights problem and I think it's just --.

GERGEN: But Peter, there is one thing, I think --.

SCIUTTO: Final thought, David, because we're all going have to leave it.

GERGEN: You've got the western wall in here in this resolution as being it.

BEINART: No, but David --

GERGEN: That was definitely held by the Israelis. You can't go forward with negotiated politics ...

BEINART: Nobody thinks, David. There's been never and never -- there's been never any negotiation which has contemplated the idea that Israel would not have sovereignty over the western wall. That's not the discussion. The discussion is, is there going to be a viable Palestinian state, or not when Israel massively subsidizes, pays Israelis to move into the west bank?

SCIUTTO: Gentlemen, that right there is an encapsulation of the difficulty of this issue. Peter Beinart, David Gergen, our conversation will continue, no question.

Just ahead, we'll take you to coal country and talk to people who voted for Donald Trump on the promise of more jobs even though the outcome now leaves their health and finances actually more uncertain than ever, how mining families reconcile casting votes? It could come back to actually hurt them. That's next on A.C. 360.

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[20:45:38] SCIUTTO: When President-elect Trump takes the oath of office, the clock starts running on campaign promises including bringing back jobs to coal country and repealing Obamacare, that won him the support of many coal miners, yet now they're worried their votes will end up hurting both their health and their finances.

CNN's Miguel Marquez has this report.

(BEGIN VIDEO CLIP) MIGUEL MARQUEZ, CNN CORRESPODENT: The coal-laden hills of eastern Kentucky --

DONALD TRUMP, PRESIDENT-ELECT USA: We're going to bring the coal industry back.

MARQUEZ: -- Trump country. Neil Yonts, a Democrat and coal miner for 35 years, initially supported Hillary Clinton. But --

NEIL YONTS, FORMER COAL MINER: I voted for Trump. Maybe a mistake, but I heard him say he'd bring coal back.

MARQUEZ: A mistake, maybe, because Yonts now suffers from black lung disease.

YONTS: From there to here, you see depths in my breathing. I need that closed.

MARQUEZ: He voted for Trump to bring jobs back but now fears Trump's promise to kill Obamacare will also end his black lung benefits.

YONTS: When they eliminate the Obamacare, they may just eliminate all the black lung programs. It may all be gone. It don't matter how many years you got.

MARQUEZ: Three sentences in the Affordable Care Act made it easier for victims of black lung to get monthly federal benefits, if they worked 15 years or more in the mines. And if they died, the benefits automatically extended to their widows.

PATTY AMBURGEY, MINER'S WIDOW: I will be withdrawing $643 and I think $0.42.

MARQUEZ: Once a month?

AMBURGEY: Once a month.

MARQUEZ: Patty Amburgey just got her first payment, her husband Crawford, after 32 years in the mines died in 2007.

AMBURGEY: To say it end with somebody you lived with 45 years, you know, from my (inaudible) man to a child, is very hard.

MARQUEZ: Getting the payment can also be difficult even with the law, it took her three years. Now, her black lung widow benefit along with social security and a tiny $62 a month pension keeps her financially afloat.

So this money is important to you?

AMBURGEY: Absolutely, absolutely. It's not a large amount, but it's enough to pay the bills.

MARQUEZ: Keeping up with the bills here for many, a lifetime struggle. So Trump's full-throated promise of jobs was a powerful message. The unemployment rate in Leicester County, 10.3 percent, more than twice the national leverage.

STEPHEN SANDERS, DIRECTOR APPALACHIAN CITIZENS' LAW CENTER: This area has seen a terrific decline in the number of coal mining jobs in the last five years and those jobs tended to be high-paying jobs.

MARQUEZ: Stephen Sanders represents miners applying for black lung benefits. As jobs have evaporated, he says, Obamacare benefit is more important than ever.

SANDERS: President-Elect Trump promised people that he was going to restore mining jobs. I don't think he thought about what the Affordable Care Act might mean to miners who are applying for black lung benefits.

MARQUEZ: Linda Adams' husband, Tony, died three years ago. She's now applying for black lung widow benefits.

You supported Donald Trump from this election?

LINDA ADAMS, MINER'S WIDOW: I did. I did.

MARQUEZ: But if Obamacare goes away?

ADAMS: If Obamacare goes away, I'm going to be in a world of depression.

MARQUEZ: Today, Adams devotes her life to helping others apply for benefits, she hopes will survive even if Obamacare is abolished, her enormous expectations now squarely on President Trump.

ADAMS: If he don't come across like he promised, he's not going to be their next time, not if I can help it.

MARQUEZ: Trump's future opposition already taking shape if jobs don't return and Obamacare benefits vanish.

Miguel Marquez, CNN, Whitesburg, Kentucky.

(END VIDEO CLIP)

SCIUTTO: When we come back, we're going to do our best tonight to highlight the joy that singer George Michael brought to the world, even as we mark his untimely passing on Christmas Day. That's next.

(COMMERCIAL BREAK)

[20:52:51] SCIUTTO: Tonight, fans are mourning the passing of British pop star, George Michael, who died on Christmas day at his home in England. Apparently, his manager says, from heart failure, his death, though, unexpected. He was just 53 years old. More now from CNN's George Howell.

(BEGIN VIDEO CLIP)

GEORGE HOWELL, CNN NEWS CORRESPONDENT: It's the song that had the world dancing, that hit, "Wake Me Up Before You Go Go." It was 1984 and they were the British duo known as "Wham". They had several top 10 hits together, but really, it was George Michael with that statement T-shirt, those moves that quickly took the spotlight, sealing his fame with this chart-topping song, "Careless Whisper".

Michael split from bandmate Andrew Ridgeley in 1986 and launched his own solo career, never looking back, but headed straight into his first big culture clash.

The year was 1987, George Michael looking the confident rock star in a provocative video with an equally provocative title. The legendary Casey Kasem refused to even say the title of the song on his American top 40 radio show and some pop radio stations wouldn't even play the song until after dark.

Michael's lyrics bumped heads with not just conservative who thought he'd gone too far, but with a Hollywood desperate to bring attention to the AIDS epidemic and the need for safe sex. Michael would later say his lyrics were misunderstood.

By the late 1980s, George Michael was a bonafide superstar, garnering awards, hanging out with celebrities and royalty, and delivering more hits, like "Father Figure" and "One More Try".

[20:55:00] In the 1980s, George Michael saw the height of his success. It can be said the 1990s weren't quite as kind. Fewer smash hits and then this. April 7th, 1998, Michael was arrested by an undercover male police officer charged with engaging in a lewd act in a park in Beverly Hills, California.

It took no time for his arrest to become an international headline. On CNN, not long after the arrest, Michael confirmed what had long been rumored. He was gay.

GEORGE MICHAEL, BRITISH POP STAR: And I want people to know that I have not been exposed as a gay man in any way that I feel. I don't feel any shame for -- I feel stupid and I feel reckless and weak for having allowed my sexuality to be exposed this way but I don't feel any shame whatsoever and neither do I think I should.

HOWELL: In the years to come, there were more scuffles with the law, drug-related arrests and a nasty car accident in 2010. Michael was found to be driving under the influence of cannabis and went to jail.

In 2011, he fell ill with a severe case of pneumonia and had to cancel his European tour. But there was always the music.

George Michael once said, "I still believe that music is one of the greatest gifts that God gave to man." Lucky for us, he left us plenty of it.

(COMMERCIAL BREAK)

[21:00:09] SCIUTTO: Thanks very much for watching. I'm Jim Sciutto, the CNN's "Special Report", the legacy of Barack Obama starts now.