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THE LEAD WITH JAKE TAPPER

Red Sox Legend Considering Senate Run in 2018; U.S. Sailor Killed in Action in Iraq Identified; Clinton: Russia Trying To Tip Election For Trump; Clinton: Russia, WikiLeaks Working Together; Trump: Putin Outsmarted Clinton, Obama; Obama: Trump, Putin Have "Bromance"; Russian Democracy Activist Weighs In On 2016 Race; Little Time Left to Hear Clinton, Trump Debt Plans; Clinton: I Will Not Add A Penny To Debt; Trump: We Are Going To Cut Taxes Massively. Aired 4:30- 5p ET

Aired October 21, 2016 - 16:30   ET

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


CURT SCHILLING, 3-TIME WORLD SERIES CHAMPION: Well, I'll tell you, Jake, honestly like in lot of places I don't think the politics much the populace in Massachusetts. I think in conversing and being involved in this state, being around, I think the state is much more moderate than politicians and media would have people believe.

[16:30:10] But at the end of the day, yes, I'm going to have to convince people that might otherwise vote blue to vote not blue. I'm a registered independent. You know, whether I -- I'm not sure how that would play, I probably would switch to the Republican Party, even though I'm as fed up with the right as I am with the left now. But again, yes, I'm going to have to convince people and if I can't, I don't win.

JAKE TAPPER, CNN ANCHOR: So if you were to run, obviously, one of the issues that would be brought up by your opponents would be the fact you were let go of ESPN after sharing a meme on Facebook, a man dressed as a woman, the caption, quote, "let him in the restroom with your daughter, or else, you're a narrow minded, judgmental, unloving, racist bigot who needs to die." You're going to have to defend that post to a lot of progressive voters.

You're also going to have to depend retweeting an image that likened 5 to 10 percent of Muslims worldwide, which computes to about 80 million Muslims to Nazis.

Are those --

SCHILLING: No, no, no, that's not true.

TAPPER: No?

SCHILLING: That's not true. No, I compared five -- I compared Muslim extremists to Nazis. That extremist part is -- I know it's tricky, but that's the part that gets left out by everybody.

That was -- if you take the word extremist out, that's an incredibly racist post, which is why the word extremist is in there. You could argue -- and listen, after been multiple stories about the comparison. There's a very long standing connection between Islam and the Nazi Party, and you can go back to before the Second World War and talk to that.

And as far as the trans gender post, the only thing I'm going to defend in that is what I said. It wasn't my post. I was reposting a post and I have commented on it. My comment was, "Men should men's room and women use the women's room. Why do we need the federal government telling us otherwise?"

TAPPER: The last question I have for you, sir, is -- has to do with Donald Trump, because if you do run, you'll be -- I'm sure the Democrats will try to tie Donald Trump to you and make you the Massachusetts version of Donald Trump. You've not only endorsed Donald Trump back in May, but you wrote at the time on your blog that Trump's commentary on women was uncomfortable. Since then we've seen the tape emerge of Mr. Trump seemingly bragging about what sounds a lot like sexual assault.

In you initial response on Twitter, you seemed to dismiss the lewd video saying it was Mr. Trump talking big, that's your term. Is that all it is to you, that it's just him talking big?

SCHILLING: Well, listen, Jake, you graduated from Dartmouth. You're a pretty smart guy and I would argue as a moderate, as a conservative, one of the few people left in the media that tries to go, straddle, be fair and objective. I'm curious as to why we spend seven or eight news cycles talking about disgustingly crass, inappropriate sexist comments he made ten years ago over the fact that every single day, WikiLeaks is showing us that Hillary Clinton is exactly the criminal we thought she was.

And when you look at that, no one condones what he said. But when you take the liberal perspective of my comments, they go from me not condemning the comments to me advocating for child molestation and pedophilia. It's that jump. And people are smarter than that, but that's the argument they go to.

I'm going to -- I would like to ask you this question, honestly, Jake.

TAPPER: Sure.

SCHILLING: As someone who is going to be -- I'm assuming you will vote for Hillary Clinton.

TAPPER: No.

SCHILLING: OK, I'm assuming you're not going to vote for Donald Trump.

TAPPER: I don't vote in presidential races.

SCHILLING: OK. I would like to ask you something as a person who is practicing the Jewish faith and has since you were young, I don't understand, maybe this is amateur, non-politician in me, I don't understand how people of Jewish faith can back the Democratic Party which over the last 50 years have been so clearly anti-Israel, so clearly anti-Jewish Israel, that I don't know what else would be done, said, or happen for people to understand that they don't -- they're not -- the Democratic Party is allied with Israel only because we have agreements in place that make them have to be.

TAPPER: Well, I don't speak for Jews, and I don't support the Democratic Party or the Republican Party. I would imagine, just to try to answer your question, that one of the reasons many Jews are Democrats s more to do for social welfare programs and that sort of thing --

SCHILLING: That's fair.

TAPPER: -- than it does for Israel, and I know that a lot of Jews who are strong supporters of Israel do support the Republican Party.

SCHILLING: Right.

TAPPER: But again, I don't speak for Jews.

SCHILLING: Right, no, I know you don't. I just always find it a great conversation for somebody of your faith to -- because I want to understand the reason behind some of those things.

[16:35:07] So I appreciate that.

TAPPER: All right. Well, we can keep in touch and we can have more conversations and hope you'll come back. Thank you so much, Curt Schilling.

SCHILLING: I will, Jake. Thank you very much.

(END VIDEOTAPE)

TAPPER: ISIS fighting back as the retake Mosul from the terrorist group. ISIS takes aim at another key Iraqi city. That story next.

(COMMERCIAL BREAK)

TAPPER: Breaking news in our world lead, we are learning more about the U.S. service member who was killed in a roadside bomb attack in Northern Iraq. This was the first U.S. combat death since the operation begun to retake Mosul, once Iraq's second largest city.

Let's bring CNN Pentagon correspondent Barbara Starr.

And, Barbara, what can you tell us about the fallen soldier? What do we know?

BARBARA STARR, CNN PENTAGON CORRESPONDENT: Well, Jake, a short time ago, the Pentagon announced that this was Navy Chief Petty Officer Jason Finan of Anaheim, California, making that official announcement of his identity.

[16:40:08] The latest, the fourth American to be killed in Iraq, in action against ISIS, the first combat death since the operations, the very dangerous operations near Mosul began. (BEGIN VIDEOTAPE)

STARR (voice-over): Gunfire erupted on the streets of the Iraqi city of Kirkuk after ISIS militant launched a surprised attack. Video captured the terrorists entering at night, ongoing clashes reported. ISIS's sudden attack into Kirkuk some 100 miles southeast of Mosul is seen by U.S. military officials as an ISIS attempt to divert Iraqi forces from the larger fight to retake Mosul.

Kirkuk is a city of strategic significance because of its large oil reserves.

LT. GEN. STEPHEN TOWNSEND, COMMANDER, COMBINED JOINT TASK FORCE, OPERATION INHERENT RESOLVE: They are a very resilient and challenging folk. They are very adaptable, very creative, cunning.

STARR: The first U.S. service member to be killed in the Mosul operation died after his vehicle hit an IED.

Up to 200 U.S. troops are in and around Mosul, advising Iraqi and Kurdish forces.

They are confronting initial rings of bombs and booby traps outside the city. ISIS posting new video of clashes, it's weapons defenses are even greater inside Mosul. U.S. officials say the top U.S. commander telling the BBC, ISIS must be stopped.

TOWNSEND: They saw people's head off on TV. They drown people on video it. They burn people alive in cages. They crucify people. And then they drive over people on the street with bulldozers.

Are they using human shields in there? Yes, they're probably using human shields in there.

STARR: The U.S. believes some ISIS leaders have already escaped Mosul. Remaining are about 3,000 to 4,000 fighters, about 1,000 are hard core foreign fighters in a city of 1 million.

The U.S. is trying to get a better fix on the strength of the dissident movement inside the city, and whether those foreign fighters inside Mosul will fight to the death.

(END VIDEOTAPE)

STARR: U.S. officials believe ISIS is already making plans for what comes next, that they will plan to become an insurgency, meld back into the civilian population and stage attacks from there -- Jake.

TAPPER: All right. Barbara Starr, thank you so much. Appreciate it.

It's not a new Cold War, but it could end up being even more dangerous, and it's the next president's problem. What is Vladimir Putin up to and how can the U.S. keep him in check? Chess legend, Putin critic and political activist Gary Kasparov will weigh in next.

(COMMERCIAL BREAK) [16:45:00] HILLARY CLINTON, DEMOCRATIC PRESIDENTIAL CANDIDATE: But Donald really is as healthy as a horse, you know, the one Vladimir Putin rides around on.

JAKE TAPPER, CNN THE LEAD ANCHOR: Welcome back to THE LEAD. I'm Jakes Tapper. That was Hillary Clinton mocking Donald Trump for his bromance as President Obama describes it with Russian President Vladimir Putin. The jokes come amid serious charges that Moscow is currently trying to tip the election for the GOP nominee. The White House has publically blamed Russia for hacking and stealing e-mails from the Democratic National Committee and from Clinton campaign chair John Podesta, and then allegedly releasing them to the public via WikiLeaks, not to mention, of course, breaches into state voter registration systems across the U.S.

Joining me now is chess legend, Russian political activist Garry Kasparov, a fierce Putin critic who fled Russia back in 2013. He's out with a new book titled, Winter is Coming: Why Vladimir Putin and the Enemies of the Free World Must be Stopped. Gary, good to see you again. Thanks so much for stopping by.

GARRY KASPAROV, CHESS LEGEND AND RUSSIAN POLITICAL ACTIVIST: Thanks for inviting me.

TAPPER: So, the Clinton campaign has accused WikiLeaks of colluding with Russia to release embarrassing campaign e-mails and sway the U.S. election. WikiLeaks denies it. But however WikiLeaks got the e- mails, do you agree with the premise that the White House puts forward that Russia is trying to help elect Donald Trump?

KASPAROV: Absolutely. Putting hackles for WikiLeaks have released tons of e-mails from Hillary Clinton and DNC, and nothing from Donald Trump and GOP. I don't believe for a second that Trump was clean and they couldn't find anything, more likely they had plenty, but they decided to use it privately to good effect. So, whether we're talking about debts or blackmail, but what do we see, time and again, that Donald Trump keeps protecting Putin, keeps pushing Putin's agenda, even when it clearly hurts him politically.

TAPPER: Well, what Donald Trump says, just to play devil's advocate here, is wouldn't it be great for the U.S. and Russia to have a better relationship, so that they can cooperate these two governments on matters such as defeating ISIS, what do you think about that argument?

KASPAROV: By the way, we are seeing now that while Americans and Iraqis and Kurds are trying to take over Mosul from ISIS, Putin keeps destroying Aleppo where ISIS had no presence. And also, you know, before talking about building relations with American enemies, U.S. President must improve relations with American allies, and Donald Trump repeatedly said that, you know, he had no faith in NATO, and he was not looking for any means and ways of improving relations with American allies.

TAPPER: You say that there are a lot of parallels between Donald Trump and Vladimir Putin, what do you mean? [16:49:51] KASPAROV: Oh, I think Putin sees in Trump an ideal counterpart for his clandestine (INAUDIBLE) agenda. Trump shows no respect for democracy, for rule of law and the fact that he also now repeatedly said that elections rigged, and he would not recognize the results of the elections, it also plays into Putin's hands, because Putin's goal is, of course, to have, you know, someone like Trump in Oval Office, but it seems now out of his reach. So, Putin probably has even a bigger goal to see doubts in America and in the world about U.S. elections, about the integrity of U.S. elections. And by doing so, he can have the biggest (INAUDIBLE) political victory that KGB colonel could ever dream of, because if American elections is rigged, who cares about elections in Russia and every dictator and (INAUDIBLE) in the world will applaud Putin's efforts since they could say that elections in democratic countries, namely United States or the leader of the free world is as bad as elsewhere.

TAPPER: There was an upend by the former acting director of the CIA, Michael Morell, in which he suggested that Donald Trump was an unwitting dupe of Vladimir Putin that Putin had figured out a way to flatter Trump, and to get him to do what he wanted him to do. Do you buy that argument?

KASPAROV: I think - I think it's something more than simple flattering, because Trump, you know, even not being a very, you know, smart politician, I mean, he should recognize the damage done by his repeated statements about Putin, but he keeps doing that, so that's why I think, you know, we should look for more sinister reasons for Trump - for Trump being so pro-Putin. And again, you know, just in - the fact is that Trump's, you know, main line now is about rigged elections, you know, tells me that he has been working on fertilizing the ground for potential civil unrest. That's Putin's greatest dream, because if America after elections is draft into kind of civil unrest and the country is divided, so America will not be able to play the role worldwide, protecting the -- protecting freedom and human rights.

TAPPER: You say that Hillary Clinton is the lesser of two evils in this race, and we should point out that when she started as Secretary of State, you were critical of Hillary Clinton's Russian reset. You called it a, quote, "disaster." If she's elected president, what type of posture would you like her to take with Russia and with Putin?

KASPAROV: Oh, it's natural, you know, from what we're seeing now, Obama's, Clinton's policy toward Russia was a disaster, but from what we know Hillary always had a more hoggish on Russian (INAUDIBLE) than President Obama. And also, I mean, she's intelligent enough to learn from these mistakes, and it's quite clear for what she has been saying throughout this campaign, the last stage of this campaign, that she fully recognizes the threat that Putin causes now not only to the United States and to the - to the upcoming elections, but to the - to the rest of the world, so I hope that her administration will realize that only United States can lead a coalition to stop Vladimir Putin's dangerous plans.

TAPPER: The U.N. Ambassador for Russia said that the relationship between the U.S. and Russia is worst it's been in more than 40 years. What do you think the end game for Putin is here? He doesn't want a military confrontation with the U.S., does he?

KASPAROV: Vladimir Putin will grab to everything to stay in power. His only agenda is to survive politically at home and he made actually not yesterday, not even last year, for many years he has turned Russian aggressive foreign policy as a staple of his domestic propaganda. If you - if you have a chance to listening to Russian televisions, it's 24/7 anti-American paranoia, and at one point, have to back up your words with some actions. So, that's why do not be surprised that while America is being, you know, engaged in this post- election debates, hopefully there's no civil unrest will be result of that. Putin can take some decided steps in, say, in the Baltics, because confrontation with the United States and the free world is the only way Putin can justify his endless rule in Russia.

TAPPER: That's chilling. Gary Kasparov, thank you so much. Appreciate it, Sir.

KASPAROV: Thanks for inviting me.

TAPPER: Some of the most popular websites in the world not functioning today, because of an internet attack. Now, federal officials are investigating who might be behind it? Who is it? That story ahead.

(COMMERCIAL BREAK)

[16:55:00] TAPPER: Welcome back to THE LEAD. We're now down to 18 days until Election Day. It's a number we've all memorized here. Time is winding down for the candidates to offer any more specifics on how they might slash the nation's $19 trillion national debt. And that's the subject of this week's installment of America's Debt & The Economy. Tuesday's final debate was the last time Hillary Clinton and Donald Trump had an audience of millions to offer details. Here's how Clinton tried to sell her plan.

(BEGIN VIDEO CLIP)

CLINTON: I have said repeatedly throughout this campaign, I will not raise taxes on anyone making $250,000 or less. I also will not add a penny to the debt.

(END VIDEO CLIP)

TAPPER: A reality check, analysts say that's not entirely true. Yes, her tax plan would not tack onto the debt, but she didn't mention her spending programs. And when analysts factored that in, Clinton's plan could add $200 billion to the national debt, not all at once, that would be over a 10-year period. Now, let's turn to her rival. Here's what Donald Trump told voters at that final debate.

(BEGIN VIDEO CLIP)

DONALD TRUMP, REPUBLICAN PRESIDENTIAL CANDIDATE: We're going to cut taxes massively, we're going to cut business taxes massively. They're going to start hiring people, we're going to bring the the two and a half trillion dollars offshore back into the country, we are going to start the engine rolling again.

(END VIDEO CLIP)

TAPPER: Analysts did the math, Trump's plan could add more than $5 trillion to the federal debt according to the Committee for a Responsible Federal Budget. Trump says more jobs and the added revenue will help even out the numbers. Analysts are skeptical. Be sure to watch this Sunday at 9 a.m Eastern for State of the Union. That's it for THE LEAD. I'm Jake Tapper, turning you over now to Wolf Blitzer in "THE SITUATION ROOM." See you Sunday morning.