announcer: from our studios in new york city, this is "charlie rose." charlie: we begin this evening with the iran nuclear deal. president obama made his case for it this morning as congress prepares to vote on the resolution by september 17. the president made his case at american university where jfk delivered a speech on nuclear diplomacy in 1963. president obama argued that failure to approve the deal would be a historic mistake. he presented it as a choice between war and diplomacy. president obama: i've had to make a lot of tough calls as president.

whether or not this deal is good for american security is not one of those calls. it is not even close. without this deal, the scenarios that critics warn about happening in 15 years could happen six months from now. by killing this deal, congress would not merely pave iran's path towards a bomb, it would accelerate it. what is more likely to happen if congress were to reject this deal is that iran would end up with some form of sanctions relief without having to accept any of the constraints or inspections required by this deal. so in that sense, the critics are right. walk away from this agreement and you will get a better deal for iran. let's not mince words. the choice we face is ultimately between diplomacy or some form of war. maybe not tomorrow, maybe not three months from now, but soon.

john f. kennedy cautioned here more than 50 years ago at this university that the pursuit of peace is not as dramatic as the pursuit of war. but, it is so very important. it is surely the pursuit of peace that is most needed in this world so full of strife. charlie: joining me now is richard haass, the president of the council on foreign relations. chemi shalev, the u.s. editor and correspondent for the daily israeli newspaper "haaretz." jonathan alter, columnist for the "daily beast" and analyst for msnbc. and mark dubowitz, executive director of the foundation for defense of democracies. i'm pleased to have all of them here to talk about this vital question. the president of the united states said today at american university it is the most consequential foreign-policy debate since the decision to go

to war in iraq. the decision made in bush 43's administration, not the one you served. richard: i served both. charlie: yes. was it -- you were at the state department when the decision to go to war in iraq the second time. is this the most consequential debate in american foreign policy since the decision to go to war and why? richard: it is certainly high on the list. you can argue the decision not to get involved in syria was quite consequential. you could argue that some of the decisions on trade agreements are extraordinarily consequential, but yes. this is high, both in the specifics given the iran nuclear issue, given how already turbulent the middle east is and the fact that the united states has put a lot of credibility on the line so the stakes now transcend the regional. there is also the issue of american reliability and predictability. so, yes, this is a high-stakes issue, for sure. charlie: the most consequential debate for america, do you think? chemi: it is certainly one of the most consequential debates

for america and certainly one of the most consequential events in the history of the relationship between israel and the united states. i think it was accentuated today by the speech which was unprecedented in its singling out of israel in such an important forum for being the only rejectionist country in the world and for attacking the prime minister, both directly and by implication. i don't think we have seen anything like that ever before. it will be a bracing speech for israelis and for a lot of people who belong or are connected to the jewish establishment. charlie: they would take offense at it? chemi: they will take offense at some of it, yes. president obama -- if i can talk a minute about american jews -- he sort of touched on raw nerves that american jews have.

he spoke about the lobbyists the tens of millions of dollars, which reminded people of president bush's famous -- first bush -- famous press conference in which he spoke as himself as a tiny little man standing up against thousands of lobbyists over the hill which is one of the more uncomfortable events in jewish relations with the administration. he said he does not think he should act because it creates friction with a good ally of america which reminds people of what president reagan said that foreign countries should not be dictating the policies, the foreign policy of the united states. charlie: he was right. chemi: i'm sure he was right. nonetheless, there is a difference between knowing something and saying something. and, i think it was a bit -- it was tougher than what people, in israel at least and in the jewish community, expected. charlie: but, a lot of people take offense in america at the efforts of the israeli prime minister to come here and lobby congress the way he did and

speak against the president the way he did which seems to me more dramatic than a speech at american university. chemi: there are a lot of people in israel who criticized the way the prime minister is handling this. my newspaper has an interview with the president of israel which will be published on friday in which he criticizes the way the prime minister is handling relations with the united states, especially on the issue of iran. he thinks that the prime minister should show more restraint, but one does not negate the other. you could be critical of the prime minister and still be offended by the tone of the president. charlie: by both, you are saying. you have an idea that the prime minister would be better served if had come over and made the points he believes in and let's have a dialogue here rather than going full force against the president. richard: if it is a stark choice of yes or no, it does not give you a lot of chance to influence things. essentially, it is a black or white decision. i testified earlier this week before the senate armed services

committee and where i think the united states would come out would be somewhere in between. if there is a decision to go ahead with the agreement, they will have to be added to it, either formally or informally, a set of conditions. what would be intolerable that iran would do now in terms of noncompliance? what would be intolerable in 10 or 15 years in terms of their nuclear arsenal? what we would do in order to reassure israel, the saudis and others in the meantime. in the case of the saudis or the uae, they are not tempted to go ahead and have nuclear programs of their own. charlie: so what happens to the agreement if we put all these conditions to it? do the iranians have to agree to it? richard: no, this would be unilateral american statements. they would not necessarily be amendments to the treaty. what i'm thinking about is either a white house statement or some companion legislation, or a joint resolution that would make it clear how the united states plans to address what i would claim the clear flaws of this agreement. charlie: -- the impact of law. richard: which hopefully the president would back. again, i think this is a seriously flawed agreement.

that is my own view. but, if it is going to come into effect, it is incumbent on the united states to address and compensate for those flaws. charlie: you've talked to a lot of members of the intelligence community in israel, or at least one. jonathan: the interesting thing is there is an impression in the united states that all of israel is against us. i think aipac and other lobbyists have tried to push that across. obviously, the political establishment in israel, including the labour party, is against the deal. but, if you talk to former intelligence officials, former heads of mossad, shin bet, which is the internal security service, people in the defense ministry, about 70 of them have signed a letter saying, look this deal might not be perfect. there are some real problems with it, but it is basically a done deal and it is harming israel to continue to object to it instead of moving forward to

focus on how will we convince president obama to really focus on interdiction of iranian arms shipments to hezbollah and a whole series of other issues they are worried about when sanctions are lifted. i think it is totally proper to focus on those downstream issues, but first you have to get to the point where the deal is approved. what was really striking to me about this speech today, which i think was one of the most important of barack obama's presidency -- this has been his top issue since the day he came to office because he prioritized nuclear weapons at the very top of his job. he raised the stakes in two important ways. he basically said the credibility, that was the word he used, of the united states was on the line. if the deal was defeated, we would no longer be the anchor of the international system of

collective security which has existed since the end of world war ii. we have been the leaders of the world in collective security and that would end if the deal were rejected. the other thing he did to raise the stakes was he intentionally delivered a highly partisan speech in which he was essentially saying to the democratic party, you desert me on this, you are no longer democrats. this is a bedrock issue for you if you are a democrat. charlie: if they desert him, he is in trouble. jonathan: right. the republicans need 13 senators to desert. it is not likely, but he is trying to make sure those 13 are not convinced by this powerful lobbying campaign. charlie: let's raise this question that was said about the speech and what the president said. if this deal does not pass, and we will clearly have a huge debate -- you can see it with lobbying and any other possible means to influence -- will it have that impact? will we no longer be, in your judgment, the anchor for -- you know.

mark: this deal is moving forward even if there are 80 senators who vote in a joint resolution of disapproval. it is moving forward because the statutory sanctions block that is in the legislation that supposedly will prevent the president from giving the sanctions relief under the deal could be vitiated by the president using executive orders, by de-designating iranian entities and declaring the central bank of iran -- one of the key legislative sanctions -- that it is unconstitutional. the president said that in 2012. the president is moving forward with this deal. nobody is killing this deal. the only question that one has to ask is how do we actually empower the next president to be tougher to actually implement some of the suggestions richard is making. to potentially go back and renegotiate key amendments to this deal, whether you think that is possible or not. the fact of the matter is in u.s. history, there have been over 200 international agreements where congress has said no, we want these amendments. presidents have gone back and renegotiated agreements.

some of those were major agreements in the cold war when the soviet union had thousands of nuclear missiles aimed at us. whether you think it could be done in legislation or through amending the deal, the fact of the matter is you need to empower the next president to negotiate tougher with iranians or implement the current flawed agreement in a much more vigorous way. i think a vote of disapproval would actually do that. jonathan: it pulls a thread on the whole deal. it would be disastrous for the united states. richard: i didn't much like the speech. i thought it was quite unpresidential. the fact he disparaged critics. he said were wrong about iraq and wrong about other issues. well, someone could say why should we listen to you, mr. president, if you were wrong about syria and libya? i thought it was way over the top. i thought he actually hurt his own case, but he did open the door on one interesting thing. he drew a parallel to the salt and start agreements. he said this is a temporary arms control agreement.

it will expire in 10 or 15 years on centrifuges or enrichment. there could be follow-on agreements. that is exactly the point. it is not so much amending the agreement. i actually think one of the things we should be doing is meet with the europeans, with the brits, the french, the germans, and potentially chinese and russians, and talk about the follow-on agreement. charlie: what about the gulf nations? richard: them too. we do not want after 10 or 15 years iran to become an industrial scale nuclear power. whether they technically have weapons or one screwdriver turn away from that, that is not an acceptable outcome. we ought to be thinking sooner rather than later about what is the follow-on agreement to this agreement. charlie: what is your sense on where senator schumer is? chemi: my sense is senator schumer is he is where he wants to be. he's in the center of the world and everybody is awaiting -- charlie: yes. chemi: that is before he makes his decision. charlie: i didn't ask for a commentary on the way senator schumer's ego is served. chemi: i don't have any special knowledge. if i had to guess based on what people -- charlie: you got people

reporting who know the jewish community. chemi: their assumption is he will vote against the deal. charlie: people talking to him the assumption is he will vote against it. chemi: he will not override a veto. charlie: he will vote against, but not override. chemi: that is true of many of the democrats, even those that are already coming out and saying they will oppose the deal. richard: after the initial vote to disapprove and then the presidential veto, that is when i believe the white house has to engage in a conversation with senators and congressmen about what are the u.s. policies being introduced into the mix. charlie: you are recommending they have a vote against? richard: i'm not recommending. charlie: what would be the best thing? richard: i think the best thing is the united states effectively has an addendum to this agreement which has three issues -- how do we deal with noncompliance? because the agreement is quite vague in many areas.

what are we going to do regionally to offset the fact iran will have more resources to pursue its -- charlie: hasn't the president spoken to that? richard: i don't think so. charlie: he clearly has spoken to that. whether he has spoken about it in detail -- richard: thirdly, how we will deal with the long-term nuclear challenge. charlie: he basically said we know some of the hundred billion dollars will be used for that but it is high on our own -- richard: but, what are we going to do about syria? because right now it will put iran in a better position to support bashar al-assad. what are we going to do in terms of other challenges that iran -- with hezbollah and hamas. it will be important to have this conversation. charlie: i will repeat what he says. he says we are trying to do that every day regardless of the agreement. richard: the agreement does exacerbate that to some extent. chemi: presumably, you would

jonathan: presumably, you would want that as a sense of a senate resolution, not as binding law. we have talked often about your view that the executive should have a free hand in foreign policy, so you wouldn't want congress tying his hands. just going on record with what he should do. richard: i can imagine a formal exchange between the two. the president could have a communication with senator corker. one way or the other, i think it is important countries in the region who are our friends understand -- charlie: if that is not possible -- richard: i think it will be possible. charlie: but if it is not possible, should this agreement be voted down? if it does not have the additional steps you are recommending, should this agreement be voted down, in your judgment? richard: it is a costly move to vote it down. but again, i think in order to get the votes in order to pass this you need to do this sort of thing i am suggesting. charlie: why is it costly to vote it down? the sanctions will already fall apart? richard: a bit of that. the chinese and russians will clearly go. the europeans to some extent will. the global perceptions of the united states -- i don't want to compare it to the league of nations. that is overly dramatic, but there is a sense we have gone far down the pike and for the united states to not act in a unified way, despite our constitution, would be

problematic. then it is what iran would do. i think the president may have overstated it that it is war or diplomacy, but there is the question of whether iran would use an american vote to disapprove as an excuse to once again -- restarting some of his its activities and that is a possibility. jonathan: we would get the worst of both worlds if the deal is rejected. we would have no eyes on iran and their program. and we would basically incentivize them to race toward developing a weapon. no sanctions. the idea that somehow sanctions are going to be reapplied, that china and russia which have a veto in the security council who the president has convinced -- charlie: do you believe it would make inevitable the use of military force, too? jonathan: inevitable is a strong word, but i think the president is right. that it dramatically increases

the likelihood of military action that is unpredictable. people who want to start wars are not quite sure how it will end. mark: i disagree with that. the president said over and over again that no deal is better than a bad deal. charlie: everybody says that. mark: when he said that, he must've instructed the entire interagency to come to him with a comprehensive plan of alternatives which included the possibility of military force, but also the use of sanctions, of diplomacy, of cyber sabotage, of covert action. he must've had a very comprehensive alternative plan. i'm sure we would all be very interested to know what was his alternative to the deal because no responsible commander in chief would go into a negotiation, particularly with a hardened negotiator like zarif or rouhani, without an alternative. he had an alternative. let's look at what the alternative is. i've testified five times before the u.s. congress in the past two weeks and i have done detailed scenario planning on what are the alternatives. and i disagree with that. after spending a decade working

on sanctions, people fundamentally misunderstand we don't sanction countries. the genius of what the u.s. treasury department did and what the u.s. congress did is they essentially created an environment of risk so financial institutions, energy companies and insurance companies made a fundamental decision -- you either have access to the $17 trillion u.s. economy or the $400 billion iranian economy. if you make the wrong choice there will be consequences. many companies paid that price. i don't believe on a congressional vote of approval that these companies will be rushing in. i don't buy this argument that there will be some gold rush. i think they will be very cautious about going back into iran because of the counterparty risk, and more importantly, the political risk. charlie: i read one story after another of how people are lining up to go back in if the sanctions are lifted. chemi: the alternatives that were prepared by the administration in case of failure were in case there was no deal -- the p5 plus one -- we're all in agreement there was not any deal. the iranians were cast as the

villains and the administration had an incentive and an interest and stood behind and maybe made the sanctions tougher. that is not what's going to happen if the deal gets voted down. iran will be the victor. it will have achieved one of its greatest diplomatic victories in international arena. the europeans will be sort of flummoxed on what to do. russia and china will be rushing in and the united states will not be enforcing sanctions against, say the bank of china. so, the alternatives existed but they no longer exist under those circumstances. mark: now you are admitting there were alternatives. now we have to discuss the delta between what were the alternatives and what are the alternatives now. i don't accept the argument all those alternatives have vanished. i think we need to do a systematic analysis of what the alternatives are. i would recommend the u.s. congress ask the administration for an analysis of what were the alternatives, what are they today and what is the delta between those plans.

jonathan: you can't have 535 members of congress negotiating for the united states. that is not the way we work. mark: chairman bob corker and the senate foreign relations committee. jonathan: i'm not saying they can have a role, but you can't have them negotiating. as far as the unilateral american sanctions, we tried that in the bush administration. it did not work. they went from almost no centrifuges to thousands of centrifuges with that approach. the idea that our economy is so strong that our sanctions alone is going to bring them back to the table is a fantasy, and a dangerous fantasy, because it is at odds with logic and the realities of international relations. mark: the iranian nuclear program did not surge forward. they did not accelerate the program massively. they move incrementally. if you know anything about the iranian nuclear program, you know the iranians move their program forward incrementally. they did so in the bush administration and they have done so in the obama administration. jonathan: from a dozen centrifuges to 19,000

centrifuges, that is not so incremental. mark: 1800 a year. ♪

charlie: with respect to the previous existing agreements on weapons, how could he have made

a better deal? where is he wrong in terms of what he could have done? richard: getting the iranians down to zero was impossible. i think that is a red herring. was it necessary to throw in lifting the ban on conventional arms sales after five years, ballistic missiles after eight years? charlie: my point is he so believed in the deal, he was prepared to make that concession. richard: we had different positions for example on the duration of the limits on centrifuges and enrichment. we went in with much longer durations, the iranians want shorter ones. we split the difference. are you telling me that we couldn't have insisted on getting something better? just for example, what if we had congressional members of the delegation the way we did during the salt and start agreements? what if he used congress as the bad cop? john kerry would have said to zarif, i cannot do certain things because congress will not approve the deal. the relationship between the executive and congress got so

poisoned during this process that the administration did not even use congress in ways that could have helped them. charlie: what was it that could have been achieved that was not? richard: i believe we could have got longer durations. i don't think we would have to have throw in some of those sweeteners. i think some of the compliance provisions are ripe for mischief down the road. now, it would have meant having the europeans on board some of those tougher positions. i think it might have been possible. the french were leaning in that direction. with the iranians, they are tough negotiators. this is a little bit of a game of chicken. we would have had to be prepared at times to walk. one of the things the administration would have had to think harder about was taking as much as they did, military force, off the table. the incantations that no options were taken off the table, nobody believed that. charlie: is the reason the president was not prepared to walk was because he was too anxious for a deal? is that your judgment? richard: i think he was too anxious to avoid -- to have to potentially use military force. charlie: so he was prepared to make a bad deal in order not to use military force. i'm just trying to go to the logical extensions of your point of view.

richard: he agreed to what i believe is a flawed deal and there is not a deal that i believe was as good as he could have got -- charlie: in order to avoid military action. richard: yes. he thought that this was necessary to avoid having to commit to use military force. with all the uncertainties, that could have brought into play. i say that is why now we have to find ways of compensating for that down the road. charlie: you agree with that? jonathan: it is a moot point and kind of a minor point. let's stipulate that on conventional weapons we could have done better. ok. conventional weapons are nothing compared to nuclear capability. in the larger scheme of history. when you talk about historians obama kept his eye on the right priorities which are nuclear, to keep the club closed. and it dwarfs every other factor and somehow it is getting

conflated. these very legitimate issues on hezbollah and proxy wars are very important issues, but they are not nearly as important as the nuclear issue and they are getting conflated as if they are important. richard: this does not keep the club closed. this compromises important dimensions the entire nonproliferation regime. this is an expensive agreement. you may think it is better than the alternatives. you may have thought it is worth it, you may have disagreed with it, but this is an expensive agreement. jonathan: it keeps the club closed in the short run, there is no question about that. charlie: the president went out of his way to express thanks to russia in terms of whatever support they gave him. richard: russia will be critical if there is a chance on moving on syria. russia is a less difficult candidate to partner with than iran, but if you can bring russia into the tent, it gives you more leverage with iran. that would be tremendous if it were to happen. jonathan: putin told jimmy

carter not too long ago that he wanted international conference and carter conveyed that to president obama so there is some discussion now about whether they can get all the parties together and have a conference on syria. charlie: they want to talk about it to as many people as possible. mark: the problem with the gulf nations is that the saudis have already made it clear through former ambassadors that they want the iran deal. they used to be the gold standard where countries were actually agreeing to get civilian nuclear technology if they didn't enrich or reprocess. now we have the iran deal where the leading state sponsor of terrorism can enrich and reprocess. the saudis have made it very clear they want that deal. the notion that we will have the saudis who have the money and can buy the expertise and have the strategic interest, getting the same kind of nuclear threshold capability that iran has and that will expand over time, i think it is the death now for nonproliferation in the middle east and maybe elsewhere. that is the serious consequences of this deal. maybe we could stop them. the u.s. administration's response to congress when they

ask them this question is not to worry. no other country would want to go through the severe economic pain iran went through in order to get that capability. that is a great answer except when it comes to the saudis, we will not cut off saudi oil exports. designate the saudi central bank and kick multiple saudi banks off the banking system. we will not have the same kind of sanctions tools to use against the saudis, or the uae or even the south koreans, for example, who want to have the same kind of capability. that is the problem that this deal will trigger. not a proliferation cascade -- charlie: if iran gets a nuclear weapon. mark: no, not if. short of that. charlie: reaching the threshold. mark: they are at the threshold now. richard: the president said in the npr interview, the breakout time will grow, but from years 10, 13, 15, the breakout time will shrink. iran will get to the threshold under this agreement with all the uncertainty of what comes afterwards.

charlie: unless something changes. richard: unless there is a follow-on agreement. jonathan: saudi arabia has zero program and if they race towards importing all kinds of foreigners to develop programs it would create a huge crisis in u.s.-saudi relations. mark: they just signed a multibillion deal with the russians and with the south koreans to build a "civilian nuclear program." charlie: we have more to discuss than we have time. thank you for coming. back in a moment. stay with us. ♪

charlie: we continue this evening with a look back at 16 years of "the daily show with jon stewart." the host of the nightly comedy central show announced in february he would leave the program. the finale is airing tomorrow night. here's a look at what jon stewart and other guests on this program have said about "the daily show" over the years. what do you enjoy the most about? jon: when it feels relevant. when you feel like the anger or the humor you would feel in something that most of the people in the country have some idea of or some opinion of and you can get it out there that night, then it feels really relevant and that is the most enjoyable thing in the world. george: during the lead up to the war, and certainly in the beginnings of the war, you could argue some of the best news was coming out of that comedy show. they were actually bringing up

issues that weren't being talked about in other places. charlie: are they only getting their news from jon? george: that's not jon's fault. that's saying there's a lack somewhere else of real information. stephen: i know something about his politics in terms of i know something about comedians' politics. they tend to be iconoclasts and they tend to be anti-status quo and a lot of comedies about tearing down status or status shifts. jon is admirably balanced, however people may characterize him. every time i ever worked with him on something, he tried to perceive what was the true intention of person speaking left or right, whether or not it was something he agreed with because he wanted to be able to honestly mock.

>> i think he is one of the most important voices in information in this country just because he delivers it with a comedic point of view, does not diminish its importance. john: the audience looks at jon to help them articulate painful feelings. something like a trayvon martin verdict, people are looking to jon. jon;: once you establish a rhythm to work the show, you are trying to we bought it and -- ev olve it. your voice will become somewhat predictable and 20 years from now we will meet on a panel and the real old and new comedy satire guys will interview us for a little segment on hbo which by that will be on tv. that will be that. that is not the measure of your

life. that is not the measure -- the measure of it is to be proud of what you are doing and work with people you enjoy working with for his long as you can do it. charlie: joining us from washington is dan pfeiffer a former senior adviser to president obama on strategy and communications. in new york, a contributor to the new yorker magazine. also at the table, brooke gladstone, a host and managing editor of "on the media." and dave itzkoff, a cutl lture reporter. and we have a media observer for the new york times. i'm pleased to have them all on this program. what is the significance of what jon stewart brought to us? >> he helped get rid of crossfire on cnn. [laughter] he shames jim cramer.

he got obama on his show seven times. ken: he made us laugh but not just that the jokes but at ourselves as well. i think he is a significant -- charlie: is it what he did about fox some of the most pleasing aspects for you? ken: oh, yeah. i thought the fox thing was just great. talk about holding him up. when they attacked him as they did recently. he did not get defensive. brooke: i think what is particularly interesting is there was a poll in may that have a question does jon stewart reflect your view of the world? 52% of the respondents said yes he does. of republicans, it was 40% of

republicans. charlie: is it the rhetoric he has rather than the ideology? brooke: that is where the significance comes in. we all know about the 2009 poll where he was voted most trusted news man in america, displacing a famous 1970's all with walter cronkite. it is because the digital world has changed the role of the person presenting information. it is no longer the voice of god in the clouds. the playing field is leveled. transparency is the new authenticity. that is what you trust, not authority, not objectivity, which everyone knows is a bit of a myth. charlie: transparency and authenticity? brooke: transparency is the new authenticity. it replaced it as a generator of trust.

>> he was honest. what he was doing was honest. he came out and said what he thought but he also backed it up. nobody did more research than that show. other media outlets were embarrassed because he found things nobody else could find. bill: his staff would find a clip. somebody would say something and then he would say yeah this is what you said five years ago. the exact opposite. he would be able to honestly portray a person and hold them to account. his point of view was very important. a lot of times in late-night, they try to obscure their point of view. he did not do that. he showed his passion but it was really honest. >> i think part of the pleasure was watching the viewpoint evolve over the 16 years. i remember the show debuting. he inherited it from craig kilborne. it was maybe a watered down

saturday night live weekend update kind of show. through world events shaping perspective, you had the 2000 recount, the events of 9/11 the crossfire appearance in 2004. you had the last five years of just political turnover and racial issues. dave: i think jon stewart is somebody who came by his perspective honestly. charlie: before we go to dan pfeiffer, this is a clip having to do with crossfire. jon: it is funny. i made a special effort to come on the show because i have privately among most of my friends and occasionally television shows mentioned this show as being bad. [laughter] and i felt that was not fair and i should come here and tell you it is not so much bad as it is hurting america. [laughter]

i wanted to come here today and said -- here's what a want to tell you guys -- stop. [laughter] stop stop, stop hurting america. and come work for us because we has the people -- >> how do you pay? jon: no wellt well, but you can sleep at night. we need your help. right now, you are helping the politicians and corporations and we are left out there. you are not too rough on them. you are part of their strategies. you are partisan, what you call it hacks. charlie: was that the end of crossfire? >> the head of cnn came out and agreed with jon stewart and agreed. charlie: dan pfeiffer the president appeared five or eight

times? dan: seven times. charlie: why was a good for the president of the united states to go on jon stewart? dan: jon stewart embodies two two things that happened -- the digitalization of the news. jon stewart influence was not just what people saw as they were watching comedy central at night. it was in the clips shared on facebook and twitter on the various things he would do and he came of age at the exact time our politics and media were getting absurd. he pointed that out and away nobody else would which is why so many people particularly young people who were part of the obama coalition, watched. if you are going to communicate with young people in america, you have to talk to jon stewart. he became someone not so influential that the president would just go on his show summary the president will call into the oval office and talk to just as you would do with anchors of the network news.

that was a voice that really mattered. probably more so in some ways than your traditional newsreader anchor because he would carry that point of view whether it was getting the 9/11 workers bill passed or -- he was beating the president of nonstop about healthcare.gov. we were very concerned jon stewart would turn people off. charlie: beyond the fact he wanted to reach his audience did anyone learn something from jon stewart? dan: the president had tremendous respect for jon stewart as an entertainer a personality, somebody who is smart. the president would say the interviews were some of the toughest he would do -- in a different way with an interview with you or others because you never knew where he would go. in 2012, we did an interview with all the network news anchors and the only person in the entire campaign who asked the president about drones was

jon stewart. he would think about things that were not just the immediate political fiasco of the day. that made it hard to prepare for. charlie: let me go to that jon stewart interview. ken: one of the things that enthralled me about him and the audience is that there was a sense of danger on his show. you did not know what he was going to do. brooke: jim cramer knew. ken: you are sitting there kind of tense and curious. brooke: i was reminded about his first interview with rick santorum which was a great disappointment. it seemed so conventional. there were no difficult questions asked. i turned to my husband afterwards and said he just rolled over on that one. the next day, jon stewart came back and said we have gotten a

lot of feedback with my interview with rick santorum. some people said it sucked and some people said it sucked. who does that? charlie: that is the transparency you were talking about. >> he talked about rumsfeld and said he missed it. he would make fun of the fact that people should not trust him as a newsman. he took it seriously. he knew the audience was paying attention to what he said and he was responsible. dave: even the way he handled his exit. these retrospective clip packages are always self-deprecating. it is always making fun of how bad his singing voice was or how badly did in celebrity interviews. ken: he would deny up and down that he was a journalist. i would say what you are doing is journalistsm and he would

say no. bill: i would say you were not really any different from thomas mast or mark twain or will rogers. you are a satirist, but you have journalism in your bones and he said no, i'm a comedian. you would emphasize that all the time. charlie: did it hjaave an impact when he was critical of the president? he pointed it out to the audience. dan: we feared his criticism because it had more influence than a somewhat more traditional journalist. particularly, his first interview that dave recounts in the new york times the other day was one where we went into it with high hopes it was right before the midterm elections and hopefully people were watching it. he skewered the president. the stories that came out of that was obama lost the liberal

base because jon stewart was tough on him. he was an influential voice. when he is for you it is great. bill: he basically said this was a disaster. he said he would download every movie of all time. basically because he did, the republicans were hating them for it. but when he did it, they said it was a disaster. charlie: what did the president talked to jon about? dan: i was not in the room for it. the president kicked all the staff out for it which is assigned for respect for jon stewart. the genesis of it -- it was around the time healthcare.gov was happening. our biggest concern was that jon stewart would continue to hammer us after it was fixed and we were worried that young people would not sign up for health

care because they thought it was the broken. you mentioned the sibelius interview which goes to the danger of stewart. you could go in and it could have a fine interview. or he can take you down. i worked for tom daschle many years ago, long before same-sex marriage was an issue the country moved on. tom daschle went in there during the debate around the constitutional amendment on marriage. jon stewart pushed him really hard on white it would be wrong -- why it would be wrong for same-sex marriage and called him out before any journalist anyone else was doing that. you never knew when that would happen. charlie: why is he leaving? dave: i don't think anybody knows exactly. he got to scratch an ithc when he made "rosewater." he expressed the idea he wants

to spend more time with his family. it is unthinkable he will ride off into the sunset. bill: in any endeavor when they say that, they usually have been fired. [laughter] in jon's case i absolutely believe that. i interviewed him when he was doing the oscars -- charlie: not a big success. bill: i was interviewing him on the west coast and he said it is bedtime, excuse me. he got on the phone and told stories to his children on the phone. he is very involved with his family. when he announced it, that is credible to me. he is never home for dinner with the kids. he will find another outlet. charlie: what will he do next? because there are some people who believe you find one show that is so you. david letterman, the show he does. ted koppel and his show. you become so part of it, it is

your show. bill: sometimes you get tired of doing it. i could imagine he felt spent. brooke: he himself said you don't need a flaggin g host. you need one that is 100%. he was tired. i interviewed him right as he was taking his job. he said people ask me, you know, do i feel i ever accomplished anything? up until now, before he took the daily show job, what did i feel really good about? first, i felt nothing and then i thought yes, i left jersey, came to new york became a comedian and got to express myself. he said that before the daily show and maybe he has done what he can do. maybe he has run out of strength. bill: he is tired but he does say i know i will never have a job like that.

this is the thing for him. he is not going to have this outlet again. he knows that, but i think he is spent. dan: you can believe he is comfortable in his own skin and that goes through the tv. charlie: what is interesting about all the late-night arena is how much of it is about politics. politics is the daily fodder of late-night television. you would think there would be more people like, not just doing what jon did so brilliantly, but more political satire. dan? dan: i think the internet will breed not 1000 jon stewarts but a lot of people doing what jon stewart did. to give you an idea of how influential it is, in the white house you get clips every day that run through the news what was on the tv news. about three or four years ago

, we started pulling all the late-night monologues and driving public opinion. if something happens and it is getting hammered every night by stewart ofr fallon, people start to know about it pretty quickly. we started to monitor that to see where public opinion was going. it is something the white house looks at everyday. how influential that has become as media disaggregated and people trusting the media less. brooke: don'tdave: they have gotten less political. they are late-night shows. the monologues have become the least important component of the show. bill: i do think what the monologues do -- this is interesting -- they create the

narratives. there is a narrative for what happens. all the comedians are going after that narrative, it reinforces it and the country starts to sink it in. the interesting thing about obama is he has never been identified in a way as what is his comic thing? clinton was a hound. and bush was-- -- yes, a hound. charlie: jon stewart would have a better word. bill: bush was kind of a dope but obama is aloof. he has been harder for them to define and that is one of the reasons that has not been quite as much. charlie: do you agree dan? dan: i do. we have been fortunate not to have that idea hammered into the public every day, but this will give you another sense of how important it is -- this is all forgotten, but in 2007 when the

president was running against hillary clinton, we were looking for ways to draw a contrast with her. one of the ways we found was the president had a guest appearance on saturday night live where he got to take a pop at her. that went viral and that was worth way more than the time it took to go to new york and do it. i think the presidential election will determine whether how much politics and comedy will stay intertwined because it was a huge part in the last presidential elections. if donald trump is the nominee i guarantee there will be this as well. charlie: david letterman said the one reason he regretted leaving was because of donald trump. what do you think donald jon stewart will do? ken: i know i will see him at mets game. i have no idea. bill: i don't think johnn knows. he showed up at a comedy club a

few weeks ago to do stand up. i think he will probably do more of that and then figure out maybe another movie or something. he will do something substantial . the guy is so bright. brooke: i thought when hedave: i thought when he made "rosewater" that was a great curveball. charlie: he wants to make another film? dave: it took some doing to get the arrangement with comedy central to get the time off to make that. now that he has a completely clear schedule an infinite canvas i wonder if he will look for those stories that he can bring attention to. charlie: late-night continues to fascinate. thank you, dan. nice to have you. good to see you again. thank you for joining us. see you next time. ♪

♪ shery: stocks falling for the fourth time in five session, dry down by media. a first quarter profit surge at sprint triggers shares -- plans for a buyback. and a long, winding road to the white house. happy friday. i am shery ahn.