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U.S. Kills Key ISIS Figure in Raid in Syria; FBI Forensics Team Joins Amtrak Investigation; Boston Marathon Bomber's Case on Appeals; Jeb Bush Struggles to Clarify Iraq Position. Aired 1-2p ET

Aired May 16, 2015 - 13:00   ET

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

[13:00:02] ANNOUNCER: This is CNN breaking news.

FREDRICKA WHITFIELD, CNN ANCHOR: Hello again, everyone. I'm Fredricka Whitfield, thanks so much for joining me.

We begin with our breaking news. A major development in the U.S. war on ISIS. In a risky operation, U.S. Delta Force commandos kill a key ISIS figure in Syria, Abu Sayyaf. A man who controlled ISIL's illicit oil and gas operations. A senior U.S. official tells CNN that we'll learn that the extent of his -- of this CFO after we exploit the materials we took off the objective. He was not significant. This mission is really going to unsettle ISIS, however. And this is just the beginning in Syria. Watch and listen closely. Much of it won't be conspicuous but it will be telling and accumulating.

That statement coming from a U.S. official.

Barbara Starr first broke the story this morning. She joins us now from the Pentagon and national security -- and national correspondent, I should say, at the White House, Sunlen Serfaty.

All right. Barbara, you first, every hour we are learning more details. Tell us about this raid that killed this key ISIS figure.

BARBARA STARR, CNN PENTAGON CORRESPONDENT: Well, who was Abu Sayyaf? That is the key question at this hour. Not a lot of people have heard of him but I can tell you, U.S. Special Operations, the U.S. intelligence community, knew about him and clearly knew he would be at this location when they took off on this raid.

What we are being told by officials directly familiar with the operation on the ground overnight in Syria is don't think of him as just the oil and gas guy for ISIS. Important, though, that may be that Abu Sayyaf, they now believe, had taken on an increasing role in operations, in planning, in military affairs of ISIS, and possibly they are looking at indications he had been in contact of some sort with Abu Bakr al-Baghdadi, the leader of ISIS.

All of this added together is what made it worth the risk, they say, to take the plan to President Obama, get it approved, and send those Army Delta Force commandos deep into eastern Syria overnight. The idea had been, the mission had been, to try and capture him and his wife to bring them back, their computers, their laptops, their cell phones. This was an intelligence-gathering mission to get everything they

could about what these two people knew. Now the wife is back in Iraq, undergoing interrogation. But Abu Sayyaf was killed when he resisted, we are told, in a firefight with those Delta Force commandos.

How tough was that firefight? We are now told that hand-to-hand combat broke out between both sides -- Fred.

WHITFIELD: And so, Barbara, given the high risk, what was it about this operation that national security and the White House felt this is the only option, this is the best way in which to take out this target and collect more data?

STARR: Well, think about it this way. You know, we've seen an awful lot of airstrikes by the hundreds, drone operations against suspected terrorism figures. But this time they didn't want to do it that way because it wasn't about killing him. It was about trying to go in, capture him, and all of the information that might be at the place, the location, where he was staying.

This is something, you know, behind the scenes that Special Operations Forces have done for years. We saw a similar operation obviously in the mission that killed Osama bin Laden in his compound when the Navy SEALs scooped up all the data, the drives, the computers that they could. We've seen it over the years, time and again, inside Iraq, inside Afghanistan.

When you go after a high value target, if you want to capture or potentially kill that target on the ground you also want to scoop up every piece of intelligence you can find -- Fred.

WHITFIELD: All right. Barbara, thanks so much.

Let me bring in Sunlen Serfaty on this as well. So we're getting response to this raid. House Speaker John Boehner released a statement just moments ago. What more can you tell us about what is being said?

SUNLEN SERFATY, CNN NATIONAL CORRESPONDENT: That's right, Fred. Speaker of the House John Boehner just releasing a statement, of course, expressing his gratitude to the U.S. Special Forces who carried out this mission but added this, quote, "While I'm encouraged by today's good news I remain gravely concerned by ISIL's assault on Ramadi that threatens the stability and sovereignty of Iraq which is vital to America's interests."

Now we know that Iraqi forces right now are desperately trying to keep control of that key city, this after ISIS has made some advances in recent days. Yesterday afternoon raising their trademark black flag in some -- on top of some government buildings. Now on Friday the White House announced that they are expediting weapon shipments to Iraq. This was communicated by vice -- from Vice President Joe Biden to the Iraqi prime minister on a telephone call -- Fred.

WHITFIELD: And, so, Sunlen, is there any interpretation from the White House as to how they measured this risk? Did they feel that this was a large risk to take or just one that was necessary?

[13:05:11] SERFATY: Well, it certainly was a risk, as we know from Barbara Starr's great reporting all morning. But we are seeing some pushback from senior administration officials, really more of an explanation, why this risk was taken on. And again, ordered directly from President Obama himself after an assessment from his National Security team. They call him a senior ISIS leader. And someone that might have had some sort of communication with al-Baghdadi. Of course, this main ISIS leader that they wanted to -- that they've been chasing for quite some time.

So there was the indication that he could have been in communication with him in this role that he had been and we know from a senior administration official that the directive was to capture him, not to kill him. Of course, once he started firing on U.S. forces, that is when those forces made the decision, as they have the capability to go in ahead and kill him.

WHITFIELD: And then quickly, Sunlen, do we know whether or not the president watched this? We know that he was able to watch the taking out of bin Laden. Everyone remembers the still picture of Hillary Clinton's expression as well. What about in this case? Do we know?

SERFATY: Well, we asked that specific question of the White House, Fred, did he watch this from the situation room, was he watching or learning information in any sort of real-time capacity. Now the White House tells us that the president was regularly briefed on the operation by his National Security staff but would not say anything beyond that. And we don't expect at this time for President Obama to be making a statement -- Fred.

WHITFIELD: All right. Sunlen Serfaty, Barbara Starr, thanks to both of you. Appreciate it, ladies.

All right. As we just heard, the secretary of Defense says this will be a significant blow to ISIS.

Let's bring in Lt. Col. James Reese. He is a CNN global affairs analyst, a former U.S. Delta Force commander.

Good to see you. You were part of the Delta Force conducting raids. So what's your best guess as to how this one unfolded?

LT. COL. JAMES REESE, CNN GLOBAL AFFAIRS ANALYST: Fred, good afternoon. Well, bottom line I will tell you, with the entire JSOC family out there, what they have is these are battle drills. They've been doing this thing for years since 9/11. Now when we were in Iraq, they were turning this type of operations seven, eight, 10 times a night.

Now once we have left Iraq, now we don't have that what I'll call home-field advantage we used to have, it's a lot more riskier and there's more planning that has to go into it. But these forces from JSOC, they how to do this, and they do it all over the world and they're the best at it. What I will tell is one of the reasons I believe the president had to

get involved here was because it was a cross-border operation into Syria, putting boots on the ground, and not for hostage rescue, and the reason JSOC goes in is because this is part of this network, you have to defeat -- you take a network to defeat a network.

When they go on to get Abu Sayyaf that one -- that becomes one piece of the puzzle to try to get together, it does become an intelligence operation, and use that intelligence to go after the rest of the network.

WHITFIELD: And you heard from our Barbara Starr, she's been reporting all afternoon long that reams of data have been collected from this raid, some of that data, perhaps, is in Iraq and being extrapolated or maybe some of it is making its way state side.

How do you see this kind of information being pulled from the cell phones and these computers? Would that be while in transit? How immediate will those results be?

REESE: It's both, Fred. We have the capability now to do on the spot exploitation of cell phones, computers. There'll be people who literally can look on the target to see if there's anything to drive that assault force to another target right away if need be. So that happens on the target very quickly.

Then now over the years, the exploitation capability, the joint exploitation forces that are brought it to do all this exploitation, to bring all the intelligence out is quickly brought in where years ago, it used to go to a warehouse and sit. Now it becomes actionable, there's folks across the intelligence community that are going in, dwelling through it, gleaning the information and getting it back out to the forces and to the command to make sure we can drive the next piece to bring this threat work down.

WHITFIELD: This can't be a coincidence, can it, that this operation will be taking place just days after we hear that ISIS taken control of Ramadi there in Iraq? Do you see a connection here?

REESE: Well, I don't, Fred. I mean, JSOC, their role and their mission is the senior leadership of ISIS. Just like it's the senior leadership of al Qaeda. It was the senior leadership of the Baath Party when we first went to Iraq. They are laser focused on these people because they know if we can knock out -- and literally we want to capture these guys, we get that information. Unfortunately they turned we've got to shoot them, it kind of brings it down a notch.

But it's not, you know, just a coincidence. And there could be another raid tonight somewhere else for someone else if something gleans out of this.

[13:10:06] WHITFIELD: And then Abu Sayyaf's wife, Abu Sayyaf being the one who was killed, his wife apparently captured, taken to Iraq and being interrogated. To what degree? What kind of information do you think they really could anticipate from her? REESE: Yes, Fred, this is us getting better through the years. Back

in 2002, 2003 we would never think of doing this. But now we realize that, you know, their whole -- their whole web is intertwined. We started doing this in Iraq, looking the different members of the family to capture them, to go after and get that key -- that key leader then and call him in.

I guarantee you, she knows what's going on, as CNN has been reporting, we believe that she has some elements of, you know, exploitating women within ISIS. She'll be a good capture there. And the intelligence people will be working her hard.

WHITFIELD: All right. Lieutenant Colonel James Reese, thanks so much. Appreciate your insight.

REESE: Thanks, Fred.

WHITFIELD: All right. Sunday, CNN goes inside ISIS. Watch "BLINDSIDED" a Fareed Zakaria report. It's right here on CNN tomorrow night at 7:00 Eastern.

(COMMERCIAL BREAK)

WHITFIELD: All right. Welcome back. I'm Fredricka Whitfield.

A new development today in the Amtrak crash investigation. The National Transportation Safety Board says it is looking the possibility that some damage to the windshield of the train may have been caused by some sort of projectile, hitting it before it derailed. Train 188 could be just one of three trains hit by objects that night.

Erin McLaughlin is live for us now in Philadelphia following the investigation.

So what more do we know about the damage to these windshields and what role the FBI is now playing.

ERIN MCLAUGHLIN, CNN CORRESPONDENT: Hi, Fredricka. That's right. Investigators have said they're very interested in a circular marking located on the lower left-hand side of the windshield. They say it's fist size. They say that they believe it was there prior to the crash, possibly caused by some sort of projectile that struck the train. And they're calling in the FBI's forensic team to analyze that further.

[13:15:16] In addition to that, there's more evidence, new evidence, from the assistant train -- assistant train employee who was on -- the assistant conductor, rather, I'm sorry, that was on the fourth car of that train. She says that just before the train crash she heard radio transmission take place between the Amtrak dispatcher and an engineer on a separate SEPTA train that was in the nearby area.

That engineer told the Amtrak dispatcher that the SEPTA train's windshield had been struck by some sort of projectile. After that, she said she heard from the Amtrak 188 engineer say that his train had also been struck. Deepening this mystery, we are hearing from passengers that were on

board a separate Amtrak Acela train that was in the vicinity that night. This passenger tells us that about 15 to 20 minutes before Amtrak 188 derailed an unidentified projectile struck one of the passenger windows on that Acela train. Now initially, authorities had discounted these reports as being unrelated to the Amtrak 188 crash, but clearly now taking another look -- Fredricka.

WHITFIELD: All right. Erin McLaughlin, thank you so much. Keep us posted on any new development.

So let's take a closer look at what's next for this investigation. Joining me right now, Dr. Mitch Garber, a former NTSB senior medical officer and senior managing consultant with CSI.

All right. So you've investigated these types of accidents before. What are they looking at now? How are they zoning in on these potential markings on the windshield specifically on this Amtrak's lower left hand side they had mentioned?

MITCH GARBER, FORMER NTSB MEDICAL OFFICER: And so obviously, they're -- they're going to be very, very concerned, Fred, with when did this happen and how did this happen. What was it that actually did this? You can imagine at the speed that this train is going an impact of that sort, even something relatively small, is going to have a tremendous effect on both the windshield and the noise is going to be incredible.

This is going to be a potential distraction to the engineer. I think that's the big concern that the NTSB has got right now is, is this possibly -- could this have something to do with why the engineer was not attentive to the speed as he should have been under the circumstance.

WHITFIELD: At the same time you mentioned noise. When you're on a train it is noisy. When you throw in the Amtrak or the Acela, it's very noisy. And particularly is the case if you're the engineer here. So given all of that extraneous noise to hear an impact or to see something hit the glass, it would seem as though that might not be a huge distraction for an engineer.

GARBER: Right. And the one thing that's really important here is this is not -- this is not a necessarily unique even to the scenario. Stuff hits trains, they're going fast, they're going through corridors where there may be debris.

WHITFIELD: Right.

GARBER: Even during the accident sequence there may be debris so it's very important to ensure that this did in fact happen before the accident and not as a result of it. But when that's happening, yes, there are a lot of things going on and in this particular case, the engineer should have been attending to those speeds, in spite of what distractions may have been there. And so again the NTSB is going to be looking at that as well. Was this engineer's training, was his background, was his ability to attend to the things that he should have been attending to as it should have been?

WHITFIELD: OK. And so we heard through Erin's report there was another Amtrak employee who was in a different car on this Amtrak, who remembers hearing the radio transmission that perhaps there was something may have struck a SEPTA and maybe even Acela which is a higher speed, you know, train along that northeast corridor. And now they're going to be comparing the kinds of impacts, you know, how will they try to determine whether these are similar? You know is the glass similar? I mean, because there are lots of different factors here, even if you have the same kind of projectile, the impact might look different.

GARBER: Absolutely. I mean, there's no guarantee there's even the same type of projectile. If somebody is hurling rocks, as an example, at these vehicles, then it may not be the same type of rock each time it hits them. So I think they're going to be looking at the mechanism of the damage, the types of speeds it would be required to create this. The types of locations that this could have come from. And a lot of that information is going to be wrapped up into ballistics testing. Even testing of this particular vehicles with these particular wind screens to see what types of events could have caused them and the FBI and those ballistics forensics folks will be very involved in that part of the investigation.

WHITFIELD: And then of course the most obvious question a lot of people have is, OK, so something hit the windshield, how does that explain the fast acceleration of this engine?

GARBER: Right. And that's what's really important here is there was apparently, and again they're looking at the data recorder, the event recorder right now, to see what kinds of information they can from that. But one of the questions is not just this idea of did this -- could this have been a distraction? But why was the -- what was the engineer doing in there and were they doing it appropriately regardless of the distraction?

[13:20:11] It looks like there may have been a speed increase during the time when we'll be expecting a speed decrease. If that's the case, this doesn't necessarily explain that and there's going to be additional investigation. It may end up --

WHITFIELD: That curve is always there and he has done this route before so there is that familiarity.

GARBER: There is, and it may end up that this actually something of a wild goose chase. That this may not have anything to do with the accident. And that's going to be something they'll be looking at as well.

WHITFIELD: All right. Thanks so much. Very complicated investigation made even more so now.

Thanks so much, Mitch Garber.

All right. The Boston marathon bomber sits on death row today but legal case is not over. We'll take a look at his automatic appeal and see how long it just might take. Next.

(COMMERCIAL BREAK)

WHITFIELD: All right. Legal experts say it could be years before Boston marathon bomber Dzhokhar Tsarnaev is actually put to death. A federal jury sentenced Tsarnaev yesterday afternoon for his role in the bombings but that death sentence now sets off a series of lengthy appeals.

Joining me right now from Boston, CNN commentator and legal analyst, Mel Robbins.

Good to see you, Mel.

MEL ROBBINS, CNN COMMENTATOR AND LEGAL ANALYST: Great to see you.

WHITFIELD: So these appeals, this is automatic?

ROBBINS: Yes, it is automatic. And the reason why it's automatic is because of the high stakes in a death penalty case.

[13:25:04] And let me explain briefly what's going to happen, Fredricka, is that these appeals will become automatic, they'll get filed immediately, and basically what's up for grabs in terms of the appeal is many of you will remember there was a huge fight over the venue, and whether or not it should even be in Boston. And you can bet your money on the fact that one of the big appeals will be that Judge O'Toole was made huge reversible error and that biased the defendant by not moving this case out of Boston, they way they did, for example, with Timothy McVeigh.

WHITFIELD: This is so perplexing, though, right, Mel, because we're talking about somebody who wanted death. He expressed that already. So now he gets the death penalty by way of a jury and so it would seem that his sentiment would weigh on the appellate panel's mind as to whether to even exercise an appeal process?

ROBBINS: Well, you know, it's interesting that you say that and, you know, in the case of Timothy McVeigh, he actually let go of the appeal process midway and that's why they were able to execute him within four years because he disband the appeals. But I've heard a couple of experts on our channel say something fascinating, which is these weren't suicide bombers. They actually fled from the police and fought back. And so, yes, while he was dying in that boat, he did say some things about being ready to die, however, he surrendered.

And so while he may have said certain things about wanting to die, I think his actions make it clear that maybe he didn't want to die. And I wouldn't be surprised if the jury ever speaks if they say that they talked about that fact.

WHITFIELD: So then help us understand where he's held, you know, and what the conditions are like on death row on the federal level for him.

ROBBINS: Well, so what's going to happen is this, right now he's in Massachusetts in a federal prison. He'll be held there until probably August or September because there's a bunch of legal things that need to happen before the judge can sentence him. He's been sentenced to death on six of the 17 death penalty counts but there were 13 other charges that don't carry the death penalty that the judge will need to sentence him on additionally. So after the sentencing, he will be transferred from the U.S. Marshalls to the U.S. Bureau, you know, of Federal Prisons. He'll be moved to Indiana --

WHITFIELD: Terre Haute.

ROBBINS: -- where the federal death penalty prison is and he will be in lockdown 23 hours a day, it's a miserable life. He will get visits mostly from his lawyers, if from anybody. He'll have a brand-new team of lawyers, by the way.

WHITFIELD: Why?

ROBBINS: As soon as the case is filed on appeal -- well, because what you want is you want a fresh set of eyes and these appeals are hugely complicated. And this was a massive case. And so there are death penalty attorneys that specialize, Fred, actually in the appeal process, which is why it's so costly. This is going go on for years. And the first phase will be to question every single ruling of the trial.

If they exhaust all of at peels in that first phase they can then go back and do an entirely second phase of appeals where they argue things like lethal injection is unconstitutional, the death penalty is unconstitutional, things not related to the case. So this could be a decade before they ever execute him, if they do.

WHITFIELD: And this is taxpayer financed, right? Because didn't he have a public defender?

ROBBINS: That's correct. And also, one more thing, Fred, that a lot of people don't realize is that a lot of people say, hey, you know, somebody's convicted in a case like this, just execute them. I don't want to pay for him to rot in prison. Well, the truth is, it costs approximately 10 or 11 times more.

WHITFIELD: Wow.

ROBBINS: To kill somebody than it is to house them for the rest of their lives because of the cost of appeals and because of the cost of putting them on death row.

WHITFIELD: OK. All right. We will leave it right there.

Mel Robbins, thank you so much. Learned a lot. Appreciate it.

ROBBINS: Great to see you.

WHITFIELD: All right. The Defense Department is calling an American special ops raid in Syria a success. We go to the region next to get new information on the key ISIS figure killed in that raid.

(COMMERCIAL BREAK)

[13:31:01] WHITFIELD: All right. Mortgage rates ended the week mixed. Have a look.

(COMMERCIAL BREAK)

WHITFIELD: Hello again, everyone. Thanks so much for joining me. I'm Fredricka Whitfield.

Our top story, a U.S. Special Operations raid overnight in Syria killed a key ISIS figure. U.S. officials tell CNN that the man, Abu Sayyaf, a Tunisian citizen, was the equivalent of ISIS' chief financial officer, also involved in military operations. A source tells CNN that he may have had contact with ISIS leader Abu Bakr al- Baghdadi. Sayyaf's wife also captured in the raid. An official says the commandos also made off with reams of ISIS data.

CNN's Nick Paton Walsh is covering the story for us in the Middle East and has more on this key ISIS leader.

NICK PATON WALSH, CNN SENIOR INTERNATIONAL CORRESPONDENT: Fredricka, the question I think many long term observers of ISIS are asking is quite who was Abu Sayyaf. Now clearly very valuable to the United States. In the statements we're hearing from the Pentagon and from the White House this was a man increasingly in control of military operations, who have valuable communications, who was key to the oil business they used to run where they used to get so much of their money.

But he wasn't really well known. He didn't appear in social media. He wasn't really a name you would immediately latch onto. We don't even know his real name at this stage. Abu Sayyaf just means father of Sayyaf, and his wife, Umm Sayyaf, captured by U.S. Special Forces, it means mother of Sayyaf. So details still to come forwards about that. But also the risk was staggering. No flying into deep ISIS territory here into a heavily fortified oil field, said to have three to five kilometer security perimeter built in around.

So very difficult indeed for those Delta Force commandos. And they were hoping, it seemed initially, to capture this man. And we know that ISIS leadership worshipped death as part of their perverted version of the jihad they're waging. So it would have been an outside chance, frankly, they would have captured him alive and that he'd get his wife. So a lot of questions really about whether he was the original target or perhaps they hoped his telephones, his computers would provide a gateway on to real ISIS leadership targets that the American public are very familiar with.

[13:35:10] Perhaps like Abu Bakr al-Baghdadi who he said to have had communications with, maybe even spokesperson, Muhammad al-Adnani, who we're told he may also have been quite familiar with as well. But a high-risk mission, the kind of mission we've seen in the past used for hostage rescues. No suggestion of that at this particular stage. But indeed one which had it gone wrong, god forbid, it would have been very hard to explain from the White House to the American public why they decided to send American troops in harm's way. But clearly a very valuable individual. They must be going through

whatever intelligence they gathered to try and help it make them better understand the functioning and whereabouts of ISIS leadership but also a definite suggestion that the U.S. is willing to perhaps endure a greater risk in finding ISIS leadership like that. And you have to ask questions really about what may have been the final target they hoped this raid would bring them to or perhaps what this means for future U.S. involvement inside Syria. A very risky mission indeed -- Fredricka.

ANNOUNCER: This is CNN breaking news.

WHITFIELD: All right. Nick Paton Walsh, thank you so much.

More information now on Abu Sayyaf, who is the so-called CFO and we understand also maybe a key component in the hostage operation of ISIS. For that, let's go to CNN's justice reporter, Evan Perez.

So what more do we know, Evan?

EVAN PEREZ, CNN JUSTICE CORRESPONDENT: Well, Fredricka, this is someone that, I'm told, by U.S. officials that was either deeply involved, either deeply involved or knowledgeable about ISIS' hostage taking operation and could provide -- his wife, now that she's in custody, now that she's being interrogated could provide knowledge and information about the treatment of hostages, particularly any Americans that were being held by ISIS in Syria.

Now the FBI's high value interrogation group is expected to conduct that interrogation. Now what they do is they do two types of interrogations. One for intelligence purposes and one is for possible prosecution. That raises the possibility that while she is being held at -- the wife is being held in Iraq right now in military detention, she could perhaps someday face justice in the United States if they can gather enough evidence to bring charges against her.

I'm not sure what citizenship she has, if she can be tried in another country but certainly what the U.S. will try to do, if possible, is to try to bring her to justice in the United States if possible.

WHITFIELD: And so, Evan, what do you know about that type of end of the operation, whether she would be brought to the U.S. or whether the interrogation would continue to take place there on foreign soil, how much more complicated does it get to try to bring her to the U.S.?

PEREZ: Well, you know, it is -- it is complicated. But you know, they've done this type of operation before. They've tended to put them on a ship, military ship, sometimes spend over a week trying to bring them back to the United States. So they've done that before to conduct these type of intelligence interrogations. Again, there's two different types of interrogations they try to do.

And -- but what I think is the importance here, and I think Nick Paton Walsh was hinting at, was the idea that, you know, this is somebody, Abu Sayyaf, in particular, that the American public doesn't know a lot about, has never even heard of, and the importance of him and his files and his wife is such that they wanted to risk American lives to try to capture them and bring them back. Clearly he died in the operation, but it does -- it does point to the importance that the U.S. believes they played in, again, this hostage taking, the hostage movement of hostages and the mistreatment of hostages, perhaps even the beheading of the hostages that we've seen so far that have drawn so much international condemnation of ISIS.

And so again this points to the importance of both the spouse and Abu Sayyaf and the possibility that the U.S. is trying to bring them back to try to make them face justice for what has happened to American hostages in particular.

WHITFIELD: All right. Evan Perez, thank you so much. Great reporting. Get back to us when you have even more.

Let's bring in CNN contributor Michael Weiss and the co-author of the book "ISIS: Inside the Army of Terror."

Good to see you, Michael. So what does this information tell you about now the reach of Abu Sayyaf might be much greater, not just the CFO of operations, the head finance guy, but now may have much more involvement with the capturing of hostages, the holding of hostages by ISIS?

MICHAEL WEISS, CNN CONTRIBUTOR: Well, I mean, what's interesting to me is this may suggest that there's indeed another American hostage or hostages being held by ISIS. So far as I know, so far as been reported and what the U.S. government has disclosed there are none left. ISIS killed them all.

[13:40:10] I do think, though, Abu Sayyaf, I don't -- I really don't believe he was the primary target. I think there were others that were -- Delta Force was trying to go after. In fact just a few minutes ago "The Daily Beast" reported, quoting a senior U.S. official, saying that there were other targets and that some of these were possibly even more high value than Abu Sayyaf himself. It's important to recognize a few weeks ago, the U.S. put out a hit list, a bounty on what they consider to be the top figures in ISIS.

This man's name was nowhere near that list. There wasn't any kind of reward offered for his capture. Now you can say well, that was because they were planning this raid all the time. But it's still very murky and unclear to me why they risked American lives to go after a guy that, to be honest with you, even people inside ISIS had never heard of. I couldn't believe that myself when I put it to a few people in the organization. So I think --

(CROSSTALK)

WHITFIELD: So you're -- and you're saying you talked with people who are either inside ISIS or close enough and you're saying they don't even know who this person is?

WEISS: A few of them in Syria have confirmed like they've never heard of him before. So if he was such a high-ranking figure, the oil emir or the guy -- I've even heard it suggested he's the one responsible for trading the oil back and forth with the Assad regime, that I probably do believe. But again, you know, now all of a sudden he has a role in hostage taking. It was suggested earlier on this morning that despite being in charge of the sort of financial resource operation of ISIS, which by the way the Pentagon itself has said they no longer make the bulk of their money through selling oil, but thanks to degradation of the oil infrastructure through coalition airstrikes, but he had a role in command and control, so a military strategist. It seems like with the passage of each hour this guy becomes more and more prominent and influential.

WHITFIELD: So tell me what you're implying because it sounds you're very skeptical, you're very doubtful of his role.

WEISS: I --

WHITFIELD: Whether he's a valuable target, it almost sounds like you're now questioning the entire operation. So just tell me flat out what are you thinking?

WEISS: Yes, I think -- look, obviously this is a big scout for the Americans, and you know, they -- he obviously was a -- I would say probably a mid-level figure in the ISIS apparatus. But the line that I've heard, which to me seems most plausible, Dr. Hisham al-Hashimi, the foremost Iraqi expert on ISIS, says that Abu Sayyaf, who was close to Abu Muhammad al-Adnani. Nick Paton Walsh referred to him earlier.

He was the official ISIS spokesman but more than that he has seemed to be one of the top contenders to be the caliph or the -- you might call it the caretaker caliph in the event that Abu Bakr al-Baghdadi is killed or rendered incapacitated. So somebody like an Adnani, because his background, I mean, is quite extensive. He goes back to the days of Abu Musab al-Zarqawi, the founder of al Qaeda in Iraq. He has a very long history in the organization. He is very prominent amongst the ISIS because of his official role of the spokesperson or the chief propagandist. He would be somebody I can see them sending Delta Force into that.

WHITFIELD: So do you think that this kind of operation hasn't anyway rattled ISIS even if he is mid-level or as sources are telling CNN that he has a high-ranking operative, you say he's more mid-level, but do you think, nonetheless, the taking out of Abu Sayyaf rattles in any way ISIS?

WEISS: Yes, look, when we say mid-level and high ranking, it's important to understand, within an organization as murky as ISIS, there's a lot of, as we say in the Cold War, Kremlinology being done on who's who, who is up, who is down, you know, who is the number three guy versus the number five guy. I say mid-ranking because no one has -- no analysts of ISIS or scholar of the organization, myself included, and I wrote a book on these guys, had ever really seen this guy as a major figure.

Now that's not to say he doesn't have a rather furtive intelligence portfolio that the United States is aware of. But in terms of rattling ISIS, yes, absolutely, because it shows that they can get -- they can get these guys, sending in elite teams of U.S. Special Forces, in both Syria and in Iraq. This isn't the first time, by the way, special operations have nabbed an al Qaeda in Iraq-slash-ISIS figure in Syria. In 2008 they went and killed a man called Abu Ghadiya. He was the guy at the border responsible for funneling in jihadists from Syria into Iraq for purposes of blowing up U.S. soldiers.

So we've been down this road before. And again the intelligence haul from this operation, I would submit, is likely to be greater in terms of the -- you know, the future conduct of the war.

WHITFIELD: In terms of -- yes. Comparing to the -- yes, that's killing --

(CROSSTALK)

WEISS: Exactly. They always get a great trench of documentation showing the network's communications, you know, conduits and things like that. So that could be another reason that they conducted this raid.

WHITFIELD: All right. All fascinating.

Michael Weiss, thank you so much. Appreciate it.

WEISS: Sure. Thanks.

WHITFIELD: All right. Next, we're going to talk about presidential politics. Former Florida governor Jeb Bush hoping to put this week perhaps behind him. Is he in, is he not? He had a tough time with questions about the Iraq war.

[13:45:12] Next, our political experts debate whether this will hurt him if indeed he officially runs for president.

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WHITFIELD: All right, welcome back. Right now almost the entire Republican presidential field is descending on Iowa, the state that holds the first presidential caucus less than nine months from now. And among those seeking support this weekend is Jeb Bush, who is struggling in the polls there. He held a town hall this morning, in fact, in Dubuque, and this week he also struggled in a major way with a question about the Iraq war.

It took the former Florida governor five days to clarify his position on whether he would have invaded Iraq in 2003, like his older brother, President George W. Bush, did.

[13:50:00]

(BEGIN VIDEO CLIP)

MEGYN KELLY, FOX NEWS ANCHOR: Knowing what we know now, would you have authorized the invasion?