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Clinton Correction Facility Prison Guards Now Under Investigation; Clinton Prison Guard Now Charged With Felony; Why Guards Help Prisoners Escape; Obamacare as Obama's Legacy; Funerals for Emanuel AME Church Shooting; Removing Confederate Symbols from Public Display. Aired 8-9p ET

Aired June 25, 2015 - 20:00   ET


[20:00:08] ANDERSON COOPER, CNN HOST: Hey, good evening. Thanks for joining us.

Yet more new developments tonight in the New York prison break. And later a story with plenty of parallels.

A prison worker falling for a killer and helping him escape. Only this one involved a dog crate not a catwalk and puppy treats and not chopped meat. We'll talk with a dog handler who smuggled her murderous lover out of prison.

We begin, though, tonight in upstate New York where the prison guard who gave killer Richard Matt tools and access to prison catwalk and finally on May 30th delivered the ground beef with the hacksaw blades in it. A meal that Matt's mistress prison tailor Joyce Mitchell cooked up for him.

The guard Gene Palmer has spoken to one of our producers. We will bring you the latest on that. We are also learning even more including what he told New York state police about the favors he did for Matt and David Sweat. And in addition, Mr. Palmer has a new attorney. He has also got a new court date.

And Alexandra Field, she has the very latest on all of it including breaking news, yet one more factor that may have helped Sweat and Matt prepare their escape.

Alexandra, what have you learned?

Good evening, Anderson. CNN learned that investigators are now looking at whether prison guards on the honor block may have been sleeping during their evening shifts which would have potentially allowed Richard Matt and David Sweat to prepare for they escape unsupervised. The inspector general's office launched a full investigation. They have been onsite at the prison. They're trying to determine whether and what extent any prison protocols may have been breached. At the same time, Gene Palmer is speaking to constituent police giving them a look at what was really happening behind bars.


CNN has learned that investigators are now looking at whether prison guards on the honor block may have been sleeping during their evening shift which would have potentially allowed Richard Matt and David Sweat to prepare for their escape unsupervised.

The inspector general's office has launched a full investigation. They have been on site at the prison. They are trying to determine whether and what extent any prison protocols may have been breach. At the same time, Gene Palmer is speaking to state police giving them a look at what was really happening behind bars.


FIELD (voice-over): An official close to the investigation tells CNN that Gene Palmer, a prison guard, gave at least one of the now escaped inmates, a screwdriver and needle nosed pliers supposedly to help fix electrical breakers in the catwalk area behind their cells allowing the two men to scout out their escape route. The tools were later found at Palmer's home after police executed a search warrant. Palmer, supervised Matt and Sweat while they worked on the breakers taking the tools back at the end of his shift.

ANDREW WYLIE, CLINTON COUNTY DISTRICT ATTORNEY: He didn't obviously, you know, come forward and say I received paintings from Matt and Sweat. I provided them with needle nosed pliers. Those are things are obviously that, you know, he did not disclose until he got caught.

FIELD: In an interview with New York state police, Palmer says he didn't realize that the assistance he provided to Matt or Sweat may have made their escape easier. Palmer tells investigator he's gave Matt paint brushes and hamburger meat. In return he says he would receive elaborate paintings and information on illegal acts taking place inside the prison.

According to court documents, Palmer later tried to destroy the paintings by burning some in a fire pit and burying others in nearby woods. In an NPR radio interview from 15 years ago, Palmer describes life inside the Clinton correctional facility as a negative environment. He went on to say that life as a prison guard is as miserable as the lives of the prisoners themselves.

GENE PALMER, PRISON GUARD: With the money that they pay you you'll go bald, you will have high blood pressure, you'll become an alcoholic, you'll divorce and kill yourself.


COOPER: Wow. It is quite a statement.

Alexandra, I want to bring in CNN producer Shimon Prokupecz who spoke recently with Gene Palmer.

Shimon, as I said, you've spoke to Gene Palmer shortly after he had talked to police earlier this week after he had been questioned. What was the state of mind then? SHIMON PROKUPECZ, CNN PRODUCER: He was frightened. Sort of there was

a sense of despair, sort of what did I do? And he felt really, really bad. You could see the pain all over his face. At one point, he started to cry. When he was thinking about his family and sort of what he did. And what life would be like for him now.

You know, this man was a corrections officer for 28 years. He was, you know part, of what he called a law enforcement team. And never did he ever expect something like this to happen and he had no intention for this to happen. And, you know, I sort of felt that, he really sort of, felt that he -- felt betrayed, betrayed by the prisoners, by Matt and Sweat, who he befriended at the jail who were providing him with information, and really, people he felt, you know, were helping him and he was in some ways helping them and there was nothing wrong with that in his mind.

COOPER: Alexandra, what's next for Gene Palmer?

FIELD: Well whatever he thought, whatever he felt, whatever he expressed to investigators, he is still facing some pretty serious charges three felony charges, Anderson. He was scheduled to have an appearance in court this afternoon. He was not there for that. And instead, the hearing was actually postponed until Monday because a new attorney will be taking over this increasingly high profile face.

[20:04:57] COOPER: All right, Alexandra, appreciate the reporting. Shimon as well.

Joining us now is former New York City corrections department deputy warden Ed Gavin and Brian Mann of North County public radio who did that interview with Gene Palmer that you just heard in Alexandra's report.

Brian, I want to start with you. I mean, that interview is fascinating. He was your guide on a story you did, I believe, 15 years ago inside the prison. He showed you the north yard of the prison. And you say that was an area controlled mostly by the inmates where they kept barbecue grills, recreation areas, garden even. It is amazing that this was happening inside a maximum security prison. Did it surprise you?

BRIAN MANN, NORTH COUNTY PUBLIC RADIO: Yes, I was blown away by what I saw. I saw inmates, you know, working with power tools. I saw inmates with an enormous amount of liberty. The gang activity there sets the pace for a lot of the life that goes on behind the big white wall at Dannemora.

It is really important to understand, Anderson, that you know, there are about 3,000 inmates in that facility. And there is sort of a little world in there. The inmates define much of that world. But they also have this relationship with the corrections officers that develops over time. And so, you know, what I saw in there it was literally like walking into a completely different culture, a completely different world where the inmates have far more freedom and also far more control than I ever understood before.

COOPER: I mean, you have done a lot of reporting on the prison system. How common are these types of freedoms that you have seen?

MANN: I think some of it is more common than people understand. For example in correctional facilities all over the United States, it's common for inmates to help do maintenance work. It's common for them to do grounds keeping. So inmates often know a lot more about how a correctional facility operates than, than, you know seems to make sense to people outside. There is also, and this I think is really shocking to people, there is a kind of intimacy that develops between corrections officers, civilian staff, and these inmates. You know, in this case, Gene Palmer was working very closely with these two inmates for a very long time. I mean, Richard Matt moved into that block in 2009.

That means that, you know, he got to know Gene Palmer over a period of many, many years. And slowly, you know, you do develop levels of trust, levels of understanding, and most corrections officers know how to work the gray zone, how to live in that ambiguous place without crossing the bright lines. And Gene Palmer clearly crossed some bright lines here.

COOPER: Ed, I mean, when you hear this about sort of areas that prisoners seem to control and that relationship that clearly existed and grew over time between the people. What do you think?

ED GAVIN, FORMER DEPUTY WARDEN, NEW YORK CITY DEPARTMENT OF CORRECTIONS: I say, Gene Palmer crossed the line. How do you give an inmate a screwdriver with a handle? That could be used as a shank? That is a weapon. He is a convicted killer. His partner is a convicted killer.

COOPER: Not only a convicted killer. A police killer in the case of Sweat and somebody who dismembered --

GAVIN: So worst case scenario on the block, he has a bad day and he has got a screwdriver. You just gave him a shank. He can open you up with that like a can opener.

COOPER: That idea that he gave hamburger meat to this guy without putting it through the metal detector, to you that is simply unbelievable?

GAVIN: I can't believe it, no. There is just no excuse for it. None whatsoever. I have never heard of anything like that where a sworn uniformed member of service would do something like that at the behest of a civilian employee. Like I said he was duty bound from the moment she asked him to do that to report it.

COOPER: As somebody who worked in prisons how do you prevent that relationship from developing? Because clearly it seems like at least in the case of Gene Palmer, he trusted these guys?

GAVIN: That's a personal choice. You have to have integrity. And you have to have your integrity with you. It has to be intact at all times.

COOPER: Brian, in your interview with Palmer, he talked about how closely the guards and inmates collaborate, how they trust each other, that it is all that carefully calibrated system of reward and punishment. I want to play a bit about what he had to say about that system.


PALMER: It works for us, just as the TV's work for us that we have for them in their cells, soap operas, you'd be surprised how stimulating they are for an individual. Yes it does work. "Days of Our Lives."


COOPER: I mean, after seeing all of this, were you surprised the system seems to have failed?

MANN: Here's what I thought was sort of the way that maximum security prisons in New York worked. Is that there were these strange cultural relationships, there were these sort of nuanced negotiated arrangements inside, but that the outer perimeter was rock solid. And what we are seeing with the investigations that are underway at Dannemora now is that slowly over time those protocols, those systems, broke down.

And I think what we are going to see is Joyce Mitchell and Gene Palmer, you know kind of the tip of the spear. There are going to be big questions asked about larger issues of supervision. You know, who was monitoring the behavior of the corrections officers? Were they working the kinds of shifts where they were, you know, some of them were sleeping on duty?

I want to say, Anderson, it is very important to say, corrections officers here in the North Country have an amazing record. Most of them are extraordinarily devoted officers, but, you know what we have seen over the years is there are officers who bring contraband into prisons, there are officers who cross these bright lines. Usually they don't have consequences this dire. This is, this is, you know, code red. But this does happen. People cross these lines.

[20:10:37] COOPER: Ed, I mean, do you believe this is the tip of the iceberg? That there is a lot Mr. That needs to be looked into in this prison?

GAVIN: Absolutely. I mean, when you look at the nexus between Joyce and Gene, both of them received paintings. Both of them brought the paintings home. How many other officers received paintings from these guys? Did Gene provide paintings to other officers? Did they bring in photos of their family? Did these inmate then paint those, you know? Paint pictures for members of service? I think it has to be looked into. I think there is a lot more going on than we are being told.

COOPER: And it is certainly being investigated as we know right now.

Ed Gavin, I appreciate you being with us. Brian Mann, as well.

We have more breaking news ahead. Growing fears that Sweat and Matt now may have of a weapon or weapons.

Plus a survival expert shows house to find the clues the fugitives are leaving and how to use them to track these killers down.

Later the woman who fell for a murder, helped him escape and lived on the lam with him. Her story, we'll talk to her ahead.


[20:15:23] COOPER: There is plenty breaking news tonight about the prison guard Gene Palmer who wittingly or not helped David Sweat and Richard Matt break out. There is also much concern that the two men who are still at large could very well be armed.

Gary Tuchman joins us now from the search zone in Owls Head, New York. So this is the 19th day of the manhunt, I mean, are they any closer to finding the guys or are they pretty much where they were yesterday?

GARY TUCHMAN, CNN CORRESPONDENT: Anderson, unfortunately no sign of the killers as of yet. But they're only increasing the numbers of resources. There are now more than 1,100 federal, state, and local police officers on the scene. And they're mostly patrolling the area here in Owls Head, New York, this tiny town. And Franklin County where Owls Head is located.

One of the issues they face right now, these police officers, is they know there could be a violent ending. There is absolutely that possibility. So what's happening right now these officers are looking at a lot of cabins there in the woods? There are hundreds of cabins in the woods here. Most are empty. There are two reasons for that. Number one, because this is not the peak of the hunting season and number two many people who own the cabins aren't coming down because of what is going on.

Now what happens with a lot of the cabins is weapons are left behind. Hunting guns over the winter. But the cabins are locked. But the hunting guns are left there. They're called camp guns. And the idea is they come for the hunting season, their guns are ready to go. And that's the concern among many police officers here because they feel if the two killers didn't get weapons in the cabins where their DNA was found but they may have broken into another cabin and therefore have weapons.

You talk to 100 police officers, it would be hard to find one here who doubts that these guys are armed. And this town has completely changed, Owls Head, because what is happening, this is the kind of place Anderson you go and people leave their doors open. They don't just leave them unlocked. They leave them open at night on warm summer evenings. That is not happening now. They're locking their doors. And many of the people who remain behind are armed.

COOPER: No, understandably. Gary, appreciate it.

In a moment, you are going to see up close the kind of trail that anybody might leave in the woods. But these killers might be leaving in the woods without even knowing it. But first, I want to go next to one of the lead searchers, Kevin Mulverhill, is sheriff for Franklin County where the manhunt is focused. He joins us now.

Sheriff, appreciate you booing with us. First of all, what can you tell us about where things stand now? Have you had any credible sightings or leads?

SHERIFF KEVIN MULVERHILL, FRANKLIN COUNTY, NEW YORK: No, the only credible sighting we had was the sighting Saturday at the cabin where the DNA was located. We had a number of sightings we have run, just to nothing, either they were, they weren't the people we were looking for or there was just nothing there.

COOPER: Can you just describe, I mean, the difficulties in searching? I think if somebody hasn't spent time in the outdoors in the woods they might not get a sense of just how tough this can be no matter how many people you have?

MULVERHILL: Well, we have a couple of issues. One it is such a vast area, you know. We are here in the northern end of the Adirondack Park. The foliage is extremely thick. We have had some heavy rains come through here recently. And like I say it is just extremely thick. It is difficult to walk through. And you know it's hilly, mountain territory. And if that is not hilly, and mountainous, it is swampy and wet. So it is difficult area to traverse.

COOPER: How do you make sure if, you know, people talk about creating a perimeter and moving in, how do you make sure that somebody isn't able to go back to an area, you know, one of these guys isn't able to go back to an area that you have already searched in? I mean, that would be an extremely difficult thing to prevent.

MULVERHILL: Absolutely, it is difficult to prevent. You know, we will go back over those if need be. We are getting a lot of tips from the public. None that have been credible thus far. But I mean, we are getting help. We get a lot of phone calls. Some of them from actual outside the perimeter. So we are, you know, we are ensuring that we still believe they're within the perimeter. But we are checking all the leads, everything that comes in is getting a really good look at.

COOPER: Do you know one way or another whether Matt and Sweat are armed at this point? I mean, were there guns in the cabin that you know they broke into?

MULVERHILL: No guns that we are aware of. Let's face it. They're convicted killers. They have committed homicides in the past. They're intelligent men. They broke out of maximum security prison. We believe that if they had the opportunity to arm themselves they did.

COOPER: I talked to some people who have conducted manhunts in the past. You talk about the need to kind of pace the search out. How do you, how do you do that? Because when it has been going on for as long as it has been going on, how do you keep people from just getting exhausted? I mean, obviously there is a lot of people out there who want to find them and working 'round-the-clock to do that? [20:20:02] MULVERHILL: Right. It's been, I tell you, it's been great

as far as being able to relieve and keep the fatigue factor down, you know. We are going in as teams. Those teams are coming out. They have rested. We are hydrating them. We are keeping them well hydrated. The police, law enforcement, generally are going in three, four day shifts and completely switching out. So it, we're keeping our fatigue factor down which actually works to our advantage because they don't have that opportunity.

COOPER: Well, sheriff, I certainly hope you guys find these guys quickly as soon as possible. Appreciate all your efforts. And thanks for talking to us tonight, Sheriff Mulverhill.

For several days now, we have been getting advice from the expert on what it takes to survive on the run in the wild and to track somebody who is on the run. That expert has been with us on the set. Today he took his knowledge outdoors along with CNN's Rosa Flores.


SHANE HOBEL, THE MOUNTAIN SCOUT SURVIVAL SCHOOL: There is so much out here wants to stick you, poke you, sting you, bite you.

ROSA FLORES, CNN CORRESPONDENT (voice-over): Shane Hobel is a survival and tracking trainer, meaning he teaches people how to live off the land and how to track down just about anything traveling through a forest. He is closely watching the manhunt in upstate New York. These escapees are not survivalists that we know of.

HOBEL: Right.

FLORES: So what would they be doing?

HOBEL: Well, you know, the number one rule its shelter. You got to get out of the elements.

FLORES: Aside from breaking into cabins for shelter and food, Shane says the escapees could be bundling under a pile of leaves to stay warm at night. But wouldn't be savvy enough to do much more. That is very noisy if you are trying to hide from authorities you wouldn't want to do that.

HOBEL: Correct.

FLORES: Meaning what keeps them warm could be a huge clue for search teams. In fact, Shane says their every move could give up their position if a trained eye, like his, could follow their tracks. For example, take a close look at this area. It could look like nothing to an untrained eye.

HOBEL: Immediately things are already popping out to me.

FLORES: Like what?

HOBEL: So I already know there is tracks, I know that there is a track right here. This has been pushed down. This group right here, and this group has been pushed forward. Look at the color - and as the foot left it lifted the stick and pushed this into its place. Because this is clearly not, natural behavior. This now how this plant was growing.

FLORES: Shane says this would technically be called a run. A series of signs showing someone ran through the woods. But not every clue is left on the ground. Shane also looks for clues at shoulder level.

HOBEL: If I moved here, swiftly or a bit more with aggressive, aggressive behavior, I may have moved it in such a way that it did grab itself. And this is the type of thing that we'll look for. It's the thing that doesn't make sense out here.

FLORES: Even if authorities trace every track, the disturbance on greenery down below or even branches up above, there is one other complicating factor. And that's the weather. Severe rain could erase tracks left behind.

HOBEL: Rain has a tendency to wash tracks away completely.

FLORES: The recent heavy rains in the area could help escapees stay one step ahead of authorities. But Shane says, it is only a matter of time before they become desperate and make a mistake.

Rosa Flores, CNN, New York.


COOPER: Fascinating to see the little clues.

Just ahead, a prison escape foreshadowed this one in so many ways. We are going to talk to a woman, a dog handler, who got a bad case of puppy love for a killer then smuggled him out of prison in a dog crate.

Later, solemn moments remembering the victims of the Charleston church shooting, as President Obama prepares to eulogize the senior pastor tomorrow.


[20:27:55] COOPER: Well, as wildly strange as the Joyce Mitchell, David Sweat, Richard Matt, Gene Palmer, hamburger helper as sad it sound and is, there is one thing that is not. It is not unique. Ground beef and hacksaw blades might set it apart or access for oil paintings and reports of tailor-made sex in stored closet.

That said, many others have fallen for inmates and some have escaped and done some ways that rival what happened at Clinton. Ten years ago, Toby Dorr was working at the Lansing correctional facility in Kansas. She was running a program that brought in rescue dogs for the inmates to train. That's when she fell for convicted killer John Maynard, and a few months later struggled him out of the prison in one of her dog crate. Dorr who served the 27 months sentence for her role joins us now. Toby, thank you so much for being us. I think a lot of people who

look at Joyce Mitchell wonder how somebody can get to a place where she helped somebody escape from prison. I wonder how it happened for you. What was it that this guy did or said that created that connection between the two of you?

TOBY DORR, HELPED JAILHOUSE LOVER ESCAPE IN DOG CRATE: Well, first of all, I think a woman has to be at a point where she is pretty broken and she is in a desperate state. And when you are in that state, things that normally seem ridiculous don't seem so far-fetched. So in my instance, I was working really hard. I had a lifetime where I worked really hard and performed at a high level. And I, I just felt this tremendous pressure to always be on and be my best for everybody and everything that I did. And I reached a breaking point. And in my case, I happened to reach the breaking point just at the same time that an inmate took notice of me. And told me how nice I looked. And acted like he cared about what kind of a mood I was in on that particular day.

COOPER: Was he somebody - sorry, was he somebody who kid of you felt listen to you or notice things about you and other people in your life didn't?

DORR: Yes, exactly. And we would spent a lot of time talking. And it was just, you know, human beings want to have a connection with somebody. And when you have someone who just spends a lot of time talking to you and telling you things about you that you like to hear it's kind of just like pouring water on a dying plant.

COOPER: I know he sort of became your protector. There was an incident where somebody threatened you. And he stepped in. He became your escort around the prison. Did --

DORR: Yes.

COOPER: I have talked to some experts who say that often it starts with something small. Like a small, will you do me a favor? It's kind of a baby step. And you, you kind of end up on this journey that you never thought you would end up being on.

DORR: Yes, exactly. And I think, you know anything in our life I think starts with baby steps. Just like that. But in my case it was someone stuck up for me, and kept me from being physically accosted by an inmate. I felt in fear at that time. So, it did kind of change the flavor of everything. But I do believe that if I had been at a point where I was strong, and courageous, and not so broken, not so desperate as I was, that it wouldn't have mattered. It wouldn't have happened.

COOPER: I know you took money out, I think, of your bank account or savings policy that you had. You bought a vehicle, an escape vehicle. Did it seem real even the day you were driving to the prison to help him break out, did it seem like something this was really going to happen?

DORR: No. It never seemed like it was going to happen. I still sometimes can't believe it did happen. The whole time, you know, we were talking about it, it was kind of like a game. Like well what if this happened? And what if this happened? And I never really believed it. Until even the minute I was driving through the gate I didn't think it was happening. But once I got outside the gate and he was in the van, then it was real. And I was just stunned. I can't look back and see a path I took that got me to that point. It just seemed like I was just there.

COOPER: Did he come up with the plan? Is he the one who proposed the plan? And I'm wondering when he first proposed it what did you think?

DORR: Well, he was - it was his idea. And when he first proposed it, I just laughed, and said, sure, yeah, that sounds like a great idea. But I never -- I never believed it was going to happen. I never -- thought that that was something that was going to be real.

COOPER: And you --

DORR: And it was.

COOPER: And you must have had an idea of what the relationship would be like. I know you spent 12 days with him on the run, I think you were holed up, and - I don't know if you were in a cabin or on a location. What were those 12 days like? Was it as you anticipated it would be like?

DORR: In some ways it was. And in some ways it wasn't. It was kind of an artificial situation because, you know, it just wasn't a normal situation. So there was some things that were fun and good. And some things that were scary and --

COOPER: And I know - I mean as I said, you both were caught. You ended up serving 27 months. I think he got an additional ten years tacked on to his sentence.

DORR: Yes.

COOPER: I'm wondering, have you - and you changed your life. You have gone back to school. You have -- you have got divorced. You've remarried. You are clearly, you know, on a different path than you were. Have you talked to him since the escape? Do you think about him?

DORR: Well, the difference was when I had a relationship with John Maynard he was a person that I got to know very well. And so a lot of things that I think about I do think about sometimes what his opinion would be of something. But I think today I am a lot stronger person. And a lot more courageous. I think I have grown. And we have started a nonprofit ministry where we mentor people getting out of prison and try to counsel them into making the right decisions. I have gone back to school and gotten a master's degree, I have opened two businesses. So, I try to move forward with my life. And I try to -- do what I can to help other people. And one of the reasons why I have agreed to all these interviews is because, I feel like if I had spoken up two years ago, maybe Joyce Mitchell would have heard me. And maybe it would have had an impact on what happened in New York. And maybe not. And if it's not Joyce Mitchell that heard me.

COOPER: What would you say to another Joyce Mitchell who may be out there right now?

DORR: You know, maybe somebody else would. I would say - that this isn't the kind of change you want to make in your life. This is a change that is going to be forced upon you. And it is going to be difficult. And the price is very high.


DORR: If you go in this direction, the price that you have to pay for your decision is a very high price. And it's a difficult one to pay. And -- what I would say is -- look at what things are not right in your life and come up with a different way to change them to do something different with your life. And for Joyce who's already made this decision and is in this position, I would say -- move forward. You know, work on healing the things that are obviously broken in you. So that you can be a stronger woman. And learn to be the kind of person that you have the potential to be. And don't let yourself be defined by this one act. You know, move past it.

COOPER: Well, Toby, I appreciate you talking about this. I know it is not easy. It can't be easy. And I do hope it helps somebody out there. Toby Dorr. Thank you so much.

DORR: Thank you.

COOPER: Well, coming up a victory for the president. The Supreme Court rules on a major provision of Obamacare. We'll take a look at what today's ruling is going to mean for his administration and legacy next.



COOPER: Well, major victory for Obamacare today from the Supreme Court in a six to three decision. The high court ruled in favor of the Affordable Care Act by upholding subsidies for more than 6 million Americans. In a statement in the Rose Garden President Obama said the law is working exactly as it is supposed to.


BARACK OBAMA, PRESIDENT OF THE UNITED STATES OF AMERICA: After multiple challenges to this law before the Supreme Court, the Affordable Care Act is here to stay. This morning the court upheld the critical part of this law. The part that has made it easier for Americans to afford health insurance regardless of where you live. If the partisan challenge to this law had succeeded millions of Americans would have had thousands of dollars' worth of tax credits taken from them. For many insurance would have become unaffordable again.

(END VIDEO CLIP) COOPER: Today's ruling isn't exactly the final word on Obamacare, there are still a number of legal challenges working their way through the court system, but it does represent a huge victory of the president and a step toward preserving what may be the Obama administration's biggest legacy. Joining me now is CNN senior legal analyst Jeffrey Toobin, and presidential historian Douglas Brinkley. You weren't necessarily surprised by it. But I mean, it is a huge victory for the president and for the legacy of the president?

JEFFREY TOOBIN, CNN CORRESPONDENT: Best day for this administration since he was re-elected, maybe the best day since the death of Osama bin Laden. This puts him in a different category from Jimmy Carter, from Bill Clinton. He is someone who will have a legislative legacy that's going to go on for decades and really change the way people live in the country.

COOPER: Can this be reversed?

TOOBIN: Not by the courts at this point. I mean there are parts of it that can be chipped away. It, of course, can be overturned if Congress just tries to pass a law repealing it or putting some other law in. And that, of course, is part of why we have elections in this country. But, as a legal matter, Obamacare is now settled.

COOPER: Doug, it is remarkable that Obamacare was at first used as a really kind of pejorative, but twice now it has gone to the Supreme Court, twice it survived. I mean if that name, it is kind of a badge of honor now for the administration. They use it.

DOUGH BRINKLEY, PRESIDENTIAL HISTORIAN: Well, absolutely. I was doing the magazine profile of President Obama, you know, back when he was running for re-election. And they were unsure whether Obamacare, they should use the language. But then the president grabbed the hold of it, said I will own it. If it means helping people with heart disease, and cancer, and putting millions of people unable to go to hospitals and get medical attention, I will own Obamacare. And think of it, Anderson, I mean people don't talk about Social Security, as being FDR care, Medicaid, and Medicare, as LBJ care or something. So this is going to live for a very long time. And I agree with Jeffrey, it is I think, his signature achievement as president.

COOPER: Justice Scalia said today, it might as well call it Scotus care. Using the terminology for the Supreme Court. Obviously, he was saying that not in a positive way. The ruling, the fact that it was 6-3. That surprised you?

TOOBIN: It did. I thought Justice Kennedy who voted that the law was unconstitutional three years ago, the fact that he joined Chief Justice Roberts and the four liberals, did surprise me. And the breadth of Chief Justice Roberts' opinion. The way he - he didn't just say, well, President Obama's interpretation is OK for him. But another president could come in and change it. He didn't say that. He said the law requires that the subsidies be available in all 50 states. So the breadth of the victory did surprise me. And just how definitive it was. COOPER: Doug, do you think Chief Justice Roberts approaches these

kinds of cases with his own legacy in mind? The current court is known as the Roberts' court. He is the face of that court.

BRINKLEY: No, I don't think he does, I don't think it's anything to do with legacy. I think he did what was right and what he thought was the most important thing.

COOPER: Now, I actually disagree with that. I think Chief Justice Roberts does think about his legacy and you know, each chief justice has issues that they care about, a lot. And I think Chief Justice Roberts cares about getting rid of racial preferences. That, that's something that he is really embraced as something that he wants to get done. This was a very much a one off case. It wasn't even involving the Constitution. All it involved was the interpretation of four words in one statute. And I don't think Chief Justice Roberts wanted his court to be known as the court that took health insurance away from 6.5 million people.

COOPER: There are a number of huge cases still to be determined by the court. Legalization of same-sex marriage. When do you expect -- when are you looking at that?

TOOBIN: Well, the court says they will issue decisions tomorrow at 10:00, and Monday at 10:00. Although they could add another day. I think there are five decisions outstanding, by far the most important of which is same-sex marriage. So, I think 10:00 tomorrow or 10:00 Monday is likely for that decision.

COOPER: OK, Jeff Toobin, thanks very much. Doug Brinkley as well. On the president's schedule for tomorrow, a solemn and said occasion.


COOPER: He's scheduled to give the eulogy at the funeral for Reverend Clementa Pinckney gunned down along with eight others at a Bible study just over a week ago. We'll have a report from Charleston next.


COOPER: In Charleston, South Carolina today Ethel Lance's grandson said she was a victim of hate, but can be a symbol of love. Mourners gathered for Lance's funeral today. She was among nine killed in the gun attack at a Bible study eight days ago. Lance was 70 years old.

Another funeral today for the reverend Sharonda Coleman-Singleton. Her son described her as a woman who loved everybody with all her heart. President Obama will deliver the eulogy tomorrow for state senator, Reverend Clementa Pinckney. His wake began just a short time ago, at the same church where the attack took place. Alina Machado joins us now from Charleston. You are outside the church. People have been lining up to view Reverend Pinckney all day. What is the mood like there tonight?

ALINA MACHADO, CNN CORRESPONDENT: Well, Anderson, as you can expect, as you would imagine, the mood here is incredibly somber. It is one of remembering those nine lives that were lost here. This viewing was supposed to be over at 8:00 Eastern. But this is why it is still going on right now. Take a look at this line. This line actually goes down the street and around the building over there. There are hundreds of people who are waiting right now, still waiting to see Reverend Pinckney's casket. Reverend Pinckney's body right now.


MACHADO: This is a spirit of this place here. Love. What happened here a little over a week ago was all about hate. But what we have been seeing here in Charleston, Anderson, is all about love right now.

COOPER: I understand the killer's family released another statement today, what did they say?

MACHADO: The killer's family released a statement from their attorney, through their attorney basically saying that they know that there are still many questions behind the story. Leading up to what happened here a week ago. In the statement they said they feel it is inappropriate for them though to say anything else right now other than that they are truly sorry for the loss that these families are experiencing. They want the focus right now to remain on these victims and their grieving families.

COOPER: And what do we know about the funeral for Reverend Pinckney tomorrow?

MACHADO: Well, we know that a large bipartisan delegation from Washington is expected to come to Charleston tomorrow. We know the president will be here. The vice president. The first lady. And President Obama has been working on this eulogy himself. We know that its focus is expected to be primarily on the nine lives that were lost here last week. But the White House has not ruled out the possibility that perhaps the president could address some of those controversial issues that have come to the forefront since the tragedy.

COOPER: Alina Machado, it's good to have you there. Thanks for being with us tonight. Just over one week after the massacre at Mother Emanuel, there are growing efforts in South Carolina and across the country to remove the Confederate Flag from official displays, also store shelves. The backlash against Confederate symbols doesn't end with flags, though. Barbara Starr reports.


BARBARA STARR, CNN CORRESPONDENT: Thousands of troops that fought across Iraq and Afghanistan shipped out from here, Fort Bragg North Carolina, home of the elite 82nd Airborne Division. Fort Bragg paratroopers jumped into Normandy on D-Day. The first parachute unit trained here for World War II, but despite that glorious history there is a more dubious past. Fort Bragg is named after Confederate Civil War General Braxton Bragg. Fort Bragg is one of ten Army bases across the South the Pentagon says were named for Confederate Civil War generals decades ago as a gesture of reconciliation to a defeated South. LT. GEN. MARK HERTLING (RET.), CNN MILITARY ANALYST: These are things

that were part of a different time, it was part of building a nation. Unfortunately, we had this great Civil War. But these men who were the military leaders were for the most part very good tactician and strategists.

STARR: Well, maybe not, General Bragg.

HERTLING: He graduated very far down in his class at West Point. I think it was somewhere in the 40s, out of total of 52 in the class. So, he was not the brightest of bulbs.

STARR: And amid the current controversy over the Confederate Flag, some lawmakers now believe military tradition isn't enough to keep the names in place.

REP. HAKEEM JEFFRIES (D) NEW YORK: There is a moment now to have a discussion related to the specific military installations and whether it is appropriate for those installations to be named after individuals who were fighting to uphold the institution of slavery.

STARR: Consider Fort Gordon, Georgia named for Lieutenant General John B. Gordon, a top general in the Confederate Army. At the age of 33, he led his forces in a formal surrender at Appomattox. He was widely considered to be the head of the Ku Klux Klan in Georgia. Today Fort Gordon, home to Army intelligence, cyber and communications operations.

REP. SHEILA JACKSON-LEE (D) TEXAS: In fact, the naming of these bases, these forts, were named mostly in the 20th century. In a very segregated South, standing on the shoulders of Jim Crow.

STARR: Fort Pickett, Virginia, now a national cart base, named after Major General George Pickett. In 1863 at Gettysburg he led the assault known as Pickett's charge. Over 6,000 Confederate soldiers died. It would be the last Confederate charge to the North. For some, just fighting for the South makes Pickett a traitor. But for others it's all part of history.


STARR: The Army says it has no plans to rename any of its bases. Today's Army is 20 percent African-American. The largest of all the services. Barbara Starr, CNN, the Pentagon.

COOPER: Well, just ahead we'll have more on the breaking news tonight about prison guard Gene Palmer and the question of whether guards at Dannemora were asleep on the job.


COOPER: Tonight, we are following breaking news on several fronts in the search for escaped killers, David Sweat and Richard Matt. The investigation now focusing on whether guards were sleeping on the job when the inmates escaped 19 days ago. I want to check back with Alexandra Field who's on the ground in upstate New York. The fact that the evening guards in the honor block could have contributed to the escape. What are you learning about that?

ALEXANDRA FIELD, CNN CORRESPONDENT: Yeah, it's a question that the inspector general's office will have to ask. They're doing a wide ranging investigation at the prison to see what kind of protocol may have been breached. But Anderson, it boggles the mind to think that these prisoners could have cut through the steel wall and their cells, cut through the steam pipes, shimmied out through a manhole cover without any detection. But if investigators find that the corrections officers were sleeping in the honor guard during the evening shift, well then it would logically follow that these inmates were left unsupervised for significant periods of time perhaps over a significant period of time.

COOPER: And there is more information about what Gene Palmer gave Sweat and Matt before their escape, right?

FIELD: Yeah, he is facing some pretty serious charges. But he is speaking candidly to state police investigators. He said that there were trades happening in prison. That he was given paintings by them and information about potentially illegal activities. In exchange he gave them certain kinds of assistance, paint, paint brushes, hamburger meat and access to an electrical box in the catwalk - things that he thought were innocuous and now seem not to be, Anderson.

COOPER: Yeah, we know there were tools in that hamburger meat. Alexandra Field, I appreciate the reporting. That does it for us tonight. We appreciate you watching. We are going to be back again at 11 p.m. Eastern for another edition of "360."


COOPER: We'll have all the latest on the prisoners who are still out there somewhere, and the haunt is still on for them. The CNN original series, "The '70s" starts now.