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Tiffany Hanssen: This is All Of It. I'm Tiffany Hanssen in for Alison Stewart. Thanks for spending part of your day with us. Whether you're listening on the radio, live streaming, or on demand, I'm grateful you are here. On today's show, we will talk about a new play, How to Defend Yourself. We'll look at the graphic design legacy of Milton Glazer, and we'll speak with author Matt Ruff about his latest novel, The Destroyer of Worlds. That's the plan. Let's get started with Sin Eater.

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For all of its flashing lights, glamor, and beauty, Hollywood has always had a dark side. The rich and powerful have been shielded from reproach for years. Whether it was during the studio era, golden days, Harvey Weinstein's casting couch, even Trump's groping, we have, if you have enough money, bad behavior could disappear. Of course, it's not just Hollywood. See the Murdochs, but for this segment and for our purposes today, we will stick to Hollywood. This kind of damage control, well, takes a village of well-paid fixers, lawyers, private eyes, informants, and questionable witnesses are all kept on the payroll to protect reputations, investments, and keep those in power, in power.

Before the internet, smartphones, and social media was a lot easier to make things go away. Not everybody was walking around with a camera, documenting things to their followers. Big stars, powerful executives, could just make a few calls and could force someone to settle a nasty divorce, keep a criminal case from coming forward, discredit someone from accusing a celebrity of bad behavior.

In the '80s and '90s, the most well-known and well-paid fixer was Anthony Pellicano. A new two-part documentary from The New York Times sheds light on Pellicano and the antics he used to intimidate, discredit, and disparage anyone who spoke out against his clients, as well as how he used information as leverage to stay in business. It's called Sin Eater. It's airing on Hulu FX. Reporter Liz Day, who led the team that detailed Britney Spears's conservatorship case also worked on this series and is here today. Liz, welcome back to All Of It. Liz is maybe muted possibly.

Liz Day: Hi. Thank you for having me.

Tiffany Hanssen: There she is.

Liz Day: Sorry about that.

Tiffany Hanssen: I see your lips moving. There you are. Anthony Pellicano was just, not just, but he was released from jail. We said this before, he's talking. Is that really the only reason you decided to do this now or is there some other reason that you thought this is the right time to do this?

Liz Day: Yes. We wanted to do this documentary. Even though it's about a scandal that happened around 20 years ago, its lessons are really timeless. As you see in the documentary, a lot of the big, important questions that we explore about justice in Hollywood and accountability for the powerful are really the same questions that are very relevant today.

Tiffany Hanssen: I wonder what it is, just asking you to speculate a little bit, what is it about Hollywood, the ecosystem there, that allows this misogyny and power-hungry cash grabs and all of it to just continue to exist? What is it about the ecosystem of Hollywood that makes it-- Is it special? Not really.

Liz Day: Yes, in some ways, it's special, and in other ways, it has similar parallels to any industry like Wall Street or technology or any other industry. I think there's--

Tiffany Hanssen: Politics.

Liz Day: Politics, that's a good one. I think there's a few things about Hollywood that really let someone like Anthony Pellicano flourish. I think the stakes are really high. We talk about this in the documentary, especially back during Pellicano's period. There's a lot of money sloshing around in Hollywood. If you were at the top, you really wanted to keep your power, and you would do anything to take down anyone who was threatening you. We heard that from the lawyers who employed Pellicano. They said, "We will win at any cost."

Tiffany Hanssen: I just want to go into a little bit how you pulled this whole thing together. You're thinking about him and his impact on Hollywood and all of the clients he worked for, so was this entire project contingent upon getting him to sit down with you? Was that always part of the plan? What was your process?

Liz Day: We first decided upon the idea because a team of us, including my colleague Rachel Abrams, who you see in the documentary, had seen headlines in variety about how Pellicano had been released from prison and was back working for billionaires and other Hollywood power players. We all thought, "That Pellicano story, has that ever been explored in a documentary before?" We all had hazy memories of this being a big deal in Hollywood. It felt like a really big moment in which there may have been a reckoning about how lawyers oversee their private investigators and about how celebrities sometimes bend the rules to get justice.

We thought, "This would make for a really good documentary, let's do it." I think we decided we were going to do it regardless of whether or not we could get him to participate, but that being said, we ideally wanted him to participate. We always want the subject of a documentary to sit down and tell viewers their perspective and share their point of view.

Tiffany Hanssen: What about these clips that you got that no one has these recordings that you had access to? How did you come across all of that? What was the shoe leather you had to put in there?

Liz Day: Yes. We obtained nearly the entire FBI case file on the Pellicano case, which was a real treasure trove. We interviewed a reporter named Allison Hope Weiner, who had covered the story back then for the Times. She was the one who obtained all of this material. Most notably, there are hundreds and hundreds of hours of recordings that Pellicano made of his own phone calls with clients. Sometimes these are mundane, him calling Circuit City about [crosstalk]

Tiffany Hanssen: Oh, this sounds very Nixon.

Liz Day: Yes. He actually told us. He pointed out this interview. It was LBJ who-

Tiffany Hanssen: Oh, there you go.

Liz Day: -pioneered this recording system. Yes, he said, "I did this because I would sometimes forget. I had so much work going on.

Tiffany Hanssen: Oh, sure.

Liz Day: It was just easier for me to record my calls." Ultimately, that was his downfall. One of the prosecutors said he was the biggest informant in his own case because he recorded these calls. On these calls, you really get a behind-the-scenes view of how his clients talk to him and these lawyers, what they asked him to do. One example we cover in the documentary is Pellicano is having this really excruciatingly detailed conversation with Chris Rock, in which they're going over a police report from a woman who has accused Rock of sexual assault.

You hear Pellicano and Rock rehearse their story and Pellicano discusses how he wants to blacken this girl up, the accuser. You really get an intimate view of how Pellicano got people "justice."

Tiffany Hanssen: That's so interesting. For many reasons, but the first one that comes to my mind is what sort of behavior people are willing to swallow in order to maintain whatever status they have. I'm sure you saw that over and over again with him.

Liz Day: Yes. We also played devil's advocate amongst ourselves and said, "If we were Chris Rock, who maintained that this was a false claim of sexual assault against him, if you felt that you were being falsely accused of something that could ruin your career and really ruin your life, would you hire Anthony Pellicano to make this go away and solve your problem for you?" I think that's a really interesting question. Ultimately though, if you do say yes to that question, you have to reckon with how much power you're putting in one individual like Anthony Pellicano to decide where is that line and how much of the rules do you bend if you think you're getting justice in the end.

Tiffany Hanssen: Well, and I think there's just the notion that, "I'm aligning myself with someone who's clearly operating on the fringes just to--" Anyway, you talked about how he speaks in these tapes and I want to talk a little bit about how he spoke to you. I want to play a clip that we have, and then I'm going to ask you about it.

Liz Day: What was your first-time wiretapping?

Anthony Pellicano: I was wiretapping in the '60s.

Liz Day: What made you decide to do that? It's risky, right? It's illegal.

Anthony Pellicano: Oh, honey, it's a minor part of risk.

Liz Day: Were there things that you did that were illegal that the government never was able to charge you with?

Anthony Pellicano: Oh my goodness. Let's see. We're on a tape-recorded interview and you're asking me, "Did I do anything illegal?" Of course, I did.

Tiffany Hanssen: There's a lot to unpack there, but the first thing I want to get to is just him calling you, honey. Did you prepare yourself going into this knowing the misogyny you are going to come up against. He also says at one point something like, "I always like looking at a pretty girl," something like that or, "I'm happy to sit here and look at a pretty girl," or something like that. I'm just wondering, A, did it surprise you? B, did you prep yourself going in?

Liz Day: That's an interesting question. I cringed listening to that and not because-- To be honest, it's not as if I'm offended if someone calls me honey, that's fine, I don't care. Let's just talk about the facts and let's ask you hard questions and let's hear your answers. I do think it does show that Pellicano is from a different era, and he is quite proud about that. He speaks in the documentary about when he gets out of prison, he was disgusted with the way society had changed. We were all crybabies and no one was proud of their country and blah, blah, blah.

Ultimately, we allowed him to pontificate about that a little bit but we don't really care about that. That's not what's important. What's important is, how he operated, who he worked for, and what accountability the entire system had for using him.

Tiffany Hanssen: Well, the other part of that clip that's interesting is that he says he's not willing to incriminate himself and yet, it seems a little curious to me because he's also really willing to brag about stuff that he's the big man on campus. Obviously, he doesn't want to get himself in any more legal trouble but I'm curious how you solve that play out in your conversations with him, he's wrestling with wanting to appear like the big guy.

Liz Day: Interviewing Pellicano was very, very interesting because he sat there and he was asked hard questions and he gave answers, but really, the truth is very elusive with him. One example of that is his relationship with Michael Jackson. We asked him, "Do you think Jackson was innocent of child sexual abuse allegations?" He really wanted to have it both ways. He insinuated to us that he believed that Jackson had molested children, but at the same time, he was adamant that the specific examples of boys in the cases that Pellicano worked on, we're making it up and we're not telling the truth.

For background for viewers who haven't watched the documentary yet, Pellicano worked for Jackson in quiting the early sexual abuse allegations. He ends up mysteriously leaving the case and we asked Pelicano, "What happened? Did you resign? Did he fire you?" There's all sorts of rumors every which way about what happened. Pelicano just would not reveal what happened. He wanted us to believe that he had discovered what he called the truth about Jackson, which made him resign but he wouldn't tell us what that truth was.

We said, "Pellicano, why? Why are you holding on to this mysterious truth? No matter what the truth is, it could help people understand what actually happened," and he still wouldn't go there.

Tiffany Hanssen: You mentioned Chris Rock, Michael Jackson, who are the others? Who are some others that people would recognize?

Liz Day: Pellicano really became famous from the John DeLorean case, who was the famous car manufacturer. He also worked for Farrah Fawcett. He was involved in the O. J. Simpson case. He bragged about working for the Clintons on the Monica Lewinsky case, though exactly what he did, we don't totally know. Then there are just lots and lots of more cases that no one will ever know about because he doesn't want to reveal what he did and who he worked for.

Tiffany Hanssen: We throw around this term fixer a lot. Actually, we've been hearing it a lot in terms of Michael Cohen, Trump's "fixer." You've sat through these interviews now, how do you define fixer based on what you've heard here and what's the skill set for that?

Liz Day: That's another really good question because Pellicano was a private investigator and when he got convicted of these crimes he lost his private investigator license. Now that he's out of prison, he's back working as a fixer. It turns out that fixer doesn't really appear to have a legal definition that we're aware of. It's just a problem solver and that can be anything from someone who just calls up your legal adversary and mediates on your behalf to someone who does God knows what in order to make someone stay quiet and go away.

Tiffany Hanssen: It's interesting, in this digital age, much different than when he was really out there before prison. I mean, a lot of what you're saying sounds to me like a good PR team, plus the willingness to do the unsavory. Our PR teams, our PR firms, I'm thinking after the slap at the Oscars, that Will Smith's PR team was probably in overdrive. Are they the equivalent of the modern-day fixer and that's why the type of person that Pellicano is phased out in Hollywood at this point? Is he, or are they?

Liz Day: No, I don't think so at all. When we called up private investigators and other experts on the industry and we asked, "Are people still doing what Anthony Pellicano was doing?" They all laughed and said, "Yes, of course."

Tiffany Hanssen: Interesting.

Liz Day: They're not wiretapping landlines anymore because no one does that. Certainly, there have been recorded examples of ways in which journalists' phones have been compromised or all other ways that people have been hacked. I think another important distinction between what Pellicano was doing and just a smart, savvy PR team, that Pellicano was intimidating and threatening people. We interview a lot of those victims in the documentary who forever have been changed by that invasion of privacy. They're looking over their shoulders, they're never really the same because of what they experienced at his hands.

Tiffany Hanssen: I want to play another clip here and then we can talk about it.

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Speaker: When agents searched Pellicano's office, they found what they testified to be more computers than they had ever seen in any one location in their lives. He also had a room that we later learned was dubbed the War Room, which was filled with computers, a long row of computers lined up running. During the course of the search, they asked, "Is there anything on the premises that could endanger us or hurt us? Pellicano said, "No." The agents came across the safe. They had Pellicano open the safe. Inside that safe they found two functional hand grenades, a large quantity of plastic explosives, I believe an expert testified that it was enough plastic explosive to take down an airplane.

Anthony Pellicano: I had them in my evidence safe and completely forgot about it.

Liz Day: Why?

Anthony Pellicano: Well, if you were living my life at the time, I was very chaotic. The FBI will tell you that I was just as shocked as they were when they pulled it out of my evidence safe, and I opened up the safe. There's a C4 and grenades, so anyway.

Liz Day: That was something you were holding on to for a client.

Anthony Pellicano: I took away from the client. Yes.

Tiffany Hanssen: Well, if you believe him, first of all, but also, the music is fantastic. Love that music. It really adds something. Really, that illustrates the lengths that he is willing to go to, yes?

Liz Day: Yes, that's why he was so successful because Pellicano was the guy you called, who would do anything in order to solve your problem by any means necessary. What we show in the documentary is that meant that a lot of innocent people got hurt. I think we explored the question of, what accountability should the lawyers who hired him over and over and the big-time celebrities who benefited from his work suffer for the crimes that he did on their behalf.

Tiffany Hanssen: We know he went to jail, was he remorseful, resentful of his time in prison, how would you characterize that?

Liz Day: I think Pellicano is very proud of the fact that he served his time and did not rat, in his words. He makes the point of saying, "I could have gotten a lesser sentence if I would have ratted on my clients." He also, again, is a good example of wanting it both ways. He would claim, "None of the lawyers or clients knew for a fact, I didn't tell them that I was wiretapping and breaking the law," Then he also would say that he could have ratted on people and gotten a lesser sentence so we were never really able to get him to square how those two things could be true at the same time. He was proud of the fact that he served his time, and he never ratted because, ultimately, loyalty to him is what defines his moral code.

Tiffany Hanssen: The other thing I think that he likes to see maybe, and I'm totally speculating, as buffeting his moral standing is, he'll say, "I never went after anybody innocent. I never heard anybody innocent," which of course, just screams rationalization. I just wanted your take on that.

Liz Day: Yes, that was really interesting. Pellicano told us he had no remorse for what he did. He doesn't believe that he really hurt anyone. He thinks that he never went after any innocent people. He thinks that anyone he was up against deserved it. Over and over again in the documentary, we interview these victims who described what they experienced and how they were hurt by him. Then we present that question to Pellicano. He will again and again just deny. "Oh, I never did that. Oh, they're making that up." We say, "Pellicano, you were convicted of these crimes. There was other evidence that you did these things." He still maintained that he never did any of those things.

Tiffany Hanssen: Before I let you go, will there always be people like Pellicano?

Liz Day: Yes. We have a line in the documentary that the government went after the supply but not the demand. There's always a hunger for someone who is willing to break the rules and for powerful people. If it's not Anthony Pellicano, it's somebody else.

Tiffany Hanssen: A new two-part documentary from The New York Times sheds light on Anthony Pellicano. It's called Sin Eater, and it's airing on Hulu FX. Reporter, Liz Day, who led the team about the Britney Spears conservatorship case, also worked on this series. Liz, thanks so much for your time today.

Liz Day: Thank you.

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