CNN legal analyst Jeffrey Toobin recalls his friendship with former Stormy Daniels' attorney Michael Avenatti and how he deserved his fall from grace in an interview Friday with Anderson Cooper. <blockquote>ANDERSON COOPER, CNN: It's difficult to imagine a more dramatic fall than this. With me now, CNN's chief legal analyst, Jeffrey Toobin. An old-fashioned shakedown is what they were calling it. JEFFREY TOOBIN, CNN CHIEF LEGAL ANALYST: You know, I -- today, I was thinking of -- I'm sure many people remember, he was on CNN a lot of times. COOPER: I did stories, not just the Stormy Daniels interview, that he was -- that he was part of, I did previous stories with him on "60 Minutes," on other cases. TOOBIN: And I got to know him. And I remember once at the peak of all of this, we went to lunch in Midtown, when our offices were in Midtown, and we walked back together to CNN, and it was like walking with a major, major celebrity. People came up to him, it's like, you know, go for it. Go get Trump. You know, he had this hashtag bossta. People remember that. And at the peak of this, he even announced he was considering running for president and he went to Iowa, he went to New Hampshire. And to call it hubris is not even -- doesn't do it justice. I mean the craziness of this. And when you look at this case and the three cases -- he's 48 years old, he could be looking at decades in prison. COOPER: Really? TOOBIN: Oh yes. COOPER: So there's this case which -- I mean Polo Sandoval said 40 years is possible? TOOBIN: I think that's unlikely, but the way the sentencing guidelines work is that it's based on the amount of money at issue in the case. And he's accused of trying to extort $15 million. So if they use that $15 million as the number in the sentencing guidelines, he could be looking at decade in prison. And the California case is worse. No question. COOPER: One of the cases is -- one of the California cases is the Stormy Daniels case? TOOBIN: No, the -- Stormy Daniels is here in New York. And it involved him taking approximately $300,000 of a book advance that she was supposed to get that instead he just pocketed and spent on his own money. The California case is much worse, because, first of all, it's millions of dollars. And also, he was the lawyer in cases where there were awards to his clients and again, he pocketed the money. People in need, people had, you know, problems, that's why they got this award in the first place, also stealing money from his law partners. Again, millions of dollars is an issue. And all of these sentences are based on the amount of loss. So, I mean, these are big numbers. COOPER: Avenatti's attorney said that they are planning to file a motion to change his conditions of confinement, because they are inhumane. TOOBIN: Well, he's in the MCC, which is where they hold people in federal court before trial. You know, it's a lousy place to be. It's worse than being in prison, because it's a much more confined condition. He had his bail revoked, so he's been locked up during this trial. He's obviously now that he's convicted, he's certainly -- COOPER: He had his bail revoked because he was accused of trying to hide money, correct? TOOBIN: Trying to hide more money involving a divorce that he's going through. I mean, the total collapse of his life is really sort of extraordinary. And frankly, you know, I feel kind of snookered, because I took him seriously. I think we all, you know -- COOPER: Well, I mean he was -- I mean, prior to even this Stormy Daniels story, he had won a large judgment in a class action lawsuit, I think it was, in California. TOOBIN: Yes. COOPER: And I had actually done a "60 Minutes" report about the case that he had and interviewed people. I mean, he won a large jury verdict that then got reduced later on. TOOBIN: Right. And he did -- and, you know, he did represent Stormy Daniels and I think in retrospect her legal strategy was kind of insane. I mean, the fact that, you know, she was suing to be cleared of a nondisclosure agreement that they weren't enforcing at all. I mean, he just -- he wanted to gin up a fight with the President. But he lost every case that he brought on Stormy's behalf. And now he's accused of stealing money from her, as well. But, you know, there was a real pathology at work. COOPER: Right. The accusations would show I mean an extraordinary pattern of abuse. TOOBIN: And it's all involving stealing money. It's all involving taking money that was destined for clients, that was destined for law partners. You know, he had this really extravagant lifestyle. He drove Ferraris and races. I mean he had like a Ferrari and private planes. And I think it's clear at this point he afforded it by taking money he wasn't entitled to.</blockquote>