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Interesting discussion. In the interview, MacAskill mentioned Madoff as an example of the idea that it’s not about "bad apples." [1] Giving Madoff as an example in this context doesn’t make sense to me. But maybe MacAskill was meaning to say that it's not about "bad apples that are identified as such before/at the time of their fraud"? That would be the only interpretation that makes sense to me, because Madoff sounds like he really was a "bad apple" based on the info in Why They Do It.

Here's what Soltes says about Madoff in Why They Do It (quoted from the audiobook, with emphasis added):

[Madoff] cavalierly remarked, "The reality of it is my son couldn't stand up amongst the pressure anyhow, so he took his own life." In the many hours of conversations I had with Madoff, this statement stood out for its callousness. A father [who] couldn't understand the impact that his actions had on his own son...

...Madoff remains dispassionate even about the circumstances that are of the greatest significance. In September 2014, a colleague emailed me news that Madoff's second son, Andrew, had just died of cancer. As I was beginning to read the article, my office phone rang. I picked it up and was surprised to hear Madoff on the line. 

He had heard the news of his second son's death on the radio, and asked if I could read the obituary to him. Shaken by the fact that a father had called me to convey news of his son's death, I turned my attention to describing the news in the most compassionate way I could. I wasn't a professor or a researcher at that moment, just one person speaking to another. 

I read him a writer's article about his son's death. When I reached the end, I was at a loss to know what to say. Instinctively, as we often do when hearing of a death, I asked him how he was doing. 

Madoff responded, "I'm fine, I'm fine." After a brief pause, he said that he had a question for me. I thought he might want me to send a copy of the obituary to him or deliver a message on his behalf to someone. It wasn't that. Instead, he asked me whether I'd had a chance to look at the LIBOR rates we discussed in our prior conversation. 

This particular phone call with Madoff stuck with me more than any other. Shortly after finding out his son had died, Madoff wanted to discuss interest rates. He didn't lose a beat in the ensuing conversation, continuing to carry on an entirely fluid discussion on the arcane determinants of yields. It didn't seem as though he wanted to switch topics because he was struggling to compose himself, and it didn't seem as though he was avoiding expressing emotion because the news was so overwhelming. In some way, it almost seemed as though I was more personally moved by the death of Andrew in those moments than his father.

To a psychiatrist, Madoff displays many symptoms associated with psychopathy...while labels themselves are of little use, viewing Madoff through this lens helps place his prior actions and current rationalization of that behavior into context. 

Madoff interprets and responds to emotion differently from most people. Regardless of how close he got to his investors, his personal limitations enabled him to continue his fraud without remorse or guilt…Madoff has an inability to empathize with his investors…he never experienced the gut feeling that he needed to stop…he managed to create extraordinary suffering for his investors, his friends, even his family, while experiencing little emotional turmoil himself.

  1. ^

    Here’s a quote from MacAskill (emphasis added): 

    So the lesson that Eugene Soltes takes in his study of white collar crime that actually like the normal case of fraud like typical cases of fraud comes from people who are very successful, actually very well admired, really not the sort of people where it's like, Oh yeah, they were, everyone was talking all along about how this person's, you know, bad apple or not up to no good. Instead, you know Bernie Madoff even was the chair of NASDAQ...And so you know what he really emphasizes instead is importance of kind of good feedback mechanisms, again, because, you know, people are not often making this these decisions in this careful calculated way. Instead, is this like mindless, incredibly irrational decision...