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Of course. He would do it again if he could. We are talking Bernie Madoff.
He was a serial killer in a suit.
That's very possible.
But I don't think that's the case for the vast majority of people who end up in jail for a significant amount of time for something they did after already becoming wealthy. I'm sure if offered the chance, most of them would go back in time to the point where it turned from slap-on-the-wrist white collar crime to your-get-out-of-jail-card-ain't-working-here stuff. Basically deciding to stick with the $500k tax evasion that gets them probation if caught instead of the $5m that gets them behind bars.
FWIW, I'm assuming that Bernie Madoff already was regular yacht-rich before starting that Ponzi scheme to become super-yacht-rich. Based on the things I've read, some people disagree on that and think the jail worthy behavior started even before that.