I don't know, how big is Wall Street nowadays? /s

More seriously: it's likely that there are indeed a lot of "optimally greedy" criminals - it's just that we don't label them criminals, because they don't get caught. I guess the actual numbers are somewhat dependent on your trust in the ability of law enforcement.

> perhaps the consistency of his behavior made it seem 'normal' to the local bankers?

Perhaps it was just the '80s, when banks didn't really want to ask any questions.

> the relationship between intake and risk is probably not linear.

I agree there. Note that criminals do tend to understand this, typically regarding the results of conviction. It's the reason capital punishment is not really a deterrent: because once you pass the threshold (which is often with a single act), punishment does not grow prportionally, so they might as well do it over and over.

Bernie Madoff might be close to an example; his scheme kept going for an _amazingly_ long time, and he made some effort at times to reduce inflow to keep it somewhat under control. There was probably a world in which it only came out after he died; as it was he was kind of unlucky with the timing.

Of course, there might be plenty of optimally greedy criminals out there, and you’ll never know; more or less by definition they do not get caught.

This is the idiocy of committing various forms of graft or embezzlement in the Western world: the rewards are small and short-term compared to the nonzero legal and financial consequences of getting caught. It's that most people are bad at quantifying the probabilities and qualitatively assessing their risk exposure before they're caught and rationalizing they're different and somehow smarter than everyone else at all times. His theft didn't go unnoticed and they eventually had to hire a private detective

Even if someone could steal much quickly the equivalent of, say, a billion dollars without raising any suspicion or leaving any trace evidence and launder it covertly, the problem becomes there is no country to disappear to where the proceeds could be utilized and where property rights are respected: countries including Iceland, Switzerland, Ecuador, Cuba, Venezuela, Russia, Belarus, Afghanistan, Iraq, Iran, Qatar, Yemen, China, and DPRK will not help you. One could attempt to live openly, but they would find it difficult to launder their funds from nowhere into the legitimate banking world without inevitably raising suspicions or being caught through forensic accounting.

Therefore, a wise criminal™ is generally better off using legitimized means to facilitate large-scale wealth transfer from people and organizations that lack economic and political power using trickery, obfuscation, and complexity. Either that, or by creating genuine (or genuine-appearing) value and monetizing it well through work that doesn't involve criminality reduces the risk of ending up poor and/or in prison. Apart from specialized IP or knowledge work ability that can be productized as a startup, the areas of real estate, public markets, and fintech are the most obvious targets for non-lifestyle business models. Other non-/semi-lifestyle business models readily achievable by an individual is becoming a B2B supplier of high-value, high-margin specialized goods that present one or more barriers to entry, i.e., aircraft parts, nuclear energy parts, safety systems, or medical devices.

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