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And who's bright idea was it to send anything related to this on a work email. You'd think someone in this space would understand encrypted communication.

well the easiest way to not get caught is to not commit crimes. In general, criminals aren't especially smart. Or the ones that get caught at least.

"Criminals aren't smart" is the textbook example of anti-survivorship bias.

Dumb criminals are dumb, and get caught more readily.

Smart criminals have sophisticated networks, trust funds, art deals and charities to obscure their activities, and do not get caught as frequently.

for ref: Mossack Fonseca.

Fucking Epstein had his own Internet network

that is really covering your ass

Seriously, you’d think that an IT guy at a security company would know better than that.

Seriously, it would be smarter to a) use encrypted comm channels and b) use phrases like the weather, or the hockey game. Positive / sunny weather = invest, bad weather = pull out / diversify. Same with sports games. "Oh hey the Wings went 3-0 last week, how you feeling about next week's match?"