In 2006, email monitoring was nowhere near what it is today. Filters existed, but they were largely keyword and pattern based, think regex and spam signatures. There was no large scale semantic analysis, no contextual language understanding, and no practical NLP capable of inferring intent. Compute and storage constraints alone made deep inspection of email bodies impractical at scale. Most enforcement relied on metadata headers, IPs, sender reputation, not true content comprehension. Comparing 2006 capabilities to modern transformer based language analysis is simply ahistorical.

But yes Gmail is so much more secure now. You know, Gmail as in Google Mail, the largest marketing firm in existence, capable of serving personalized advertisements simply by scanning the contents of your email.

Your confidence is directly proportional to how incredibly wrong you are.

Back around the 2000s when these executive type people, and rich, or government official did get caught for something, and rare though it was it still happened more often back then, it always seemed to include dumbass emails those people sent. I think the Enron guys were sending emails openly criming and scamming for instance.

It's that they were too arrogant to think anyone would dare to look and do anything about it. They were mostly right then but more right now. Worst case scenario now they have to make an ill founded investment in a company a fixer/lawyer tells them about, that money is lost, and travels through layers of shell companies and llc's, and ends up in accounts controlled by the president, and the relevent prosecutors and cops.

I'm not even joking I guarentee the corruption is that widespread now, it is basically a political machine from the robber baron days.