You know, insider trading is probably one of the most fascinating violations to study in financial history. It’s a topic that shows how even the biggest names can fall when they give in to temptation. Regulators like the SEC and FINRA relentlessly pursue these cases, but some scandals have still managed to leave an indelible mark on people's minds.

Let's start with Ivan Boesky in 1986. This guy was once a respected arbitrageur on Wall Street, but he amassed over $200 million in illegal profits by using confidential information obtained from investment bankers. His case really exposed the corruption network that had taken root on Wall Street and led to the downfall of financier Michael Milken. Boesky eventually cooperated with federal authorities, served three years in prison, and paid a $100 million fine.

Fast forward to 2009, and we find Raj Rajaratnam with the Galleon Group. This guy orchestrated one of the largest insider trading rings ever uncovered. He had sources everywhere — Intel, IBM, McKinsey & Company — and he and his associates pocketed $70 million illegally. What was particularly interesting is that investigators used wiretaps, a technique rarely seen in white-collar crime investigations at that time. Rajaratnam received an 11-year prison sentence in 2011.

But famous insider trading cases aren’t limited to top-tier financiers. Martha Stewart in 2001 shocked the public. She sold nearly 4,000 shares of ImClone Systems just before the FDA rejected its cancer drug. She wasn’t convicted of insider trading per se, but for obstruction of justice and false statements. Five months in prison. This case showed that insider trading could touch cultural icons, not just Wall Street elites.

The same year, Jeffrey Skilling at Enron played a central role in the fraud. Before the spectacular collapse, he sold about $60 million worth of stock based on confidential information about the upcoming bankruptcy. Convicted in 2006 for fraud and insider trading, he initially received 24 years, which was later reduced to 14 years.

And then there’s the lesser-known story of R. Foster Winans, a Wall Street Journal journalist in 1985. He leaked upcoming stories from his "Heard on the Street" column to brokers who made profitable trades before the information became public. Simple but effective scheme. 18 months in prison for him.

Sam Waksal, the real pivot of the ImClone scandal, tried to sell family shares and warned others before the FDA’s negative decision on Erbitux became public. Seven years in prison for him, which paved the way for Martha Stewart’s subsequent scrutiny.

More recently, Steven A. Cohen and SAC Capital in 2013. Cohen is one of the most successful hedge fund managers in history, but his firm was hit with a $1.8 billion fine for insider trading. Eight employees were convicted. The firm had to shut down its investment management operations. This case shows how deeply insider trading can be rooted in high-end institutional investments.

These major scandals illustrate how insider trading cases continue to shape the financial world. It’s a reminder that no matter your status or wealth, regulators will always catch those who play by their own rules.