Since then, Las Vegas Sands shares have skyrocketed to $54, meaning Adelson's initial purchase is now worth north of $600 million.
Though Jamie Dimon's gains are hardly the 1,700 percent rally that Adelson saw, his 62 percent gains are nothing to sniff at. Dimon first bought $11.5 million in JP Morgan stock in early 2009, and added $17.1 million to the pile in July 2012 — when the shares fell on the bank's London Whale trading blunder. Shares are up 40 percent since the most recent purchase, meaning Dimon's bets have made $18 million overall, according to InsiderScore. (Read More: Fed Slaps JPMorgan on Wrist With London Whale Order)
While executives are restricted from selling around material announcements, they do have, to be sure, the best read on company performance, strategy and sentiment. The other group with access to this information: Company boards of directors.
It was on Starbucks' board of directors that Facebook COO Sheryl Sandberg nabbed $126,000 of the coffee company's shares. From her April 2010 open-market purchase — that slice is up 104 percent. Sandberg left the company's board in late 2011, and may have cashed out some of her position (the rules for disclosing insider transactions become less stringent when an executive leaves a company).
Bank directors are seeing their stocks rising, too. CVS Caremark CEO Thomas Ryan bought into Bank of America while sitting on the Charlotte-based lender's board during the financial crisis. Ryan got 50,000 shares of BAC at roughly $5.60 a piece in January and February 2009 — the stock has more than doubled since then. Citigroup director Roberto Hernandez has seen his $7.5 million stake in international lender rise by $18 million, or 240 percent, since he purchased it in March 2009.
Some lesser-known companies have directors whose stakes are in the 400 percent-plus club. Harley Davidson director George Conrades has seen his $500,000 share purchase rise 400 percent. Dana Anderson, vice chairman of the board at Macerich, bought on eight occasions throughout the depths of the crisis. Anderson's move was a prescient one for a director at a real estate developer; while she's sold off a portion of the stake, her 116,000 shares are up more than 400 percent.