Insider Investment: A Bullish Signal from a Proven Executive

One strong recent example is Mark T. Bertolini (former Aetna CEO, now Chairman/CEO of Oscar Health - ticker: OSCR).

On April 6, 2026, he purchased 1,000,000 shares of Oscar Health in a private placement at $11.92 per share (total ~$11.92 million). This is a very recent open-market-style insider buy within the last month.

Why it fits your criteria (previously made money on stock purchases): Bertolini has a proven track record of profiting from company stock. As CEO of Aetna (2007–2018), he oversaw massive value creation—the stock delivered enormous total shareholder returns (roughly 480–650%+ under his leadership, depending on the exact timeframe). Aetna was acquired by CVS Health in 2018 at a huge premium (~$207/share), and reports at the time valued Bertolini’s personal holdings and compensation in the company at over $420 million. He directly benefited from Aetna stock appreciation and the deal, making him a clear example of an insider who has previously cashed in profitably on his company’s stock performance.

This is a classic case of a high-profile executive with skin in the game putting fresh capital into his current company after a history of successful (and lucrative) involvement with public company stock. Insider buys like this are often watched as a bullish signal, though of course past performance doesn’t guarantee future results—always do your own due diligence.