SEATTLE -- Jeff Bezos filed plans Monday to sell nearly $4.1 billion in Amazon stock as shares hit a new all-time high.

Since stepping down as Amazon’s CEO in 2021, the company’s founder has been selling off tens of billions of dollars’ worth of Amazon stock. The sales are part of prearranged trading plans, which are meant to shield corporate executives from insider trader allegations.

On Monday, Bezos, who remains Amazon’s executive chair, filed SEC documents showing he planned to sell 15 million Amazon shares, worth $4.07 billion. The decision was made the same day Amazon’s stock crossed the $3 trillion market capitalization threshold for the first time.

The Seattle-based e-commerce giant blew past quarterly earnings estimates last week with a 20% revenue increase from a year ago, driven by better-than-expected cloud-computing growth. The surge signaled to investors that the company’s massive artificial intelligence investments are paying off.

Over the two market days after the July 30 earnings call, Amazon’s stock spiked around 20%, reaching an all-time high Monday.

As a result of the timing, Bezos is walking away with a yacht-load of cash from the chunk of shares he acquired in 1994, when he founded the company. But the sell-off isn’t a strategic move Bezos made after the earnings call, considering the sale was preplanned in November.

The details of prearranged trading plans aren’t usually public, so it’s difficult to know why the proposed sale was filed that exact day. Although trading plans sometimes lay out specific dates or holding durations, they also can trigger actions when a stock hits a specific market value.

Still, it appeared the rest of the market felt bearish after news broke of Bezos’ plans. Amazon’s stock dropped around 2% Tuesday morning.

The sell-off only represents a small portion of Bezos’ Amazon stock, which totaled 950 million shares as of February, according to Amazon’s 2026 proxy statement. Bezos remains the company’s largest individual shareholder, with 8.8% of the company.

The last time Bezos filed plans to sell shares was June 2025, when he planned to sell 25 million Amazon shares by May 2026. Those shares were worth around $4.75 billion at the time.

Bezos’ sales come after he ditched his longtime Seattle-area residence for Miami three years ago. The relocation to Florida, which has no capital gains tax, has allowed the multibillionaire to save big on taxes when selling off his stock.

Two months before Bezos stepped down as CEO in 2021, the Washington Legislature adopted a 7% excise tax on individual net long-term capital gains exceeding a standard $250,000 threshold. Last year, lawmakers added a 2.9% surcharge on long-term gains exceeding $1 million, raising the top rate to 9.9%.

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