Apple Chief Executive Officer Tim Cook made $41.5 million after taxes in his biggest share sale in two years, a U.S. securities filing showed.
Cook sold 511,000 shares, which were worth about $87.8 million before accounting for taxes, according to the filing dated Tuesday. He made $355 million from a stock sale in August 2021.
The Apple chief owns about 3.3 million shares, valued at about $565 million, following the sale, the filing showed.
The company's shares have fallen 13% from their record high of $198.23 in July as investors fret about a slower-than-expected recovery in smartphone demand.
Apple launched its new iPhone 15 lineup last month, without raising prices, a move that some industry watchers said was in response to a global smartphone slump.
Shares of the Cupertino, California-based company were down 0.6% in trading before the bell.
Analysts at KeyBanc downgraded the stock to "sector-weight" from "overweight" on Wednesday on worries that sales growth in the United States - Apple's largest geographical segment - was likely to slow again in the fourth quarter.
The brokerage noted that fewer phone users in the United States were likely to upgrade their devices as they grappled with high inflation.
A report from research firm Canalys showed North American smartphone shipments were expected to fall 12% in 2023.