On Wednesday, as shares of used car retailer Carvana (CVNA.US) soared, the company's CEO Ernest Garcia III filed documents to sell $192 million worth of shares, marking his largest personal reduction in holdings since the company went public in 2017.

According to the Form 144 filing disclosed after the market closed, Garcia plans to sell 630,000 shares through a 10b5-1 trading plan established in December last year. The shares, held by two trusts he controls, represent about 2% of the billionaire's stake in Carvana. It is important to note that Form 144 only discloses a planned sale, not a completed transaction.

Garcia, who has a net worth of $9.7 billion, according to the Bloomberg Billionaires Index, has never previously sold more than $2.1 million in a single transaction, Form 4 filings show.

Carvana shares surged to $305.52 at close on Wednesday, up nearly 18% since the company reported strong sales and earnings numbers in May.

It was also disclosed that Garcia's father, Ernie Garcia II, announced on Tuesday through a 13D/A filing that he had sold call options on 4 million Carvana shares (approximately 9% of his holdings) to Citi. The options give Citi the right to exercise them by April 17, 2026 at $400 per share, a 31% premium to Wednesday's closing price.

Such structured call options mean that the seller, Garcia, will benefit if the stock price remains below $400. As terms of the transaction, Garcia II also disclosed the pledge of an additional 9 million Class A and Class B shares as collateral.

Garcia II, who has a net worth of $20.3 billion, according to the Bloomberg Wealth Index, sold more than $1.4 billion of stock last year when the company's stock price was recovering from a crash in late 2021, when its share price plummeted from an all-time high of $361 to less than $5.