Oracle Stock: Larry Ellison's 'Buy, Borrow, Die' Strategy

A tax planning strategy known as 'buy, borrow, die' is enabling billionaire Larry Ellison to access liquidity from his substantial Oracle (ORCL) stock holdings without triggering immediate federal capital gains taxes. This method allows investors to borrow against their appreciated assets, with loan proceeds not classified as taxable income. Upon death, heirs inherit the assets at a stepped-up basis, potentially eliminating the capital gains tax liability entirely.

Oracle's stock closed at $146.35 on September 2, 2026, after appreciating 297.66% over the preceding ten years. Ellison's cost basis on his Oracle shares is effectively zero, meaning a sale of $1 billion would incur a significant federal capital gains tax bill, estimated at 20% plus a 3.8% Net Investment Income Tax. By borrowing against these shares instead, he avoids this immediate tax consequence.

The strategy is particularly relevant as Oracle's stock has experienced volatility, dropping 36.79% over the past year, which could lead to margin calls that might force a sale and trigger the taxable event this strategy is designed to prevent.

Estates are subject to estate taxes, with a basic exclusion amount of $15,000,000 for 2026, and a 40% rate on amounts exceeding this threshold. However, for ultra-high-net-worth individuals like Ellison, the 'buy, borrow, die' strategy focuses on deferring income tax liabilities on asset appreciation.