Larry Ellison to sell up to $8B worth of Oracle stock

Larry Ellison, the co-founder and chairman of Oracle, is planning to sell up to $7.5 billion worth of his Oracle stock, a move that would roughly double the total amount he’s sold over the past decade and a half in a single transaction. A break from the playbook Ellison currently owns approximately 1.16 billion shares of Oracle, a stake that represents roughly 40-41% of the company. His preferred approach has long been what estate planners call “buy, borrow, die.” The logic is elegant in its tax efficiency: hold appreciating stock, pledge those shares as collateral for personal loans, and never trigger capital gains taxes by actually selling. When the owner eventually passes away, heirs inherit the shares at a stepped-up cost basis, and the tax bill vanishes like it never existed. To put the scale of this planned sale in context, Ellison’s cumulative Oracle stock sales since 2010 have totaled around $7.5 billion. In no single year did he sell more than $1 billion worth. A sale of this magnitude would effectively compress 15 years of selling activity into one concentrated move. The liquidity question One possible explanation lies in Ellison’s increasingly complex web of personal fin...