Larry Ellisons about-face on an Oracle stock sale sparks chatter in Silicon Valley, Hollywood

Larry Ellison’s disclosure last week that he planned to sell $7.5 billion in Oracle stock got tongues wagging across Silicon Valley and Hollywood – but what really sparked chatter was the quick about-face that came a day later.The 82-year-old software tycoon – who built one of the great American tech giants through decades of legendarily shrewd M&A deals – revealed in a Friday securities filing that he planned to sell 50 million Oracle shares. Ellison adopted the so-called 10b5-1 plan on June 22 and the share sale was slated to be completed by Oct.24, according to the filing.
So it struck many as odd when the very next day – a Saturday, no less – he revealed in a second filing that he had changed his mind, that he hadn’t sold any shares and that he was scrapping the whole idea.And what’s happened since? Oracle this week reportedly started yet another round of layoffs after slashing 13% of its workforce last year as it makes a massive bet on AI infrastructure, according to reports.The stock has continued to bounce downward.Was this Ellison being crazy like a fox? Some folks are reckoning not – and that the disclosures instead look like the fumblings of a player who’s at the close of his career and ready to pack it in. “Larry obviously concluded that selling could be damaging to Oracle supporting his wealth and the company’s,” said one Silicon Valley financial executive who asked not to be quoted by name. “The unexplained Ellison reversal introduced another layer of uncertainty exactly when investors were already questioning Oracle’s business model.”To be clear, I’m not saying I necessarily agree that this is a simple case of a blunder.
Count me among those who are still scratching their heads. A press rep for Oracle had no immediate comment.Ellison, it should be noted, is no longer the CEO of Oracle, but he’s still executive chairman and also its chief technology officer.Meanwhile, Oracle shares are down roughly 53% from...