His second, to Wheeler, was a blip in the late ’70s. In the divorce, Wheeler sold her stake in the company that would become Oracle to Ellison for $500—holdings that today would be worth billions.
Next came Boothe. Despite the messiness, they remain friends and she told a biographer that she never wanted to marry again—or even date seriously—after Ellison. Anyone else would be unexciting.
In 2003, he married Craft, a romance novelist, after dating for eight years. Jobs was the wedding photographer. While they were together, Craft published a novel, Man Trouble, about a history professor turned romance novelist who falls for a billionaire tycoon. She said it was only partially based on Ellison. Then came Nikita Kahn, a Ukrainian model. They divorced in 2020.
Between all of that—and sometimes during—were the girlfriends. During an Oprah appearance Ellison said that he hadn’t found the right woman yet, which, after the episode aired, set off a flurry of applicants vying for the job. His Dionysian image is complicated, though; Ellison has been a teetotaler for years and swore off alcohol in his 20s after he drunkenly hit on a friend’s fiancée, he told a biographer.
His habit of dating Oracle employees was well-known inside the company. In the ’90s, a relationship with an administrative assistant, Adelyn Lee, ended badly and she sued for sexual harassment and wrongful termination. Oracle reportedly settled for $100,000, though she was later convicted for forging documents in the suit. Handling the money around all the dalliances fell to the family office. Philip Simon sighed to a colleague once that this was his least favorite part of the job at Cephalopod Corp.
These days Ellison spends his time at his Florida compound or in Oxford, England, where he and Zhu are raising their five young children. How Ellison met his sixth wife is a mystery to people who know him. One version he has told is they met on a trip to Japan, where she’d gone to boarding school. Another version was they met while he was touring the University of Michigan, where she was a graduate student. One friend’s understanding is they met online.
