Larry Ellison, founder of Oracle, personally guaranteed $40.4 billion of the equity financing for Paramount Skydance's roughly $110 billion offer for Warner Bros. Discovery. This extraordinary show of confidence in his son's media ambitions now faces significant risk. If the deal collapses, Ellison stands to lose an estimated $9.8 billion.

The proposed merger has met fierce resistance, with a coalition of 12 state attorneys general suing to block the acquisition. They argue that combining two of Hollywood's top five studios would stifle competition in theatrical distribution and cable licensing, potentially leading to higher prices and fewer film choices for consumers. This legal challenge represents the sharpest opposition yet to one of the largest media mergers in history.

The timing of these events is unfavorable for Ellison's personal finances. Oracle stock has plunged by approximately 34% in 2026 and nearly 50% since early June. This decline has wiped out an estimated $213 billion from Ellison's net worth, reducing it from a peak of $388 billion to around $175 billion and moving him from the world's second-richest person to roughly eighth. The stock's tumble has quietly weakened the backstop holding up the entire deal, as Ellison's guarantee relies on his Oracle wealth. The sell-off is primarily attributed to increasing market doubts about the return on Oracle's substantial investments in AI and cloud infrastructure.