Anthropic Owes Amazon $110 Billion in Cloud Deal, Draft IPO Filing Shows

Larry Ellison's dual role as backer of Paramount Skydance Corp. and controlling shareholder of Oracle Corp. is stirring concern on Wall Street as both companies pile on debt. Paramount took on $52 billion of additional debt this week to help pay for its acquisition of Warner Bros. Discovery Inc., while Oracle has nearly doubled its long-term debt to more than $160 billion over the past two years as it builds out AI computing capacity, making it the fifth-largest borrower in the US corporate bond market. The cost to insure the debt of both companies against default has converged and is increasingly moving in lock-step, a sign investors are beginning to treat the two credits as intertwined. Ellison, 82, is backstopping Paramount's takeover of Warner Bros., spearheaded by his son David, via a family trust that guaranteed a significant portion of the roughly $47 billion of equity financing for the deal, and the family pledged to take all necessary steps to bring leverage down in the coming years. His fortune has plummeted by almost $200 billion over the past year, though he is still worth roughly $192 billion, and he recently canceled a plan to sell billions of dollars worth of Oracle stock and disclosed he had increased the number of shares pledged as collateral for personal loans. S&P cut Oracle to BBB- in July and lowered Paramount's issuer credit rating to BB last month, and Oracle shares have fallen more than 50% over the past year.

Microsoft generated $182.94 billion of fiscal 2026 operating cash flow and paid $115.95 billion for property and equipment, leaving $66.99 billion of simple free cash flow that covered its $26.45 billion annual dividend about 2.5 times. After dividends, roughly $40.54 billion remained before repurchases and other claims, and $22.27 billion of buybacks used part of that balance. In the fiscal fourth quarter, management reported $41 billion of capital expenditure including finance leases, compared with $35.8 billion of cash equipment spending, with the separately reported $5.6 billion finance-lease component creating future obligations rather than immediate cash outlays. Holding operating cash flow at $182.94 billion, an additional $20 billion of cash equipment spending would cut simple free cash flow to $46.99 billion and still leave roughly 1.8 times dividend coverage, while an additional $40 billion would leave $26.99 billion, close to the dividend bill before buybacks. At September 30's approximate $3.81 trillion market capitalization, the payout was less than 1% of equity value, and fiscal 2026 simple free cash flow implies approximately 57 times free cash flow. Insider Monkey's hedge fund database showed 273 Microsoft holders in Q2 2026, compared with 282 in Q1, with Fisher Asset Management increasing its share position 3% to 26,611,728.