Oracle Just Raised Its Dividend for a 12th Straight Year to $2 a Share, Even as AI Spending Pressures Free Cash Flow. Is Larry Ellison's Payout Still Safe?

If you own shares of Oracle (NYSE: ORCL) and watch Chief Technology Officer Larry Ellison collect a $579 million dividend check each quarter, it would be natural for you to wonder if the company can really keep those payouts intact while it's burning through cash to build new AI data centers.

The short answer is that the dividend looks reasonably safe today, but its longer-term viability is now tied directly to how well Oracle's massive AI bet plays out over the next few years.

Larry Ellison, CTO of Oracle. Image source: Oracle Corporation.

Oracle has turned itself into a dividend story. The board has raised the payout for 12 straight years, lifting the annual dividend from $1.70 to $2 a share, and most recently distributed another $0.50 quarterly payment on July 24. For Ellison, that adds up to roughly $2.3 billion a year on a stake of about 1.16 billion shares, which tells you how personally invested he is in keeping the checks coming. For a regular shareholder, the yield is modest at roughly 1.3% to 1.4%, but the payout ratio is in the mid-30% range, and dividend coverage of around 4 times shows the dividend is comfortably supported by accounting earnings.

Oracle is spending a lot of money on AI

The tension comes from the cash side of the story. Oracle is in the middle of one of the most aggressive AI infrastructure build-outs in the tech sector. It spent about $55.7 billion on capital expenditures (capex) in its recently completed fiscal 2026, above its own $50 billion target, and is guiding for roughly $70 billion of net cash outlay in fiscal 2027 plus another $20 billion to $25 billion funded by partners. That spending has already pushed its free cash flow to somewhere around negative $23.7 billion, and management has signaled plans to raise roughly $40 billion to $50 billion by issuing new debt and selling new equity to fund its ongoing build-out. In plain language, Oracle is borrowing heavily to build AI data centers while still sending $2 a share annually to investors.

So is the payout still safe? For now, yes, largely because Oracle's income statement and backlog look strong. Its cloud infrastructure and database revenues are growing quickly, its remaining performance obligations have surged into the hundreds of billions of dollars, and the dividend is small relative to the scale of the business. Meanwhile, Ellison still desires to be compensated in cash for his stake rather than only in paper gains. If you are thinking about the next couple of years, the bigger risks sit with the AI plan itself: execution, customer concentration around OpenAI, and Oracle's ability to manage a much larger debt load.

In that context, the dividend starts to look like a promise Oracle will work hard not to break. Cutting it would send a harsh signal to the market and to Ellison himself. As long as Oracle's AI contracts continue to convert backlog into real cloud revenue and the balance sheet remains manageable, the $2 per share payout should be fine.

Micah Zimmerman has no position in any of the stocks mentioned. The Motley Fool has positions in and recommends Oracle. The Motley Fool has a disclosure policy.