Wall Street's well-known commentator, Jim Cramer, issued a stark caution on Monday regarding the latest reported massive financing arrangement between NVIDIA and OpenAI, stating its structure mirrors the hazardous patterns of the telecom sector just before the 2000 dot-com bubble burst.

"I lived through the year 2000," the "Mad Money" host remarked, "and I don't want to see the sequel."

Cramer's warning comes amid reports that NVIDIA is in discussions to provide approximately $250 billion in financing guarantees for OpenAI. This backing is intended to support the construction of a 10-gigawatt AI data center campus in Ohio. The guarantee would cover the project's leasing and construction debt but does not include the NVIDIA chips installed inside the facility.

Following the news, NVIDIA's stock price fell over 4% on Monday, dragging down several other semiconductor stocks.

Cramer highlighted that the practice of a supplier financing large-scale purchases for its own customers is highly reminiscent of the behavior of telecom equipment manufacturers in the late 1990s. Back then, these companies lent money to clients to boost sales, but when cash-strapped buyers couldn't pay, both the suppliers and investors suffered massive losses.

"The lesson we learned in 2000 was that you shouldn't be lending money to the companies buying your products," Cramer said. He emphasized that he is not bearish on NVIDIA itself, nor is he predicting an imminent collapse of the AI bubble. The real risk, he explained, lies in a chain reaction when a supplier becomes overly dependent on massive spending from a client that is, in turn, heavily reliant on continuous external financing.

He specifically pointed to OpenAI's ability to continue paying for chips through an IPO or other channels as a critical variable. "If the buyer can afford to pay, NVIDIA is in a fantastic position; if it can't, that's a different story altogether," Cramer warned.

Cramer cautioned that the risk is no longer confined to NVIDIA alone. He noted that far too many companies currently have earnings expectations tied to the ongoing expansion of data center investment. "If the market decides to stop funding data centers, and the companies themselves don't have the money, then we'll be right back in the year 2000."