When Michael Burry talks, people listen. After all, this is the guy who saw the 2008 financial crisis coming when everyone else was partying. Now he's got his eye on Alphabet Inc. (GOOGL), and he's not thrilled about what he sees.

A Bond Sale With Ominous Echoes

Burry took to X on Monday to sound the alarm about Alphabet's plan to issue 100-year bonds. "Alphabet looking to issue a 100-year bond," he wrote. "Last time this happened was Motorola in 1997, which was the last year Motorola was considered a big deal."

That's not exactly subtle. Burry's drawing a direct line between Google's parent company today and Motorola Solutions Inc. (MSI) at what turned out to be the peak of its dominance. And the implication is clear: maybe issuing century bonds is what companies do right before everything goes sideways.

The Motorola comparison is particularly striking when you look at the numbers. At the start of 1997, Motorola was among the top 25 companies in America by both market cap and revenue. Its brand was the most valuable in the entire United States, worth more than even Microsoft Corp (MSFT). That's hard to imagine now.

What happened next? In 1998, Nokia Oyj (NOK) overtook Motorola in the cell phone market. Then Apple Inc. (AAPL) launched the iPhone, and Motorola basically vanished from consumer consciousness. Today, Motorola ranks as the 232nd largest company by market cap with just $11 billion in sales. From the penthouse to the basement in about two decades.

What Alphabet Is Actually Doing

So what's Alphabet up to? Multiple outlets have reported that the company is moving forward with a massive bond sale that includes 100-year debt. The Google parent plans to offer debt in dollars, British pounds, and Swiss francs with various maturities.

According to The Wall Street Journal, citing an investor familiar with the matter, the sale will include sterling debt with maturities ranging from three to 100 years, and Swiss franc debt with maturities from three to 25 years. That's a lot of debt, and that 100-year maturity is the real attention-getter.

Alphabet didn't immediately respond to requests for comment, so we don't know their thinking on the Motorola comparison.

Part of a Bigger Skepticism

This warning isn't coming out of nowhere. Burry has been increasingly vocal about his concerns regarding tech giants and their AI strategies. In January, he criticized companies like Microsoft and Alphabet for what he sees as excessive AI infrastructure spending that will quickly become obsolete.

He's also recently bet against Nvidia Corp. (NVDA), questioning whether the AI chip boom is sustainable or just another tech bubble waiting to pop.

Whether Burry's right about Alphabet following Motorola's trajectory remains to be seen. But when the guy who called the housing crisis starts making historical comparisons, it's probably worth paying attention.

Price Action: Alphabet shares were up 0.81% at $325.71 at the time of publication on Monday, according to market data.