“A crash is coming…I just can’t tell you when, and I can’t tell you how deep,” Says Renowned Financial Journalist, Andrew Ross Sorkin

After spending almost a decade studying the 1929 crash, Sorkin has a warning: it’s happening again. Now, the bestselling author of Too Big to Fail, an account of the government interventions needed to get the economy back on its feet after the Great Financial Crisis, says Wall Street today mirrors the reckless speculation and borrowed money that fueled the market bubble before the Great Depression.

But this time, he warns it’s AI hype instead of margin trading—and the guardrails designed to protect you are being dismantled. “A crash is coming…I just can’t tell you when, and I can’t tell you how deep.”

The Warning

In his new book, 1929: Inside the Greatest Crash in Wall Street History, Sorkin says the Roaring Twenties have a warning for those watching the market today.

The problem, for Sorkin, isn’t simply that the stock market is at record highs—it’s that it’s happening despite a fundamentally worsening economy and geopolitical uncertainty. This means the market is providing a heady mix of rampant speculation, excessive debt, and what Sorkin calls the “guardrails coming off” that would normally protect investors.

“I’m anxious that we are at prices that may not feel sustainable,” he says, citing the massive investments in AI in particular.

Lessons from 1929 

Easy credit was the explosive force that fueled the stock market bubble in the 1920s.

Before the early 1900s, Americans rarely went into debt, largely because of religious and moral stigmas. Then General Motors popularized consumer credit to buy cars, igniting a revolution in American consumer culture. Soon, Wall Street saw an opportunity. The same principle could work for stocks: If a person could buy a new car on a credit plan, the argument went, why not a diversified portfolio of stocks, with just 10% down and 90% on margin (borrowed money)?

In good times, “it felt like free money,” Sorkin says. It’s the same argument often made today—allowing ordinary investors to bet with their retirement money on high-flying private equity funds and cryptocurrencies, but with far fewer investor protections and disclosures than public stocks.

Ordinary investors a century ago bought stocks on margin, only to be wiped out when the market crashed in 1929. Today feels eerily similar, only now with meme stocks, record numbers of exchange-traded funds with PhD levels of financial engineering often aimed at retail investors, and alternative investments like crypto.

Today’s Market Mood

Sorkin suggests that the current market exhibits several hallmarks of speculative mania. AI stocks have soared as investors clamor to bet on the next big tech innovation. Hundreds of billions of dollars have been thrown into the space, inflating valuations to stratospheric heights, even as broader concerns over economic slowdowns and geopolitical risks loom. 

At the same time, ordinary investors are often told they should be taking risks on private investments in their 401(k) retirement accounts—another parallel to the past, only with fewer safeguards or disclosures about risks (the pitch from politicians has been about “democratizing” access to building wealth).

Debt is high. Speculation is rampant. And what investors think is beginning to sound “too good to be true” is starting to look a lot like other bubbles Sorkin has covered during his career, from 1929 to 2000 to 2008 to today.

Expert Context 

Not everyone shares Sorkin’s pessimism. BlackRock’s (BLK) Larry Fink, CEO of the world’s largest asset manager, argues that opening up retirement funds to private equity and other riskier investments offers ordinary investors a chance to gain much better returns. And Fink, who once dismissed bitcoin as a tool for money launderers, now sees crypto as a smart component in most portfolios, similar to gold.

He’s not alone in suggesting that parallels to 1929 may be overblown. Today, there are stronger banking regulations, Federal Reserve interventions, and sophisticated risk management tools. However, these arguments often gloss over the same dynamic Sorkin frets about—not that we’re teetering on the edge of a cliff, but that the protections specifically put in place to prevent Wall Street excess are being removed at just the time they might be most needed.

The Bottom Line 

Sorkin sees uncomfortable parallels between today’s market and the pre-crash market of the late 1920s: soaring valuations driven by technological hype, increasing debt levels, speculative fervor in assets like memecoins, and a systematic weakening of investor protections—all wrapped in the appealing rhetoric of democratizing finance. While the timing and severity of any future crash remain unknowable, the warning is clear: though history may not repeat, it often rhymes—and investors might just be feeling that beat getting louder.

“I can assure you, unfortunately, I wish I weren’t saying this,” Sorkin says. “We will have a crash.”