By 2001, His Amazon Shares Had Fallen 93% And Wall Street Was Predicting The Company Would Go Bankrupt. Bill Miller Didn’t Care, He Doubled Down At $6 A Share. Two Decades Later He Had More Amazon Stock Than Anyone Not Named Bezos
While Wall Street analysts declared Amazon headed for bankruptcy and the stock cratered over 90%, one fund manager read a single line in the financials that changed his mind and kept buying. His conviction cost him almost everything before it…
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Amazon’s Darkest Year Started With a Cash Warning
On June 23, 2000, Lehman Brothers analyst Ravi Suria published a report warning Amazon (NASDAQ:AMZN | AMZN Price Prediction) would run out of cash within four quarters unless it raised more debt. The shares fell 19.4% that day to $33.825, and Suria kept issuing negative reports for eight months after.
The slide kept going. Per CNBC, the stock bottomed around $6 in 2001. Bankruptcy talk moved from the fringe to the consensus.
What One Manager Found in the Cash Flow Statement
Bill Miller, who ran Legg Mason Value Trust, saw something else. Per The Investor’s Podcast, Miller bought Amazon at its IPO, doubled his money, sold, then re-entered at $88 a share in the late 1990s. The fall to roughly $6 was about a 93% decline from his re-entry price.
Miller’s reasoning was mechanical: Amazon’s book business generated positive free cash flow with minimal inventory risk since customers could return books for refunds. A retailer with those traits is hard to push into insolvency, so Miller concluded the bankruptcy call was wrong and bought more as the stock fell.
The market was reading the share price and inferring it. Miller was reading the cash flow statement, which showed a core business funding itself. That gap between price and cash generation is the entire lesson, and it is the same pattern behind the recent runners we studied in a free guide to the winners most investors walked past.
Inside Miller’s Meetings With Bezos
Miller asked Jeff Bezos what took his time. Bezos answered: “The balance sheet. I’m making sure that the balance sheet is as bulletproof as I can make it.” By 2002, Bezos changed to discussing customer experience, which Miller read as Amazon moving from defense to offense.
Miller also remembered offering Bezos between $100 million and $200 million in financing if needed. Bezos declined.
A Payoff Few Investors Stayed Around to Collect
Amazon has returned 82,169.55% from October 1, 2001 through this morning, with shares at $247.22 as of 9:47 a.m. ET on September 30, 2026. That return is split-adjusted, which is why it does not line up exactly with a move from $6 to today’s quoted price.
By 2020, Amazon made up roughly 83% of Miller’s personal portfolio, and he was known as the largest individual Amazon shareholder outside the Bezos family as of that year.
Miller beat the S&P 500 for fifteen consecutive years, from 1991 to 2005. Disciplined security selection produced the position.
His net worth has been estimated at around $500 million, a dated figure. Separately, in April 2021 he claimed billionaire status, which he attributed to Bitcoin (CRYPTO:BTC) gains rather than Amazon.
MarketWatch reported on January 4, 2022 that Miller laid out succession plans, and The Business Journals reported the same day that he would hand off management of his funds. A Miller Deep Value Strategy first-quarter letter published April 14, 2026 shows the firm continues.
Why This Lesson Lands in a Soft Week
Amazon is down 7.21% over the past month and 3.04% over the past week. Holding through a 93% drawdown is nearly impossible in real time, which is why few investors did it. The takeaway: when price and cash flow tell different stories, check which one the market is actually reading.
Contact [email protected] for any questions or corrections.
AJ spent 10 years writing about financial markets at The Motley Fool. His coverage centers on technology stocks and the broader macroeconomic trends, from interest rates to geopolitics, that shape where markets are headed next. AJ is drawn to the stories where big-picture economics and individual companies collide.
