Warren Buffett, one of the world's most successful investors, has built his reputation on identifying valuable businesses and holding them for the long term. But even the legendary investor has made costly mistakes, and one of his most painful acquisitions involved an American footwear manufacturer called Dexter Shoe Company.
In 1993, Buffett's Berkshire Hathaway acquired Dexter Shoe for $433 million, or roughly Rs 4,132 crore at the current exchange rate. The business appeared attractive, with a strong operating record and an established position in the American footwear market.
However, the acquisition eventually became a cautionary tale about competitive advantages, acquisition pricing and the hidden cost of using shares to buy another business.
The most striking part of the story is what Berkshire gave up to complete the deal. Instead of paying cash, Buffett used 25,203 Berkshire Hathaway Class A shares. At the company's latest available closing price of $8,13,595 on October 23, 2026, those shares would be worth approximately $20.51 billion, or around Rs 1.96 lakh crore.
That is a hypothetical present-day value of the shares surrendered in the transaction, not a cash loss that Berkshire Hathaway actually incurred. Nevertheless, the comparison shows why Buffett came to regard Dexter as one of the most expensive mistakes of his investing career.