Buffett called a Berkshire stock deal for Dexter Shoe his ‘most gruesome’ mistake, worth a Guinness spot

Warren Buffett, the longtime face of Berkshire Hathaway, has been quoted calling at least one investment his “most gruesome” mistake, saying the episode deserves recognition in the Guinness Book of Records. The deal, as recalled in a recent market-news roundup, involved Berkshire Hathaway paying for Dexter Shoe with Berkshire stock.

According to the recap, Buffett characterized the transaction as a serious failure for Berkshire Hathaway and its shareholders. The criticism was not about a small misstep, but about the economics of exchanging Berkshire shares for an acquisition at a time and price that did not work out for owners.

The story underscores a core tension in Berkshire’s capital-allocation approach: the company frequently discusses the discipline of buying businesses and investments only when the price is right. In this instance, Buffett’s later language suggests that the valuation and the chosen form of payment (Berkshire stock) did not produce the intended outcome for shareholders.

While the market-news piece focuses on Buffett’s retrospective judgment, it also reflects why Berkshire’s history remains a regular subject of debate among investors and business historians. Buffett’s public comments often distinguish between operating mistakes and financial-structure mistakes, and the “financial disaster” framing points to the latter, in this case the decision around what Berkshire was giving up and what it was receiving.

Berkshire Hathaway, listed on the NYSE as BRK.B, is an umbrella company known for buying and holding stakes in operating businesses and public securities. Its long-running track record has elevated Buffett’s words on deal-making and valuation, so when he points to a mistake, markets pay attention to what it might imply about opportunity costs, pricing discipline, and the risks of using the company’s own equity as currency.

The episode also highlights a practical point about stock-based acquisitions. Paying with shares can work well when the acquirer’s stock is undervalued by the market, but it can magnify losses when the stock is priced too high. Buffett’s later description in the recap suggests that, in this case, the deal’s economics were unfavorable for Berkshire’s owners.

Still, important details were not included in the market-news recap. It does not lay out the acquisition timeline, the exact terms of the Dexter Shoe transaction, the size of the consideration, or how the investment performed relative to expectations. Without those specifics, it is not possible to assess whether the “disaster” was driven mainly by operating deterioration at Dexter Shoe, broader market conditions, or the valuation embedded in the stock payment.

For investors watching Berkshire Hathaway’s evolving disclosures and shareholder communications, the main takeaway is less about the particulars of Dexter Shoe and more about what Buffett’s own retrospective critique indicates. The company’s leaders and investors will continue to scrutinize how Berkshire chooses deal structures, especially when it uses its own equity rather than cash, and what lessons Buffett draws from older transactions. “Most gruesome” is strong language, and it suggests the failure was clear to him with time.