Warren Buffett's "most gruesome mistake" was buying Dexter Shoe in 1993, a Maine shoemaker that soon collapsed under pressure from cheap foreign imports.
"I gave away 1.6% of a wonderful business ... to buy a worthless business," Buffett said in his 2007 letter to shareholders. The so-called Oracle of Omaha acquired Dexter for 25,203 Class A shares, worth $433 million at the time. While Buffett was wildly wrong about Dexter's prospects, he did recognize the threat that would soon sink the company: cheap, imported shoes from low-wage countries. However, he joked that "someone forgot to tell" Dexter's managers and workers about that challenge, as their factory was "highly competitive against all comers."
In turn perhaps one of the best business deals ever by the then owners of Dexter Shoes? Theron_Mohamed Do they still own the shares?