From Apple to Dexter Shoes: Warren Buffett's top wins and biggest blunders in 60 years of investing

Warren Buffett ’s six-decade reign at Berkshire Hathaway is filled with stories of staggering profits, philosophical pivots, and a few painful lessons. As the 94-year-old “Oracle of Omaha” announces plans to retire as CEO by the end of 2025, the spotlight is once again on the investments that made, and occasionally unmade, his fortune.

The genius moves Buffett’s eye for undervalued companies turned modest bets into generational wealth:

• Apple: Despite avoiding tech for years, Buffett dove into Apple in 2016, calling it a “consumer products company.” A $31 billion investment swelled to over $174 billion at its peak.
  
  
• American Express , Coca-Cola , Bank of America: Buffett snapped up these giants when they were out of favor. Together, they've returned over $100 billion, not including decades of dividends.
  
  
  
• BYD: Acting on Charlie Munger’s advice, Buffett bet $232 million on the Chinese EV maker in 2008. That stake peaked above $9 billion before Buffett began trimming it.
  
  
• See’s Candy: Bought in 1972 for $25 million, See’s helped Buffett embrace quality businesses with enduring moats. It has since delivered billions in profit and shaped his investing ethos.
  
  
• National indemnity: This 1967 purchase helped Berkshire amass “float”, the investable funds from insurance premiums — a crucial source of capital. Today, Berkshire’s insurance float stands at $173 billion.
  
  

The costly stumbles Even Buffett got it wrong, and when he did, he owned it:

• Dexter Shoe: Acquired in 1993 using Berkshire stock. The business collapsed, and Buffett later admitted he gave away 1.6% of Berkshire “for nothing.”
  
  
• Missed tech boom: Amazon, Google, Microsoft — Buffett stayed on the sidelines for years. By his own admission, these missed opportunities may have cost Berkshire billions.
  
  
• Selling banks too soon: In the lead-up to the pandemic, Buffett offloaded stakes in Wells Fargo and JPMorgan. Both stocks have since more than doubled.
  
  
• Blue Chip stamps: Once a booming business, the rewards program faded. But the float it generated enabled acquisitions like See’s and Wesco — a silver lining.
  
  
• Berkshire Hathaway (the textile mill): Buffett called it his “worst investment.” The failing business consumed capital until its closure in 1985. Ironically, it became the holding company for one of history’s greatest investing runs.
  
  

A legacy beyond the ledger Buffett’s genius wasn’t just in what he bought, it was in how he thought. From valuing competitive moats to championing patience and integrity, he rewrote the rules of long-term investing. As he prepares to pass the torch, the final tally includes iconic wins, instructive failures, and a fortune that grew not just in dollars, but in influence.