Warren Buffett’s Retiring: His Best and Worst Investments Through the Years

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In early May, Warren Buffett, the “Oracle of Omaha” and GOAT (greatest of all time) of investing, announced to his board that he would be stepping down as CEO of Berkshire Hathaway on the last day of 2025. Despite Buffett being 94 years old and his intention to remain as chairman of the board, it was a shock to all. The man has run the investment company for 60 years.

In that time, Buffett has had a seeming Midas touch when it comes to picking companies that not only make money, but make billions from millions. In reality, however, not everything Buffett buys turns to gold. Here are Buffett’s biggest winners and biggest blunders.

Worst Mistakes

Berkshire Hathaway

Yes, Buffett himself has called this buy a bad one. That’s because when Buffett bought it in 1965, it was a struggling textile company which he bought more on emotion than logic — breaking his own investing rule. Over the years, of course, Buffett reinvented Berkshire into one of the most successful investment firms in the nation, making him one of the richest men on the planet.

Amazon

How could buying Amazon be a blunder, you ask? By passing it up for years. Buffett had a chance to buy Amazon early on, but, according to him, he didn’t understand Amazon’s business model well enough to pull the trigger. Still, better late than never and the online giant has been a big winner for Berkshire.

Tesco

You probably have never heard of British grocery chain Tesco and Buffett likely wishes he never had either. Buffett invested in the chain, was slow to get out when trouble arose and ended up losing $444 million, according to the Observer.

Dexter Shoe Co.

Another company you’ve likely never heard of. And another Buffett wishes he hadn’t bought, calling it his “most gruesome” mistake. According to Investopedia, Buffett paid $433 million for it in 1993 only to watch the shoe company fail soon after. The worst part was that Buffett paid for the company with Berkshire Hathaway stock. So, by 2020, the stock he gave up for the company would have been worth $12 billion.

Biggest Wins

Coca-Cola

Buffett bought Coca-Cola in 1988 and stuck with the drink giant through good times and bad, when healthier living threatened the sugary treat. Buffett’s belief in businesses with solid fundamentals has paid off with Coke. Since he bought stock in the company, it’s increased by over 3,500%, according to The Economic Times. Today, Berkshire Hathaway owns 9.3% of the global behemoth, per Kiplinger. 

American Express

Buffett first bought into American Express in the 1960s, then bought more through to the 1990s. Today, Berkshire Hathaway owns 21% of the company or about $44 billion worth. The company went public in 1977 and since then has increased over 100 fold.

Apple

A little late to the Apple party, Buffett didn’t buy the tech giant until 2016. Despite that, Apple has been Berkshire Hathaway’s biggest winner. As reported by the Observer, the company’s initial $35 billion investment grew to $173 billion by 2023. Buffett has since sold off quite a bit of its stock, but Apple remains the company’s largest holding, representing over 28% of Berkshire Hathaway’s holdings and worth $75 billion.

See’s Candies

According to See’s Candies website, Buffett and his late business partner, Charlie Munger, bought See’s Candies in 1972 after founder Laurance A. See passed away. The pair had long admired the business and, it turns out, for good reason. They bought the company for $25 million — it has returned $1.6 billion. That’s a pretty sweet deal.

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