Billionaire Warren Buffett's prestigious 60-plus-year career at the helm of Berkshire Hathaway delivered staggering returns for investors. Since Buffett started building his investment company in 1965, Berkshire's shares have soared more than 6,000,000 percent - compare that to the 46,061 percent gain for the benchmark S&P 500 over the same period. Buffett attributed his extraordinary success to roughly a dozen truly great decisions that he made over the course of his storied investing career. From turning a bet on Apple into billions to transforming a $1.3 billion investment in American Express into $56 billion, Buffett has built a reputation as one of the greatest investors in history. Now, as the 96-year-old prepares to step down and hand the reins to his son Howard, the Daily Mail takes a closer look at some of his biggest wins – as well as the investment Buffett himself called the worst decision of his life.

For decades, Buffett had a simple reason for staying away from technology stocks : He said that he didn't understand them well enough. Apple changed that. Berkshire Hathaway began quietly buying the company's shares in 2016, at a time when Apple was hardly an undiscovered startup. The iPhone was already a global phenomenon, but concerns about slowing sales had sent the stock tumbling. Berkshire's initial disclosure showed a stake of roughly $1 billion – a surprisingly small position for a company of its size, but still a significant departure for an investor who had largely kept his distance from tech. What Buffett saw was not really a bet on the next must-have gadget. He saw a product people were deeply attached to, with a customer base willing to keep coming back. That distinction would prove enormously valuable. Berkshire continued buying, eventually pouring $36 billion into Apple between 2016 and 2018.

By the end of 2023, the stake had ballooned to more than $174 billion – nearly five times what Berkshire had originally paid. The position became so large that Apple eventually accounted for an extraordinary share of Berkshire's stock portfolio . Berkshire has since sold down the investment, but Apple remained its largest disclosed stock position as of mid-2026, worth about $66 billion. It was a striking late-career reversal for Buffett, as the investor who spent years saying technology was outside his circle of competence. Instead, he had found one of his biggest winners in one of the world's most valuable tech companies.

Warren Buffett's bet on American Express began with a scandal that could have sunk the company. In 1963, the financial giant was caught up in what became known as the Salad Oil Scandal, after a commodities trader fraudulently used millions of dollars' worth of soybean oil as collateral for loans. The scandal sent American Express shares plunging as investors feared the company could be crushed by the losses - but Buffett saw something different. Rather than focusing on the immediate damage, he spent weeks studying the business and watching how customers reacted to the scandal. What he found convinced him that the company's most valuable asset had survived intact: its reputation. Buffett invested about $13 million in American Express, roughly 40 percent of his investment partnership's assets at the time.

It was a huge gamble, and he was betting that customers would continue trusting American Express even after the company's name had been dragged through one of the biggest financial scandals of the era. They did. The investment became one of the defining successes of Buffett's early career. American Express recovered, and Berkshire Hathaway's stake would eventually be worth between $46 and $56 billion. Buffett later described the episode as an important lesson in investing: A company's stock price can collapse without the underlying business being permanently damaged. It was also an early glimpse of the strategy that would define Buffett's career – looking past Wall Street's panic to figure out whether a company's most important asset had actually been lost.

Buffett found one of his greatest investments in a company whose biggest mistake was putting its most famous product at risk. Berkshire Hathaway began building its Coca-Cola position in 1988, spending about $1.3 billion to buy roughly 400 million shares. At the time, the investment looked less like a wild gamble than a bet on a brand Buffett had admired and consumed for years. Then Coca-Cola made a spectacular misstep. In 1985, the company replaced its original formula with a sweeter version dubbed New Coke , triggering a furious backlash from customers who demanded the return of the original drink. Coca-Cola eventually brought it back as Coca-Cola Classic, and by the time Buffett bought in, the New Coke fiasco was already behind the company - but the episode had demonstrated just how attached consumers were to a brand they loved. Berkshire held onto its Coca-Cola shares for decades as the investment grew into one of the company's signature holdings. The roughly $1.3 billion Berkshire spent buying the stock eventually turned into a stake that brought the company billions. The company also collected billions in dividends along the way, including $848 million in February 2026.

One of Buffett's most important deals had little to do with picking the next hot stock. In 1967, he turned his attention to the insurance business. Berkshire bought National Indemnity and National Fire & Marine from businessman Jack Ringwalt for about $8.6 million, giving Buffett control of a property-and-casualty insurance company. The deal would become enormously important for a reason that went far beyond insurance policies. Insurance companies collect premiums upfront, but may not have to pay claims for years. In the meantime, that money – known as the insurance float – can be invested. Buffett quickly recognized that Berkshire could use this pool of money to buy other businesses and investments while waiting for claims to come due.

Buffett had been buying shares of GEICO for years before Berkshire eventually took full control of the company in 1996. GEICO had caught his attention decades earlier because of its low-cost, direct-to-consumer model, and Buffett had first invested in the insurer in 1976 when it was in serious financial trouble. That early bet became another enormous success – and GEICO became one of Berkshire's most recognizable businesses, generating $6.8 billion in 2025 pretax earnings. This strategy helped transform Berkshire from a struggling textile manufacturer into the sprawling conglomerate it is today. The insurance business was generating the fuel. Buffett could then decide where to deploy it – whether that meant buying stocks, entire companies or simply letting the money compound.

Buffett did not initially want to pay what See's Candies was asking, but that hesitation turned out to be part of the lesson. Berkshire Hathaway bought the California candy maker in 1972 for about $25 million after being pushed by his late investing partner Charles Munger, a steep price by Buffett's standards at the time. But See's had something Buffett increasingly came to value: Customers who were willing to pay a little more for a product they trusted. The company had a loyal following and a powerful brand, allowing it to raise prices without losing its customers. That meant Berkshire did not have to pour huge amounts of money into factories, equipment or inventory to keep growing the business. Instead, See's could generate substantial cash that Buffett could then put to work elsewhere.

It paid off. By 2007, See's had generated $1.35 billion in pre-tax earnings for Berkshire, while requiring relatively little additional capital to expand. But the real value of the deal went beyond the candy. Buffett later credited See's with changing the way he thought about investing. He had previously focused heavily on buying businesses cheaply, even if their underlying economics were mediocre. See's helped convince him that paying a reasonable price for an exceptional business could be far more lucrative than buying a struggling company simply because it looked cheap. That idea would become central to Berkshire's strategy – and would help pave the way for some of Buffett's biggest investments in the years that followed.

Buffett has long pointed to Berkshire Hathaway's struggling textile business as one of his biggest mistakes. He took control of the Massachusetts-based textile manufacturer in 1965, hoping to turn around a business that had already been losing ground to cheaper foreign competition. Instead, the mill kept consuming capital and eventually closed in 1985. Yet there is a strong case that an even costlier mistake came later – and this time, Buffett's own Berkshire shares made the damage far worse. In 1993, Berkshire paid $433 million for Dexter Shoe Co., a Maine-based footwear manufacturer that Buffett believed had a durable competitive advantage. The problem was how he paid for it. Rather than hand over cash, Buffett gave Dexter's owners 25,203 Berkshire Class A shares – then worth about $433 million. The shoe company eventually collapsed under pressure from cheaper foreign competition, and Buffett later acknowledged that the deal had been a major error.

But the real sting came from what happened to the Berkshire stock he had surrendered. By 2007, Buffett calculated that those shares would have been worth about $3.5 billion. By 2014, he put the figure at roughly $5.7 billion – while Dexter itself had effectively become worthless. Buffett called Dexter his 'most gruesome' mistake, arguing that the loss was not simply the $433 million Berkshire had spent on a failed company. The far higher cost was the compounding value of the Berkshire shares he had given away. 'I gave away 1.6% of a wonderful business – one now valued at $220 billion – to buy a worthless business,' he said in a 2007 letter to investors. 'To date, Dexter is the worst deal that I've made.'