Warren Buffett’s Five Biggest Investment Wins—and His Worst Deal Ever

Billionaire Warren Buffett’s more than six-decade tenure leading Berkshire Hathaway produced extraordinary returns for investors.

Since Buffett began building the investment company in 1965, Berkshire’s shares have surged by more than 6,000,000 percent. Over the same period, the benchmark S&P 500 gained 46,061 percent.

Buffett has said that his remarkable record was driven by roughly a dozen genuinely great decisions made throughout his celebrated investing career.

Those wins include turning an investment in Apple into billions and transforming a $1.3 billion stake in American Express into $56 billion, cementing Buffett’s reputation as one of history’s greatest investors.

Now, as the 96-year-old prepares to step aside and pass Berkshire Hathaway’s leadership to his son Howard, Our News Outlet examines some of his most successful investments — along with the decision Buffett once described as the worst of his life.

1. Apple  

For years, Buffett avoided technology stocks for a straightforward reason: He believed he did not understand the sector well enough.

Apple proved to be the exception.

Berkshire Hathaway began quietly accumulating Apple shares in 2016, when the company was already a global powerhouse rather than an overlooked startup.

The iPhone had already become a worldwide phenomenon, but fears over slowing sales had driven Apple’s stock lower.

Berkshire’s first disclosure revealed a stake worth about $1 billion. Although modest for a company of Berkshire’s size, the investment represented a major shift for Buffett, who had generally kept his distance from technology stocks.

Buffett was not simply betting on the next popular gadget. He recognized that customers were deeply loyal to Apple’s products and willing to return to the brand repeatedly.

That insight would become immensely profitable.

Berkshire continued buying Apple, investing $36 billion in the company between 2016 and 2018. By the end of 2023, the stake had grown to more than $174 billion — almost five times Berkshire’s original investment.

The holding eventually became an unusually large part of Berkshire’s stock portfolio. Although Berkshire has since reduced its position, Apple was still its largest disclosed stock investment as of mid-2026, valued at approximately $66 billion.

The investment marked a dramatic late-career change for Buffett. After years of insisting that technology fell outside his circle of competence, he found one of his biggest successes in one of the world’s most valuable technology companies.

2. American Express

Buffett’s American Express investment began with a scandal that threatened to bring the company down.

In 1963, the financial giant became embroiled in what was known as the Salad Oil Scandal. A commodities trader had fraudulently used millions of dollars’ worth of soybean oil as collateral to secure 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.

3. Coca-Cola

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.

4. National Indemnity, National Fire & Marine and GEICO

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.

5. See’s Candies

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.

Warren Buffett’s worst decision

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.’