Markets
Warren Buffett’s Biggest Wins & Fails
Warren Buffett’s investing track record is nearly impeccable.
Over his lifetime, Buffett has built Berkshire Hathaway into one of the biggest companies in American history, amassed a personal fortune of over $80 billion, and earned acclaim as one of the world’s foremost philanthropists.
But in a 75-year career, it’s no surprise that even Buffett has made the odd blunder – and there’s one that he claims has ultimately costed him an estimated $200 billion!
The Warren Buffett Series
Part 4: Buffett’s Biggest Wins and Fails
Today’s infographic highlights Buffett’s investing strokes of genius, as well as a few decisions he would take back.
It’s the fourth part of the Warren Buffett Series, which we’ve done in partnership with finder.com, a personal finance site that helps people make better decisions – whether they want to dabble in cryptocurrencies or become the next famous value investor.
Note: New series parts will be released intermittently. Stay tuned for future parts with our free mailing list.
How did Buffett go from local paperboy to the world’s most iconic investor?
Here are the backstories behind five of Warren’s biggest acts of genius. These are the events and decisions that would propel his name into investing folklore for centuries to come.
Buffett’s 5 Biggest Wins
From making shrewd value investing calls to taking advantage of misfortune in the salad oil market, here are some of the stories that are Buffett classics:
1. GEICO (1951)
At 20 years old, Buffett was attending Columbia Business School, and was a student of Benjamin Graham’s.
When young Buffett learned that Graham was on the board of the Government Employees Insurance Company (GEICO), he immediately took a train to Washington, D.C. to visit the company’s headquarters.
On a Saturday, Buffett banged on the door of the building until a janitor let him in, and Buffett met Lorimer Davidson – the future CEO of GEICO. Ultimately, Davidson spent four hours talking to this “highly unusual young man”.
He answered my questions, taught me the insurance business and explained to me the competitive advantage that GEICO had. That afternoon changed my life.
– Warren Buffett
By Monday, Buffett was “more excited about GEICO than any other stock in [his] life” and started buying it on the open market. He put 65% of his small fortune of $20,000 into GEICO, and the money he earned from the deal would provide a solid foundation for Buffett’s future fortune.
Although Buffett sold GEICO after locking in solid gains, the stock would rise as much as 100x over time. Buffett bought his favorite stock again a few years later, loaded up further during the 1970s, and eventually bought the whole company in the 1990s.
2. Sanborn Maps (1960)
This early deal may not be Buffett’s biggest – but it’s the clearest case of Benjamin Graham’s influence on his style.
Sanborn Maps had a lucrative business around making city maps for insurers, but eventually its mapping business started dying – and the falling stock price reflected this trend.
Buffett, after diving deep into the company’s financials, realized that Sanborn had a large investment portfolio that was built up over the company’s stronger years. Sanborn’s stock was worth $45 per share, but the value of the company’s investments tallied to $65 per share.
In other words, these investments held by the company were alone worth more than the stock – and that didn’t include the actual value of the map business itself!
Buffett accumulated the stock in 1958 and 1959, eventually putting 35% of his partnership assets in it. Then, he became a director, and convinced other shareholders to use the investment portfolio to buy out stockholders. He walked away with a 50% profit.
3. The Salad Oil Swindle (1963)
For a value investor like Buffett, every mishap is a potential opportunity.
And in 1963, a con artist named Anthony “Tino” De Angelis inadvertently set Buffett up for a massive home run. After De Angelis attempted to corner the soybean oil market using false inventories and loans, the market subsequently collapsed.
American Express – the world’s largest credit card company at the time – got caught up in the disaster, and its stock price halved as investors thought the company would fail.
Although everyone else panicked, Buffett knew the scandal wouldn’t affect the overall value of the business. He was right – and bought 5% of American Express for $20 million. By 1973, Buffett’s investment increased ten times in value.
4. Capital Cities / ABC (1985)
In the 1980s, corporate raiders and takeover madness reigned supreme.
The massive TV network ABC found itself vulnerable, and sold itself to a company that promised to keep its legacy intact. Capital Cities, a relative unknown and a fraction of the size, had somehow managed to buy ABC.
The CEO of Cap Cities, Tom Murphy – one of Buffett’s favorite managers in the world – gave Warren a call:
Pal, you’re not going to believe this. I’ve just bought ABC. You’ve got to come and tell me how I’m going to pay for it.
– Tom Murphy, Capital Cities CEO
Berkshire dropped $500 million to finance the deal. This turned Buffett into Murphy’s much-needed “900-lb gorilla” – a loyal shareholder that would hold onto shares regardless of price, as Murphy figured out how to turn the company around.
It turned out to be a fantastic gamble for Buffett, as Capital Cities/ABC sold to Disney for $19 billion in 1995.
5. Freddie Mac (1988)
Buffett started loading up on shares of Freddie Mac in 1988 for $4 per share.
By 2000, Buffett noticed the company was taking unnecessary risks to deliver double-digit growth. This risk, and its short-term focus, turned Buffett off the company. As a result, at a share price close to $70, he sold virtually all of his holdings, enjoying a return of more than 1,500%.
I figure if you see just one cockroach, there’s probably a lot.
– Warren Buffett
Later on, Freddie Mac’s business would collapse in the housing crisis, only to be taken over by the U.S. federal government. Today, its stock sells for a mere $1.50 per share.
Buffett’s Blunders
Over the course of 75 years, it’s not surprising that even Buffett has made some serious mistakes. Here are his costliest ones:
1. Berkshire Hathaway (1962)
When Buffett first invested in Berkshire Hathaway, it was a fledgling textile company.
Buffett eventually tried to pull out, but the company changed the terms of the deal at the last minute. Buffett was spiteful, and loaded up with enough stock to fire the CEO that deceived him.
The textiles business was terrible and sucked up capital – and Berkshire unintentionally would become Buffett’s holding company for other deals. This mistake, he estimates, costed him an estimated $200 billion.
2. Dexter Shoes (1993)
Dexter Shoe Co. had a long, profitable history, an enduring franchise, and suberb management. In other words, it was the exact kind of company Buffett liked.
Buffett dropped $433 million in 1993 to buy the company, but the company’s competitive advantage soon waned. To make matters worse, Warren Buffett financed the deal with Berkshire’s own stock, compounding the mistake hugely. It ended up costing the company $3.5 billion.
To date, Dexter is the worst deal that I’ve made. But I’ll make more mistakes in the future – you can bet on that.
– Warren Buffett
Later on, Buffett would say that this deal deserved a spot in the Guinness Book of World Records as a top financial disaster.
3. Amazon.com (2000s)
Buffett says not buying Amazon was one of his biggest mistakes.
I did not think [founder Jeff Bezos] could succeed on the scale he has. [I] underestimated the brilliance of the execution.
– Warren Buffett
Given that Amazon has shot up in value to become one of the most valuable companies in the world, and that Jeff Bezos is by now the far richest person globally, it’s fair to say this whiff continues to haunt Buffett to this day.
Markets
How Disinflation Could Affect Company Financing
History signals that after a period of slowing inflation—also known as disinflation—debt and equity issuance expands.


How Disinflation Could Affect Company Financing
The macroeconomic environment is shifting. Since the second half of 2022, the pace of U.S. inflation has been dropping.
We explore how this disinflation may affect company financing in Part 2 of our Understanding Market Trends series from Citizens.
Disinflation vs. Deflation
The last time inflation climbed above 9% and then dropped was in the early 1980’s.
Time Period | March 1980-July 1983 | June 2022-April 2023* |
---|---|---|
Inflation at Start of Cycle | 14.8% | 9.1% |
Inflation at End of Cycle | 2.5% | 4.9% |
* The June 2022-April 2023 cycle is ongoing. Source: Federal Reserve. Inflation is based on the Consumer Price Index.
A decrease in the rate of inflation is known as disinflation. It differs from deflation, which is a negative inflation rate like the U.S. experienced at the end of the Global Financial Crisis in 2009.
How might slowing inflation affect the amount of debt and equity available to companies?
Looking to History
There are many factors that influence capital markets, such as technological advances, monetary policy, and regulatory changes.
With this caveat in mind, history signals that both debt and equity issuance expand after a period of disinflation.
Equity Issuance
Companies issued low levels of stock during the ‘80s disinflation period, but issuance later rose nearly 300% in 1983.
Year | Deal Value |
---|---|
1980 | $2.6B |
1981 | $5.0B |
1982 | $3.6B |
1983 | $13.5B |
1984 | $2.5B |
1985 | $12.0B |
1986 | $24.2B |
1987 | $24.9B |
1988 | $16.9B |
1989 | $12.9B |
1990 | $13.4B |
1991 | $45.2B |
1992 | $50.3B |
1993 | $95.3B |
1994 | $63.7B |
1995 | $79.7B |
1996 | $108.7B |
1997 | $106.5B |
1998 | $97.0B |
1999 | $142.8B |
2000 | $156.5B |
Source: Bloomberg. U.S. public equity issuance dollar volume that includes both initial and follow-on offerings and excludes convertibles.
Issuance grew quickly in the years that followed. Other factors also influenced issuance, such as the macroeconomic expansion, productivity growth, and the dotcom boom of the ‘90s.
Debt Issuance
Similarly, companies issued low debt during the ‘80s disinflation, but levels began to increase substantially in later years.
Year | Deal Value | Interest Rate |
---|---|---|
1980 | $4.5B | 11.4% |
1981 | $6.7B | 13.9% |
1982 | $14.5B | 13.0% |
1983 | $8.1B | 11.1% |
1984 | $25.7B | 12.5% |
1985 | $46.4B | 10.6% |
1986 | $47.1B | 7.7% |
1987 | $26.4B | 8.4% |
1988 | $24.7B | 8.9% |
1989 | $29.9B | 8.5% |
1990 | $40.2B | 8.6% |
1991 | $41.6B | 7.9% |
1992 | $50.0B | 7.0% |
1993 | $487.8B | 5.9% |
1994 | $526.4B | 7.1% |
1995 | $632.7B | 6.6% |
1996 | $906.0B | 6.4% |
1997 | $1.3T | 6.4% |
1998 | $1.8T | 5.3% |
1999 | $1.8T | 5.7% |
2000 | $2.8T | 6.0% |
Source: Dealogic, Federal Reserve. Data reflects U.S. debt issuance dollar volume across several deal types including: Asset Backed Securities, U.S. Agency, Non-U.S. Agency, High Yield, Investment Grade, Government Backed, Mortgage Backed, Medium Term Notes, Covered Bonds, Preferreds, and Supranational. Interest Rate is the 10 Year Treasury Yield.
As interest rates dropped and debt capital markets matured, issuing debt became cheaper and corporations seized this opportunity.
It’s worth noting that debt issuance was also impacted by other factors, like the maturity of the high-yield debt market and growth in non-bank lenders such as hedge funds and pension funds.
Then vs. Now
Could the U.S. see levels of capital financing similar to what happened during the ‘80s disinflation? There are many economic differences between then and now.
Consider how various indicators differed 10 months into each disinflationary period.
January 1981 | April 2023* | |
---|---|---|
Inflation Rate Annual | 11.8% | 4.9% |
Inflation Expectations Next 12 Months | 9.5% | 4.5% |
Interest Rate 10-Yr Treasury Yield | 12.6% | 3.7% |
Unemployment Rate Seasonally Adjusted | 7.5% | 3.4% |
Nominal Wage Growth Annual, Seasonally Adjusted | 9.3% | 5.0% |
After-Tax Corporate Profits As Share of Gross Value Added | 9.1% | 13.8% |
* Data for inflation expectations and interest rate is as of May 2023, data for corporate profits is as of Q4 1980 and Q1 2023. Inflation is a year-over-year inflation rate based on the Consumer Price Index. Source: Federal Reserve.
The U.S. economy is in a better position when it comes to factors like inflation, unemployment, and corporate profits. On the other hand, fears of an upcoming recession and turmoil in the banking sector have led to volatility.
What to Consider During Disinflation
Amid uncertainty in financial markets, lenders and investors may be more cautious. Companies will need to be strategic about how they approach capital financing.
- High-quality, profitable companies could be well positioned for IPOs as investors are placing more focus on cash flow.
- High-growth companies could face fewer options as lenders become more selective and could consider alternative forms of equity and private debt.
- Companies with lower credit ratings could find debt more expensive as lenders charge higher rates to account for market volatility.
In uncertain times, it’s critical for businesses to work with the right advisor to find—and take advantage of—financing opportunities.

Learn more about working with Citizens.

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