Top 20 Most Expensive Mistakes In History

#20: Heavy Submarine (2013)

Maybe they are designed to reach astonishing depths, but thats no good if your submarine is incapable of surfacing again. Thats exactly what happened to the doomed Isaac Peral class of Spanish submarine when designers realized that somebody at some point had carelessly left a decimal point in the wrong place. The sub was 100 tons heavier than it should be, meaning that if it submerged, it would never be able to return to the surface. Thankfully, the sub hadnt yet been built, so the schematics were changed to make it longer and capable of supporting all that extra weight. Except, then there was another problem: the sub was now too large to fit into the port where it was being constructed.

#19: New Coke (1985)

In 1985, about a century after Coca-Cola first hit shelves, Coke decided to mix things up and rework the tried-and-tested Coke formula. The result was New Coke, one of the biggest marketing fails and disasters of all time. The simple fact was that nobody really liked New Coke. Coke wanted to make its drink taste more like Pepsi, which is a little sweeter than Coke, and it was a resounding failure. Though we understand trying to corner Pepsis share of the market, consumer capitalism is about choice; nobody wants to choose from two identical colas. There was just no reason for Coke to try and destroy its own business by changing the recipe.

#18: Ronald Wayne Sells Out (1976)

Hindsight is 20-20, which is why this error stings so much. Back in 76, businessman Ronald Wayne met Steve Jobs and Steve Wozniak and initially thought they had something with their fledgling computer company. Wayne went in with a 10% stake in Apple, but it wasnt to last: less than two weeks on and hed lost faith, selling those shares back to the companys founders. As we all know, Apple went on to become one of the biggest companies and electronic manufacturers in the entire world, with over a billion active iPhones as of 2021. What we wouldnt give for a time machine to the 70s so we could invest in the Apple shares Ron Wayne gave up!

#17: Wrong Trains (2014)

Weve seen submarines too big for their ports, but what about trains too wide for their platforms? Thats what happened in France in 2014 when Frances national rail company SNCF put in an order for 2000 brand-new trains. The trains would fit many big, metropolitan stations like Pariss newer infrastructure, but in rural France, the platforms were too narrow. This all happened because somebody at the French Rail Network gave SNCF the wrong measurements. SNCF was left trying to secretly widen the affected stations, but eventually, the error was made public. The trains themselves cost around $20 billion and modifying the platforms has cost over $60 million.

#16: Lost Bitcoin (2009)

Unlike so many current investors, James Howells wasnt chasing a Bitcoin trend. He was a lifelong computer geek who saw real promise in decentralized currency after the 2008 financial crash. So in 2009, he mined 8,000 Bitcoin, back when it was mostly discussed on obscure forums. Years later, assuming the hard drive was junk, he tossed it during a house cleanup. By the time Bitcoin hit mainstream value, that trash contained a digital treasure worth hundreds of millions at its peak. He has begged to excavate the Newport landfill ever since. He has offered robots, funding, and a full recovery plan. But the city keeps saying no. So for now, a near-billion-dollar mistake is still buried under banana peels and coffee grounds.

#15: Russia Sells Alaska (1867)

Its easy to look at a map of North America and wonder why Alaska, isolated as it is on Canadas western coast and completely separated from the US mainland, is one of the United States. But its been that way since the 1860s when the territory then controlled by the Russian Empire was sold by Tsar Alexander II to America for the low low price of $7.2 million. Today, thats over $130 million, which is still a paltry sum when you consider how large and valuable Alaska is, what with its many oil fields. The reason the territory was sold was to recoup losses from the Crimean War, and because Russia doubted it would be able to defend Alaska from invasion anyway.

#14: Quaker Buys Snapple (1994)

In the early 90s, Snapple was only on the up; it had a few high-profile ad campaigns that meant it was able to hold its own in the competitive world of juice and soft drinks, making it look like a promising investment opportunity for Quaker Oats. Unfortunately, things didnt go to plan; though Quaker Oats spent $1.7 billion on a deal it thought was a sure thing, after only three years Snapple was sold off again so that Quaker Oats could lick its wounds, for a meager $300 million. Perhaps a little embarrassingly, Snapple is still going strong. It seems that separating was the best thing for both of these brands.

#13: Star Wars Billions (1977)

In the mid-70s, nobody knew that Star Wars was going to become one of the biggest pop-culture properties in history. Production was expensive, difficult, and ran George Lucas into the ground. Not seeing its potential, 20th Century Fox made a deal with Lucas that hed receive the royalties from merchandise sales. What followed set a new standard for merchandisable franchises, giving Lucas a personal fortune to the tune of billions of dollars. It was a grave error on the part of Fox, and saw the studio miss out on an absolutely obscene amount of money in the decades between Star Wars release in theaters and Lucasfilms being acquired by Disney.

#12: Morgan Stanley's Losses (2007)

Morgan Stanley deserves a bit of credit. Unlike many on Wall Street, they saw the writing on the wall back in 2007. They saw the crash coming - and still got wrecked. Thats the magic of bad timing. The firms traders spotted early signs of the subprime collapse and bet against the market. Smart, right? Then they sold the winning bet and plowed back into risky mortgage-backed junk. Boom - $9 billion vanished. It was the biggest loss in the firms history. CEO John Mack later admitted they didnt understand how toxic the assets really were. They were right... until they werent. One financial writer called it the worst trade of 2007.

#11: California's High Speed Rail Boondoggle (1982-)

California promised a bullet train. What it delivered was a billion-dollar money pit on rails. First proposed in 1982, the project gained real momentum in 2008. Voters approved a nearly $10 billion bond to connect San Francisco and L.A. with 220 mph trains. Nearly twenty years later, there's no train, no full route. Californians were just left with a price tag thats ballooned to over $100 billion. Entire segments have been delayed, downsized, or abandoned. Lawsuits, land disputes, NIMBYism, political infightingyou name it. As recently as June 2025, the project has seen setbacks thanks to an unfriendly White House. At this point, the only thing moving at high speed is the budget.

#10: Brazil's World Cup Improvements (2014)

Brazil dropped $11.6 billion to host the 2014 World Cup: more than any country had ever spent. The pitch? A world-class tournament with sleek airports, modern trains, and long-term infrastructure gains. Brazil utterly failed to deliver. Brazil built a few shiny stadiums, sure, but left a trail of broken promises. Over $3.5 billion worth of planned upgrades were scrapped or never finished. One venue became a bus lot. Others sit mostly empty, collecting rust and regret. These days, its practically common knowledge: hosting mega-events like the World Cup or Olympics often leaves countries with more debt than glory. Brazil didnt just lose on the pitch; they lost in the ledgers.

#9: Fukushima Daiichi Nuclear Disaster (2011)

In 2011, a massive earthquake and tsunami rocked Japan. It triggered one of the worst nuclear disasters in history. But heres the kicker: it wasnt just nature. It was negligence. The Fukushima Daiichi plant was built on a known fault line. Backup generators were placed in low-lying areas, almost begging for flood damage. They could have spent a little more money during construction to build the plant more safely. They didn't. When the tsunami hit, the cooling systems failed. Three reactors melted down, and radioactive material spilled into the air and sea. The cleanup is still ongoing, costing over $200 billion and counting. Fukushima is a textbook example of short-term thinking and greed leading to long-term consequences.

#8: Tiger Woods' Affairs (2009)

At the height of his career, Tiger Woods was as much a global brand as golf legend. But in 2009, everything came crashing down. The money and the glam went to his head, and he stepped out on his wife. When news of his affairs broke, his reputation imploded. Woods' marriage collapsed on magazine covers and televisions across the globe. Tiger's sponsors ran for the hills. The star lost an estimated $12 billion in endorsements, tournament revenue, and brand value. Nike stuck with him, but others like Gatorade, AT&T, and Accenture bailed fast. It was one of the most expensive personal spirals in sports history. Tiger eventually made a comeback, but the fallout never went away.

#7: Dubai Aquarium Leak (2010)

Leave it to Dubai to build one of the worlds largest indoor aquariums inside a $20 billion shopping mall. It is a perfect symbol for capitalistic excess, taken down by a small leak. In 2010, the massive acrylic panel holding back about 10 million liters of water and thousands of marine animals started leaking. Shoppers were evacuated, water flooded the high-end shops, and panic set in as engineers rushed to contain the damage. The aquarium was repaired, but not before the leak made headlines worldwide. No full cost was ever revealed, but experts estimate the damage and downtime hit the tens of millions. Proof that even a little crack can cause a luxury-sized mess.

#6: Daimler-Chrysler Merger (1998)

When German auto-giant Daimler merged with Americas Chrysler in 1998, it was billed as a $36 billion marriage made in heaven. As it turned out, it was more along the lines of a drunken drive-through wedding in Las Vegas. The two companies clashed on everything from culture and strategy to management. Chryslers performance tanked, and morale plummeted. Daimler slowly realized it had bought itself a major headache. By 2007, they sold off 80% of Chrysler for a measly $7.4 billiona staggering loss of nearly $29 billion. What was supposed to be a global powerhouse became a business school case study in how not to do a merger.

#5: Deepwater Horizon Oil Spill (2010)

In 2010, BP tried to save time and money on a deepwater drilling project. Instead, they triggered one of the worst environmental disasters in history. The Deepwater Horizon oil rig exploded in the Gulf of Mexico, killing 11 workers and gushing over 200 million gallons of crude oil into the ocean. The spill lasted 87 days. Coastlines were wrecked, wildlife devastated. Cleanup and legal costs ballooned to around $65 billion. BP became the most hated company in the world's most hated industry overnight. Their reputation has yet to recover. When you value profit over safety, it's always a short-term bet. It takes one disaster to cost you all the money you've saved.

#4: AOL Buys Time Warner (2000)

In the year 2000, the Dot Com Bubble was at its height and it didnt look like anything would slow down the meteoric rise of the internet. Ultimately, the internets development didnt slow down, but the stock market did, leading to a recession. One of the biggest casualties was the merger of AOL and Time Warner in 2000, which even at the time was viewed by many as being a ridiculous idea. AOL spent a whopping $182 billion on merging with Time Warner, but years on, the companies split again. Today, Time Warner remains a major player in the media business, and while AOL still exists, its dead in the water. How the tables turned.

#3: Blockbuster Doesnt Buy Netflix (2000)

In 2000, Netflix was a scrappy DVD-by-mail service, losing money fast. Their dreams collapsing around their heads, co-founders Reed Hastings and Marc Randolph walked into Blockbuster HQ. They practically begged for a $50 million buyout. Blockbuster responded by laughing them out of the room. Within a decade, Blockbuster went bankrupt. Meanwhile, Netflix rewrote the rules of home entertainment. They eventually pivoted to pioneering the streaming space. Netflix created its own original content, soon dominating the world. Today, Netflix is worth over $150 billion. Its one of the coldest missed shots in business history. Blockbuster could have become the future of entertainment. Instead, they were left on the trash heap.

#2: Apollo 13 (1970)

The basis of a blockbuster movie starring Tom Hanks, Apollo 13 was destined for the moon in 1970 but it never made it. Thankfully, unlike many other space failures like the high-profile Challenger and Columbia disasters in 1986 and 2003 respectively, the astronauts in Apollo 13 all survived. The problem was that an oxygen tank had been damaged long before its installation in the spacecraft, which was described as a bomb by Commander Jim Lovell. That bomb went off, severely damaging the craft when it was already in space. The crew had to move into the lunar module so they would survive and then loop around the moon to return to Earth.

#1: Chernobyl (1986)

In 1986, the biggest nuclear disaster on record was triggered. The Soviet Union was initially extremely secretive about what had happened, with many downplaying the severity of the meltdown even when nuclear fallout spread as far west as Germany. But eventually, the truth came out, and it was revealed that a slew of errors was to blame for Chernobyl, making it an entirely avoidable tragedy. It was the human error of the unprepared shift workers combined with a fatal design flaw that was known about, but not fixed. The problem was that the control rods, made of boron, had graphite tips, and the graphite reacted with the core to cause the explosion. Without the cheap graphite, the disaster wouldnt have happened.

Do you know of other instances where big shots went bust? Let us know in the comments below!