The 7 Biggest Trading Mistakes in History

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Every business goes through ups and downs, but sometimes companies make decisions that lead to serious consequences. From the ill-fated mergers that were expected to synergize with stakeholders and lead to disruptions, to the launch of products with very high expectations that later faded in the physical market, to the loss of acquisition opportunities that caused giant companies to completely lose profits that could have been achieved.

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  • Kodak invented the first digital camera in 1975 but failed to commercialize it, missing out on a multi-billion dollar industry and contributing to the company's decline.
  • Yahoo passed on the opportunity to buy Google in its early stages, a decision that cost the company dearly as Google became a tech titan valued at nearly a trillion dollars.
  • The $36 billion merger between Daimler-Benz and Chrysler collapsed within a decade due to cultural clashes and poor integration, resulting in massive financial losses.
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  • Samsung’s Galaxy Note 7 fiasco, caused by faulty batteries, led to explosions, recalls, and eventual discontinuation, costing the company over $5 billion and harming its reputation.
  • In 1867, Russia sold Alaska to the U.S. for under $10 million, a decision now seen as a strategic blunder given Alaska’s vast natural resources valued at billions.
  • The Disney acquisition of Lucasfilm initially sparked mixed fan reactions but ultimately proved successful, generating massive profits through films, merchandise, and themed attractions.
  • The 2000 AOL-Time Warner merger, dubbed the "deal of the century," ended in failure due to management conflicts and unmet expectations, leading to nearly $100 billion in losses.

1. Kodak patents the first digital camera, and doesn't exploit the idea for decades

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Company involved: Kodak

Estimated total losses: more than $100 million*

In a stunning spectacle of missed opportunities, Kodak patented its first digital camera in 1975, but failed to capitalize on its groundbreaking invention. The company, known for its dominance of the film and photography industry, had a chance to revolutionize the market, but chose not to put that idea into practice.

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This fatal mistake was fatal for Kodak, as the advent of digital photography eventually led to the collapse of the company. While Kodak had the foresight to imagine the future of photography, its failure to adapt to and adopt digital technology ultimately left the company unable to catch up.

2. Empire returns the blow

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Companies involved: LucasFilm, Disney

Estimated total losses: More than $4.05 billion*

In one of the largest acquisitions in the history of the entertainment industry, Lucasfilm — the franchise owner of the popular Star Wars franchise — struck a deal with Disney in 2012. While many fans were excited about the future of Disney's Star Wars series, others were skeptical about how the merger would affect the beloved series.

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Eventually, Disney has already raised $1.5 billion from its new films in the Star Wars series, a figure that doesn't even include what it got from modern merchandise and profits from its Star Wars-themed theme park, i.e. Star Wars: Galaxy Edge:  Galaxy's Edge).

3. Daimler-Benz makes a bad deal

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Companies involved: Daimler-benz and Chrysler

Estimated total losses: $30 billion*

The merger of Daimler-Benz and Chrysler was once hailed as a historic deal that would create a strong entity in the automotive industry. But this was soon turned upside down. The merger in 1998 was challenged by cultural differences, administrative disputes and the failure to effectively integrate the two companies.

That merger did not even survive for a decade. In 2007, Daimler-Benz sold Chrysler for just $6 billion, a fraction of the original $36 billion it paid to buy the U.S. company 9 years earlier.

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4. Yahoo misses opportunity to buy Google at a low price

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Company involved: Yahoo

Estimated total losses: $990 billion*

In a plaything of fate, Yahoo found itself at a crossroads in the early 2000s, when it had an opportunity that could have completely changed its course. At the time, Google was on the verge of fateful things. However, Yahoo chose not to seize the opportunity, squandering a golden opportunity to acquire Google when its value was still rising.

This misstrategic move has put Yahoo in the position of a lamented observer, as it sees Google rise at rocket speed, becoming an online giant. This highlights the importance of recognizing latent opportunities and taking calculated risks in the business world.

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5. Russia sells America "last border" for less than $10 million

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Company involved: Russian Government

Estimated total losses: $37 billion*

Here we will discuss the captivating saga of Russia's unexpected move: the sale of Alaska to America in 1867. What seemed like an unlikely deal had far-reaching consequences. Russia's decision to give up that vast tract of land led to a marked turn in the course of history. This deal, with its symbols in terms of geopolitical dynamics, has reshaped borders and has always had lasting effects.

Russia has sold Alaska land to America for less than $10 million. Given that Alaska is so rich in resources, the sale of those lands in 1867 can only be described as a complete failure of the Russian government to see beyond the frozen surface of the "last frontier.

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6. Samsung Explosive Phone

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Company involved: Samsung

Estimated total losses: $5.3 billion*

In one of the most notorious product failures in recent memory, Samsung's Galaxy Note 7 has gone from being a smartphone with extremely high anticipation to a serious burden on those who own it. Shortly after its release in 2016, reports began to come in of cases of the Galaxy Note 7 exploding or catching fire.

The faulty battery design was later found to be the cause of the fault, but by that time, it was too late to repair the damage. After the company initially tried to downplay the problem and address it by recalling the product, Samsung finally decided to stop production of this model completely. The accident cost Samsung an estimated $5 billion in losses and severely damaged the company's reputation.

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7. Time Warner and AOL conclude the "deal of the century"

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Companies involved: AOL, Time Warner

Estimated total losses: $98.7 billion*

In one of the most talked about mergers in business history, in 2000 AOL merged with Time Warner in a deal valued at $350 billion. This partnership combined the power of the internet with the media giant; it looked like a heavenly sponsored operation.

At the time, this deal was hailed as a groundbreaking deal that would create a powerful media and technology conglomerate. But the merger fell short of high expectations, as senior officials at both companies were unable to agree on how to manage things or what to focus on in the business.

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