Top 14+ Times a Missed Deal Changed History

History often turns on seemingly small decisions—handshakes never completed, offers declined, or opportunities missed. These pivotal moments when deals fell through have shaped our world in ways that continue to reverberate today.

The ripple effects of these missed connections have altered political landscapes, technological development, and even entertainment as we know it. Here is a list of 14 remarkable instances when a missed deal or rejected offer dramatically changed the course of history, proving that sometimes what doesn’t happen matters just as much as what does.

The Louisiana Purchase Almost Didn't Happen

Napoleon Bonaparte initially had no intention of selling the Louisiana Territory to America. His original plan involved creating a massive French empire in North America, but military defeats and a slave rebellion in Haiti forced his hand.

When American diplomats arrived in France in 1803, they were authorized to offer $10 million just for New Orleans. Instead, they were surprised when France offered the entire territory—more than doubling the size of the United States for $15 million.

Had Napoleon stuck to his original plan or American negotiators hesitated, the geographic makeup of the United States would be drastically different today.

Nintendo Almost Partnered with Sony

In 1991, Nintendo and Sony announced a partnership to develop a CD-ROM add-on for the Super Nintendo. However, Nintendo abruptly backed out of the deal the very next day, announcing a partnership with Philips instead.

Furious at this public embarrassment, Sony executives decided to develop their own gaming console—the PlayStation. This rejected partnership transformed Sony into Nintendo’s biggest competitor and changed the gaming landscape forever, with PlayStation eventually becoming the best-selling console brand of all time.

Yahoo Could Have Bought Google

In 2002, Yahoo had the opportunity to purchase Google for $1 billion but declined, believing the price was too steep. Just two years later, Google’s value had skyrocketed, making the acquisition impossible.

By 2016, Yahoo—once the internet’s most valuable company—sold to Verizon for $4.8 billion, while Google transformed into Alphabet Inc., becoming one of the most valuable companies on the planet. This missed acquisition represents perhaps the most expensive business miscalculation in modern history.

Russia Selling Alaska

In 1867, Russia sold Alaska to the United States for $7.2 million—about two cents per acre. The Russian government viewed Alaska as a financial burden, difficult to defend, and with seemingly limited resources.

This perception changed dramatically when gold was discovered in the late 1890s, followed by oil in the 20th century. Russia’s hasty sale transferred incredible mineral wealth and strategic territory to the United States, a decision that Russian officials have lamented ever since.

Excite Could Have Bought Google

Before Yahoo’s missed opportunity, another internet company had an even cheaper chance at acquiring Google. In 1999, Excite CEO George Bell turned down Larry Page’s offer to sell Google for just $750,000.

Bell apparently thought the price was too high for a search engine that worked too well—Excite wanted users to spend more time on their site viewing ads. That decision allowed Google to develop independently and eventually dominate the internet landscape, while Excite faded into relative obscurity.

The Confederacy's Failed European Alliances

During the American Civil War, the Confederacy desperately sought recognition and military support from European powers, particularly Britain and France. Confederate diplomats nearly secured these crucial alliances, but several factors—including the Union’s Emancipation Proclamation, which transformed the war into an explicit fight against slavery—prevented formal agreements.

Had these deals materialized, the Confederacy might have gained international legitimacy and military support that could have altered the outcome of the war and the future of the American nation.

Blockbuster Declining to Buy Netflix

In 2000, Netflix founders approached Blockbuster with an offer to sell their fledgling company for $50 million. Blockbuster’s CEO reportedly laughed them out of the room. As streaming technology developed, Netflix pioneered the shift away from physical media while Blockbuster clung to its retail model.

By 2010, Blockbuster filed for bankruptcy protection, while Netflix grew into an entertainment powerhouse worth billions. This missed acquisition represents one of the most dramatic business reversals in modern corporate history.

The Ottoman Empire's Rejected Alliance Switch

During World War I, the Allied Powers made secret overtures to the Ottoman Empire, attempting to persuade them to abandon their alliance with Germany. These negotiations nearly succeeded at several points, but ultimately fell through.

Had the Ottomans switched sides, the war might have ended years earlier, potentially preventing millions of deaths and dramatically changing the map of the modern Middle East. The failed deal contributed to the eventual collapse of the Ottoman Empire and the problematic borders drawn by European powers afterward.

Kodak's Digital Camera Misstep

In 1975, Kodak engineer Steven Sasson invented the first digital camera, but the company’s executives rejected the technology, fearing it would threaten their film business. Despite holding many crucial patents in digital photography, Kodak failed to capitalize on its own innovation, missing the opportunity to lead the digital revolution.

This internal rejection of a transformative technology led to Kodak’s eventual bankruptcy in 2012, despite having had a multi-decade head start on what would become the standard for photography worldwide.

When Opportunity Knocks

Throughout history, these pivotal moments when deals were declined, partnerships dissolved, or opportunities missed have shaped our world in profound ways. From territorial acquisitions that redrew maps to business decisions that created tech giants, these 14 examples demonstrate how single decisions can cast long shadows across time.

The roads not taken often prove just as consequential as those followed—reminding us that history balances delicately on the edge of deals made and missed, constantly redirected by human choices that seemed insignificant at the time.