Heads or Tails? Famous Coin Flips That Changed History

Heads or Tails ! We have all been stuck between two choices, fingers nervously flicking a coin into the air, and surrendering our fate to the universe. But what if I told you that this humble act of flipping a coin has shaped the course of history? From founding cities to deciding Olympic medals, coin tosses have played starring roles in moments that altered lives, legacies, and even nations.

At coinflips.com.au, we’re all about embracing the power of chance, so let’s dive into the wild, weird, and downright pivotal coin flips that prove luck isn’t always random.

The Coin Toss That Named Portland, Oregon
How a gamble between two founders created a city.

In 1845, two entrepreneurial settlers Asa Lovejoy from Boston and Francis Petty grove from Portland, Maine found themselves at a crossroads. They owned the land that would become one of America’s most iconic cities, but they could not agree on a name. Lovejoy wanted “Boston,” Petty grove pushed for “Portland.”

Their solution? A best-of-three coin toss. Petty grove just happened to have a copper penny in his pocket, minted in his hometown. Two out of three flips landed as “Portland,” and the rest is history.

Fun twist: The “Portland Penny” is now displayed at the Oregon Historical Society. If you’re ever in town, you can see the coin that refused to let Boston steal the spotlight.

👉 Love a good origin story? Check out our guide The History of Coin Flips in Decision-Making.

The Olympic Basketball Final That Hinged on a Coin
When Team USA’s fate rested on pure chance.

The 1968 Summer Olympics Men’s Basketball final was a showdown between the U.S. and the Soviet Union, except it never happened. Instead, a bizarre semifinal tie between the U.S. and Puerto Rico led officials to use a coin toss to decide which team will advance.

The U.S. won the toss, but controversy erupted. Critics argued the Olympics should’ve used a point system, not chance. The Americans went on to win gold, but the incident sparked rule changes to avoid leaving medals to luck.

Lesson learned: Even the Olympics aren’t immune to the drama of a coin flip!

The NFL’s First Overtime Game (Thanks to a Coin)
How a 1958 coin toss created “The Greatest Game Ever Played.”

Before 1958, NFL overtime rules did not exist. When the Baltimore Colts and New York Giants tied in the championship, league officials scrambled. They flipped a coin to decide who would get the ball first in sudden-death overtime. The Colts called heads, won the toss, and scored a touchdown, cementing their legacy—and proving the power of a single flip.

Legacy: This game revolutionized football, leading to today’s overtime rules. Without that coin, we might never have seen Tom Brady’s legendary comebacks!

👉 Need a quick decision? Try our Instant Coin Flip Tool to resolve your own showdowns.

The $1 Coin That Divided Australia
The royal “tails” debate that sparked a national conversation.

In 1984, Australia redesigned its $1 coin, replacing Queen Elizabeth II’s portrait on the “tails” side with kangaroos. But when the Royal Australian Mint announced the change, traditionalists revolted. Critics argued the Queen’s absence was disrespectful, while others praised the nod to Aussie wildlife.

The Mint’s response? “It was decided by a coin toss, of course!” (Just kidding—but imagine if it had been!)

Trivia: Today, Australian coins still feature the monarch on the obverse (“heads”) and native designs on the reverse. A compromise? Maybe. But we like to think a coin flip could’ve solved the debate faster.

The Coin Flip That (Almost) Started a War
Or how a dictator used “heads or tails” to justify an invasion.

In 2003, U.S. General Tommy Franks reportedly flipped a coin to decide whether to invade Iraq from the north or south. While historians debate the truth of the anecdote, the story stuck as a symbol of how even life-and-death decisions can feel arbitrary.

Dark irony: Coins are meant to resolve conflicts, not create them. Let’s stick to using them for pizza toppings, shall we?

The Philosopher Who Flipped Coins for Love
When “heads or tails” decided a marriage.

In 1923, Argentine poet Jorge Luis Borges allegedly flipped a coin to choose between marrying two women. The coin landed on “heads,” sealing his fate with Norah Lange. While their marriage didn’t last, the story became a legend of romance-by-chance.

Our take: Maybe don’t use a coin flip for your wedding vows… but hey, it makes a great story!

Why Coin Flips Still Matter
These stories remind us that coin tosses aren’t just about leaving things to luck—they’re about embracing uncertainty. In a world obsessed with control, flipping a coin forces us to trust the journey, whether we’re naming cities or choosing takeout.

And let’s be honest: sometimes, the universe has better plans than we do.

Next Time You Can’t Decide…

Feeling inspired? Whether you’re naming your startup or settling a sibling rivalry, flip a coin with us and let history (or at least fun) repeat itself. Who knows? Your flip might just become tomorrow’s legendary tale.

Looking for more coin flip fun? Explore our guides on How to Use a Coin Toss for Life Decisions or The Science Behind Fair Flips.