Which Major City Was Named by a Coin Toss?
Imagine a world where one of America’s most beloved Pacific Northwest cities was called Boston, Oregon instead. No Portland coffee culture. No “Keep Portland Weird.” Just… Boston West.
It almost happened. And the only thing that stood between that alternate reality and the Portland we know today was a single coin flip.
Two Men, One Plot of Land, One Big Disagreement
In 1843, two ambitious men arrived in the Oregon Territory with plans to build something lasting. Their names were Asa Lovejoy and Francis Pettygrove.
Lovejoy was from Boston, Massachusetts. Pettygrove hailed from Portland, Maine. Both had staked a claim to a densely forested stretch of land along the west bank of the Willamette River — land they believed had enormous potential as a future trading settlement.
By 1845, the land was cleared enough to establish a real town. There was just one problem: they could not agree on what to call it.
Lovejoy wanted Boston. Pettygrove wanted Portland.
Neither man would budge. So they did what reasonable men have done since the days of ancient Rome — they flipped a coin.
The Penny That Named a City
The coin they used was a large copper penny. The toss became known in Oregon folklore as the “Portland Penny” — and it remains one of the most famous coin flips in American history.
Pettygrove prevailed in the coin flip, and the town was named Portland.
Francis Pettygrove won. Portland, Oregon got its name — borrowed from a small coastal city in Maine — because of one lucky flip of a copper coin.
Asa Lovejoy went home empty-handed, his dream of a western Boston lost to chance.
What Happened to the Portland Penny?
The actual coin used in that flip survived. Today, the Portland Penny is preserved and on display at the Oregon Historical Society in downtown Portland. It is one of the most quietly significant artifacts in American urban history — a simple penny that determined the identity of an entire city.
If you visit Portland, you can see it in person. A coin no bigger than your thumbnail that shaped the name of a city now home to over 650,000 people.
Portland Today: What a Coin Toss Built
Portland, Oregon is now one of the most recognizable cities in the United States. Known for its craft beer scene, independent bookstores (Powell’s Books is the largest independent bookstore in the world), stunning natural surroundings, and famously quirky culture, Portland has carved out a powerful identity over nearly 180 years.
None of that identity would exist under the name “Boston.” The city’s entire brand, its nickname, its merchandise, its civic pride — all of it traces back to one man’s lucky coin flip in 1845.
Not the Only Time a Coin Toss Shaped a City
Portland is the most famous example, but coin flips have influenced place names and civic decisions more often than most people realize.
In early American settlement history, disputes over land, names, and boundaries were common — and formal legal systems were often far away. A coin flip was fast, fair, and final. It required no lawyer, no judge, and no negotiation. Just two people, one coin, and an agreement to accept the result.
That spirit of simple, unbiased decision-making is exactly what has made coin flipping endure for thousands of years — from ancient Roman streets to Oregon riverbanks to your smartphone screen.
The Lesson from Portland’s Penny
There is something deeply human about this story. Two intelligent, driven men — both with strong opinions, both with legitimate claims — reached a moment where logic and argument had run out. So they handed the decision to chance and agreed to live with the result.
No resentment. No legal battle. Just: heads or tails?
That kind of clean, instant decision-making is something we all need sometimes. Whether you are choosing between two job offers, two restaurants, or two vacation destinations — sometimes the fairest thing you can do is simply flip a coin and commit to the outcome.
It worked for Francis Pettygrove. It worked for Portland. It might just work for you.
References
Oregon Historical Society — The Portland Penny
https://www.ohs.org/museum/artifacts/portland-penny.cfm
History News Network — Coin Tossing Through the Ages
https://www.historynewsnetwork.org/article/coin-tossing-through-the-ages
Wikipedia — Portland, Oregon — History
https://en.wikipedia.org/wiki/Portland,Oregon#History
Smithsonian Magazine — How Portland Got Its Name
https://www.smithsonianmag.com/smart-news/how-portland-oregon-got-its-name-180948399/ Oregon Encyclopedia — Francis Pettygrove
https://www.oregonencyclopedia.org/articles/pettygrove_francis_w_1812_1887/
Powell’s Books — About
https://www.powells.com/info/about-powells