Most coin flips are over and forgotten in about two seconds. Who pays for lunch, who gets the sofa, who has to ring the landlord. But every so often two people with a lot on the line hand the decision to a coin, and the result ends up in the history books.

We went looking for the best examples. These are the three we keep coming back to, and we’d like to make this the first in a small series, because there are plenty more where these came from.

The penny that named Portland

In 1845 two men owned the land claim that would become Portland, Oregon. Asa Lovejoy was from Boston, Massachusetts. Francis Pettygrove was from Portland, Maine. Each wanted his own hometown on the map.

According to the Oregon Encyclopedia, they sorted it out over dinner at Francis Ermatinger’s house in Oregon City. Pettygrove dug an 1835 copper penny out of his pocket, and they agreed on two out of three: Lovejoy wins, it’s Boston. Pettygrove wins, it’s Portland. It went to a third toss before Pettygrove came out on top.

What we like about this one is how ordinary it was. Two men at a dinner table, one coin, and a city name that has now lasted nearly two centuries. The penny survived too. Pettygrove kept hold of it for years, and it eventually turned up in a family safe-deposit box before landing at the Oregon Historical Society around 1910, where it’s still on display as the Portland Penny.

It also shows why a flip can end an argument that talking couldn’t. They agreed the terms first, including best-of-three, so there was nothing left to dispute once the coin landed.

The toss at Kitty Hawk

On 14 December 1903, Wilbur and Orville Wright had their powered aircraft ready on the dunes of Kitty Hawk, North Carolina. There was one machine and two brothers who both wanted the first go, so they flipped a coin. The US National Park Service says Wilbur won.

His attempt didn’t work out. The aircraft got off the ground for a moment, then stalled and came back down. Three days later, on 17 December, it was Orville’s turn, and he made the first powered, controlled flight in history. It lasted about 12 seconds. They made three more flights that day, and Wilbur’s was the longest, at close to a minute.

The twist is that the winner of the toss didn’t get the famous flight. You could say Wilbur “lost” by winning, but that misses the point. A coin flip decides who goes first, nothing more. It can’t tell you who will do well. And the brothers clearly never held the toss against each other, because they shared credit for the whole project for the rest of their lives.

Hewlett or Packard first?

When Bill Hewlett and David Packard made their partnership official on 1 January 1939, they had a small but real problem. Whose name goes first? Hewlett-Packard and Packard-Hewlett both sound fine. According to HP’s own company history, they flipped a coin.

The company that grew out of a garage in Palo Alto went on to become one of the founding names of Silicon Valley, and the answer is printed on all of its products: Hewlett-Packard, or just HP.

We should be upfront about one thing. Accounts differ on which of the two men actually won the toss, and we couldn’t find a source we’d trust to settle it, so we’re not going to pick a version. What nobody disputes is that a coin made the call.

We think this is the most useful of the three for everyday life. It’s two equals, a decision that really doesn’t have a right answer, and a quick flip that stopped a new partnership from starting with an argument. Plenty of business disagreements deserve a coin more than they get one.

What these three have in common

Look at the stories side by side and a pattern appears. In every case there were two options that were genuinely about as good as each other. Both sides agreed to the coin before it was thrown. And both sides accepted the result afterwards, which is really the whole trick. A coin has no special power. It works because people promise in advance to live with what it says.

It’s also worth noticing that none of these flips were about picking the best option. Nobody was trying to predict anything. They just needed a fair way to move on.

Try it yourself

You don’t need an 1835 copper penny. If you’ve got two options and no good reason to prefer one, you can flip a coin right now with the Flip a Coin app. It can toss one coin or lots of them at once, it keeps a history of your results, and every flip is a true 50/50.

If you’ve got more than two options, the Spin the Wheel is probably a better fit, and the Randomfella home page has the rest of the free random tools. There are more guides on how fair randomness works too.

Sources: Portland Penny, Oregon Encyclopedia; Wright Brothers FAQ, US National Park Service; HP history, Bill and Dave, HPE; HP Garage, Wikipedia.