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Heads or Tails

Updated: Oct 22, 2023

The Big Portland Coin toss, you win if it is lands on heads and the city name will be Portland, Oregon, if it is on tails, it will be then it is Boston, Oregon.

1843.(or Maine) 1786, The city was officially founded in 1843 and its name was famously determined by the 1845-coin toss of a penny between business partners Asa Lovejoy (of Boston, Mass.) and Francis Pettygrove (of Portland, Maine).

One of its original names in the 1830s to the early 1840s, traders and settlers officially who referred to the new Portland as “The Clearing” due to the huge amount of trees in the area.

In 1845, Pettygrove and Lovejoy agreed to turn the site into a city. What they could not agree on, however, was what it would be named. Boston-bred Lovejoy wanted it to be named after Boston, while former Portland, Maine resident Pettygrove wanted it to be named after his own hometown.

A coin-toss would settle their differences. One night over dinner, Pettygrove and Lovejoy flipped a coin three times to choose the new territory’s name.

On the strength of luck, founder Pettygrove won after the coin landed on ‘heads’ twice., hence, Portland, Oregon.

Of course, they could have left the existing name and today it would likely be Stumptown, Oregon.

For all you flippers:

Bye-the-bye: A spinning penny will land tails side up roughly 80 per cent of the time. This is because the heads side of the penny, the one with Lincoln on it, is slightly heavier than the tail side.

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