Important decisions usually arrive with meetings, arguments, paperwork, and people carefully weighing every possible outcome. History, however, has never been quite that orderly. Sometimes two choices appeared equally reasonable, a contest ended in a perfect tie, or nobody could agree on who deserved the next opportunity. When discussion failed, someone reached into a pocket and produced a coin. A few of these flips decided little more than whose name would appear first. Others influenced professional sports, political careers, popular music, aviation, and the identity of an American city. The people involved could not have known what would follow. To them, the coin was simply a quick and fair way to move forward. Looking back decades later, its brief journey through the air can feel like the most important part of the story.
#1: Portland’s Name Hinged on a Simple Coin Toss
A riverfront settlement in the Pacific Northwest came surprisingly close to becoming Boston, Oregon. In 1845, landholders Asa Lovejoy and Francis Pettygrove disagreed over what their growing community should be called. Lovejoy wanted to honor Boston, Massachusetts, while Pettygrove preferred the name of Portland, Maine. Instead of spending months arguing, they settled the question with a best-of-three contest using an 1835 copper penny. Pettygrove won two flips, placing Portland on future maps and leaving Boston as one of the region’s great “what might have been” stories.
