The short version
Coin flips have settled everything from city names to who got the first pick of a future champion. These are some of the best-documented examples. As with many old stories, small details change from one telling to the next, so treat exact wording as approximate.
Naming Portland, Oregon (1845)
Two founders of a new settlement on the Willamette River, Asa Lovejoy and Francis Pettygrove, could not agree on a name. Lovejoy, from Massachusetts, wanted Boston. Pettygrove, from Maine, wanted Portland. They settled it with a coin toss, and Pettygrove won. The coin, a one-cent piece, is now known as the Portland Penny and is kept by the Oregon Historical Society.
Who flies first: the Wright brothers (1903)
When Wilbur and Orville Wright were ready to try their powered aircraft in December 1903, they tossed a coin to decide who would take the first attempt. Wilbur won, but his attempt on 14 December stalled and the plane was slightly damaged. Three days later, on 17 December, Orville made the first successful powered flight, lasting about 12 seconds.
The NBA draft coin flip (1966 to 1984)
Before the draft lottery began in 1985, a coin flip between the two teams with the worst records decided who got the first pick. Several famous careers began this way. In 1969, Milwaukee won a flip and chose Lew Alcindor, later known as Kareem Abdul-Jabbar. In 1979, the Lakers won a flip and picked Magic Johnson. In 1984, Houston won and took Hakeem Olajuwon.
A seat on a plane (1959)
On 2 February 1959, musician Ritchie Valens and guitarist Tommy Allsup tossed a coin for the last seat on a small plane. Valens won. The plane crashed the next morning, killing everyone on board, including Buddy Holly and J. P. Richardson. The flip has been remembered ever since as one of the most haunting in history.
Secretariat's breeding rights (1969)
Owners Penny Chenery and Ogden Phipps had a standing deal on foals from two mares, with a coin flip deciding who got first choice each year. Phipps won the 1969 toss and chose the other foal. Chenery received the colt that became Secretariat, who won the Triple Crown in 1973 and set records that still stand.
What these stories have in common
- Both sides agreed to the rule first. A coin flip only feels fair when everyone accepts it beforehand.
- A fair coin does not know how big the decision is. The odds were 50/50 each time, whether the stake was a seat or a city's name.
- Outcomes feel bigger afterwards. We remember the flips that led to something dramatic, and forget the thousands that decided nothing.
Want to settle something yourself?
Use the decision maker coin or the coin flip for a fair, instant answer. To read how the practice began, see the history of the coin toss.
Last updated 2026-10-18.