4 Coin Flips That Changed History

Rock-paper-scissors aside, flipping a coin has become the ultimate unbiased decision maker. Calling it in the air often settles friendly disputes over who gets the last slice of pizza or whether to go to the movies or bowling on Friday night. In honor of Flip a Coin Day (today!), here are four big decisions that came down to a simple question: Heads or tails?

1. A Coin Toss Named Portland, Oregon

The two New England natives who founded Portland—called The Clearing at the time—both vied for the bragging rights of naming the 640-acre locale after their respective hometowns. Pioneers Asa Lovejoy (of Boston) and Francis Pettygrove (hailing from Portland, Maine) split the site’s land claim, and settled the decision on a coin toss.

Pettygrove won the best two-out-of-three coin toss in the parlor of the Francis Ermatinger House in Oregon City and the rest is history. Portland was incorporated in 1849, and the copper one-cent piece, minted in 1835 and now dubbed the Portland Penny, is on display at the Oregon Historical Society Museum.

2. A Coin Toss Decided the First Flight

Wilbur Wright won the chance to make history when he won a coin toss against brother Orville in their camp at Kill Devil Hills, North Carolina, in 1903. Wilbur bested his brother in the coin toss for the first crack at flying on December 14, but in a twist of fate, Wilbur stalled the flyer in his first attempt, diving the flyer into the sand.

Three days later, after repairs, Orville was the first to get the contraption airborne at 10:30 on December 17, 1903. Wilbur, who won the coin toss fair and square, was immortalized in a photograph showing him running alongside the plane, very much grounded.

3. A Coin Toss Sealed Ritchie Valens’ Fate 

The blockbuster Winter Dance Party Tour (headliners: rock trailblazers Buddy Holly, Ritchie Valens, and J.P. “The Big Bopper” Richardson) stopped at the Surf Ballroom in Clear Lake, Iowa, a day before the music died. Holly chartered a plane for the tour’s next stop in Moorhead, Minnesota, after his tour bus was plagued with mechanical snafus. Richardson, suffering from the flu, convinced Holly band member Waylon Jennings to give up his seat, freeing up one more spot on the flight.

Tommy Allsup, a guitarist in Holly’s band, flipped a coin with Valens for the last seat, and lost the spot to the young Latin star. On February 3, 1959, the flight crashed into a cornfield after a one-two punch of piloting mistakes and poor weather conditions on a day Don McLean would remember as The Day the Music Died.

4. A Coin Toss Decided Secretariat’s Owner

The real story behind Secretariat starts in 1969, four years before the horse galloped its way to the Triple Crown. Penny Chenery of Meadow Stable and Ogden Phipps of Wheatley Stable flipped a coin for first pick of two foals sired by prominent racehorse Bold Ruler. Phipps won and picked a filly born from Bold Ruler and a mare named Hasty Matelda.

That left Chenery with the yet-unborn foal of Bold Ruler and Something Royal—a colt that would be named Secretariat at two years old, win the Triple Crown at three, and have a heart nearly four times the size of a normal horse. Secretariat’s performance at the Belmont Stakes ranks second on a list of the top 100 greatest individual sports performances ever, with only Wilt Chamberlain hitting the century mark surpassing it.

This post originally appeared last year.