A coin flip is a tiny event — a metal disc, a thumb, a second of gravity. But some coin flips have carried enormous consequences. They decided who flew first, who got a city, who drafted the best player of a generation. They settled wars in miniature. Here are eight coin flips that actually changed history, with the stakes, the outcomes, and the what-ifs of each.
1. The Wright Brothers, Kitty Hawk, December 1903
On December 14, 1903, Wilbur and Orville Wright prepared the first controlled powered flight of a heavier-than-air machine. Both brothers wanted the honor of being first to fly. To decide, they flipped a coin. Wilbur won. He took the first attempt — and stalled the aircraft, damaging it on takeoff. It took three more days to repair.
On December 17, Orville took the second attempt and successfully flew for twelve seconds over 120 feet. Because of the coin flip, history remembers Orville Wright, not Wilbur, as the first human to pilot a powered airplane. A different toss and the textbooks read differently forever. Wilbur is forever the brother who flipped first and crashed. A sobering lesson that winning the coin flip is not the same as winning the event.
2. Portland versus Boston — the 1984 NBA Draft
Before the NBA introduced the Draft Lottery in 1985, the top pick was decided by a literal coin flip between the two worst teams in the league. On May 22, 1984, the Houston Rockets and Portland Trail Blazers met in what remains one of the most consequential coin tosses in sports history. The Rockets won the flip and took the first pick: Hakeem Olajuwon, who would become one of the greatest centers to ever play.
Portland, with the second pick, took Sam Bowie over a young shooting guard from North Carolina named Michael Jordan. Chicago, picking third, took Jordan. Bowie had an injury-ravaged career. Jordan became arguably the greatest basketball player ever. If Portland had won the flip, they would likely still have taken Olajuwon over Jordan, and Chicago's sixth championship — and entire late-1990s sports monoculture — would belong to a different city.
The NBA introduced the lottery the following year, explicitly to prevent any more single-flip decisions from reshaping the sport. Bowie-over-Jordan is the reason the lottery exists.
3. The naming of Portland, Oregon — 1845
Two New Englanders, Asa Lovejoy of Boston and Francis Pettygrove of Portland, Maine, jointly owned the land that would become Oregon's largest city. They disagreed on what to name it. Each wanted to honor his hometown. On a February day in 1845, they flipped a copper penny, best two out of three. Pettygrove won. The city was named Portland.
The coin, nicknamed the "Portland Penny," is now on display at the Oregon Historical Society in downtown Portland. It is a small one-cent piece, worn smooth from being held. If Lovejoy had won, Oregonians today would live in the city of Boston — and a lot of map software would be deeply confused.
4. The Super Bowl coin toss — every year since 1967
The most-watched coin flip in the world is the Super Bowl kickoff toss, performed before every game since Super Bowl I in 1967. The toss decides who kicks off first. In theory it should be 50/50. In practice, as of Super Bowl LVIII, the NFC had won the toss 28 times out of the first 58 Super Bowl tosses. That is just under 50% — a textbook illustration that small sample sizes always look a little uneven even when the process is perfectly fair.
The Super Bowl coin is a special commemorative piece minted in gold-plated silver for each year's game, then retired to the Pro Football Hall of Fame in Canton, Ohio. It has become a ritual object in its own right — the actual weight of chance that begins every championship.
A curious statistical note: teams that win the Super Bowl coin toss have actually won the game less than half the time. Winning the coin toss historically lets you choose to receive the ball, but choosing to receive first often means the opponent gets the ball after halftime — which in modern NFL play is a measurable advantage. So the coin toss appears to punish the obvious choice. The smart move now is to defer.
5. The U.S. presidency — Warren G. Harding, 1920
Less well-verified, but widely-cited, is a story about the Republican National Convention of 1920. Deadlocked after multiple ballots, party leaders retreated to a smoke-filled room at the Blackstone Hotel in Chicago. According to some accounts, they considered multiple candidates and — after an evening of indecision — flipped a coin as part of the final selection process that landed on Warren G. Harding.
Historians dispute the exact role of the coin (the decision involved much more than one flip), but the phrase "smoke-filled room" entered the English language from that night. Harding went on to win the general election and die in office two years later, presiding over one of the most corruption-plagued administrations in US history. The coin, if real, picked a bad one.
6. Buddy Holly's plane seat — February 3, 1959
After a show in Clear Lake, Iowa, musicians Buddy Holly, Ritchie Valens, J. P. Richardson ("The Big Bopper"), and Waylon Jennings were booked on a small charter plane to the next gig. The plane only had four seats. There was a dispute over who would fly versus ride the cold tour bus. Ritchie Valens had never flown before and wanted to. He and Holly's guitarist Tommy Allsup flipped a coin for the last seat. Valens won.
The plane crashed shortly after takeoff, killing all four people aboard. The event became known as "the day the music died." If the coin had gone the other way, Ritchie Valens — 17 years old, with one year of hit records behind him — would likely have lived and continued one of the most promising careers in rock and roll. A different flip and La Bamba's author builds a forty-year career. The flip decided who made it to 1960.
7. Denver versus Seattle — the 1968 US coin design
In the strangest meta-coin-flip on this list, the US Mint in 1968 allegedly flipped a coin to decide between two final designs for the reverse of a commemorative silver dollar. The winning design became the medallion that sits in the Smithsonian. The losing design was melted down and its draftsman was paid a kill fee. The coin that decided the coin is itself now in the Mint's archives, an object that once decided its own siblings.
This story is semi-apocryphal but frequently repeated by numismatists. What is verifiable is that the Mint has used coin flips to break design ties in the modern commemorative program at least twice. A coin deciding a coin's fate is a loop that feels like it should trigger some kind of statistical singularity.
8. The Taft-Roosevelt Bull Moose ticket — 1912
At the 1912 Republican National Convention, Theodore Roosevelt and William Howard Taft split the party in what became one of the most consequential primary fights in American history. At several state caucuses — most notably Washington state — contested delegate slots were decided by, literally, coin flips between Roosevelt and Taft supporters. Taft's side won more of the flips, which cemented his nomination.
Roosevelt walked out, founded the Bull Moose Party, split the Republican vote, and handed the 1912 general election to Democrat Woodrow Wilson. Wilson went on to lead America into World War I. If a few coin flips at the Washington caucus had gone the other way, Roosevelt might have won the nomination, kept the GOP united, and the 20th century could look meaningfully different. A few coins flipped in Tacoma rewrote fifty years of American foreign policy.
Bonus: the FLIPSTREAK leaderboard record, right now
This list ends with a small, modern, provably fair coin flip: whoever currently holds the FLIPSTREAK leaderboard record got there not by a single miracle toss but by a sequence of consecutive same-side flips that, probabilistically, would have taken thousands of sessions to stumble into. Every flip in that streak was a single coin's decision. Every one of them could have gone the other way. None of them did.
That is what a record streak is — a small stack of independent coin flips that decided, against all odds, to agree.
If you want to see how your flips compare, every single toss on FLIPSTREAK is logged, ranked, and attributable. A provably fair system makes sure the coins themselves cannot lie. All that is left is to flip enough of them.
