The Most Expensive Typos in History

1. MIZUHO SECURITIES SELLS LOW—LIKE, REALLY LOW

The damage: $340 million

In December 2005, Japan’s Mizuho Securities introduced a new member to its portfolio of offerings, a recruitment company called J-Com Co., nicely priced at 610,000 yen per share. Less than a year later, one of the company’s traders made more than a simple boo-boo when he sold 610,000 shares at one yen apiece. No amount of pleading to the Tokyo Stock Exchange could reverse the error.

2. JUAN PABLO DAVILA BUYS HIGH, SELLS LOW

The damage: $175 million

Online trading was still in its relative infancy in 1994, a fact Juan Pablo Davila will never forget. It all started when the former copper trader—who was employed by Chile’s government-owned company Codelco—mistakenly bought stock he was trying to sell. After realizing the error, he went on a bit of a trading rampage—buying and selling enough stock that, by day’s end, he had cost the company/country $175 million. Davila was, of course, fired. And Codelco ended up filing suit against Merrill Lynch, alleging that the brokerage allowed Davila to make unauthorized trades. Merrill coughed up $25 million to settle the dispute—but not before a new word entered the popular lexicon: davilar, a verb used to indicate a screw-up of epic magnitude.

3. NASA’S MISSING HYPHEN

The damage: $80 million

Hyphens don’t usually score high on the list of most important punctuation. But a single dash led to absolute failure for NASA in 1962 in the case of Mariner 1, America’s first interplanetary probe. The mission was simple: get up close and personal with close neighbor Venus. But a single missing hyphen in the coding used to set trajectory and speed caused the craft to explode just minutes after takeoff. 2001: A Space Odyssey novelist Arthur C. Clarke called it “the most expensive hyphen in history.”

4. CAR DEALERSHIP PULLS A MICHAEL SCOTT

The damage: $50 million (or $250,000 in Walmart dollars)

And you thought alien sightings were the only interesting thing happening in Roswell, New Mexico! In 2007, a local car dealership came up with a brilliant plan to stimulate sluggish sales: mail out 50,000 scratch tickets, one of which would reveal a $1000 cash prize. But Atlanta-based Force Events Direct Marketing Company mistakenly upped the ante when they printed said scratch tickets, making every one of them a grand-prize winner, for a grand payout of $50 million. Unable to honor the debt, the dealership instead offered a $5 Walmart gift certificate for every winning ticket.

5. AN EXOTIC VACATION BECOMES X-RATED

The damage: $10 million (plus $230 per month)

Remember the Yellow Pages? Yeah, well Banner Travel Services would like to forget them. Years ago, the now-shuttered Sonoma, California-based travel agency decided to market its services in the phone book ... only to find that the final printing advertised its specialization in exotic destinations as a forte in “erotic” destinations. The typo certainly piqued the interest of some new customers, just not the kind of clientele the company was hoping to attract. The printer offered to waive its $230 monthly listing fee, but Banner sued for $10 million anyway.