$225,000,000 gone with one typo

Back in 2005, a Japanese trader tried to sell 1 share of a company for 610,000 yen
He accidentally typed it as 610,000 shares for 1 yen each
Tokyo Stock Exchange's system didn't catch the error and his firm lost roughly $225 million in minutes
They tried to cancel but it was already too late
It caused so much damage that the president of the Tokyo Stock Exchange later resigned
The most expensive typo in the history of finance