102. The Reply-All Blunder by The New York Times
Year: 2011
Location: New York, New York
Company: The New York Times Company
Estimated Damage Value: Unknown
In 2011, The New York Times made a classic mistake by sending a ‘reply all’ email meant for a few hundred past subscribers to a vast audience. This mishap, occurring in the mass media giant’s New York headquarters, remains a memorable faux pas without a clear cost to the company’s finances.

Attempting to win back subscribers with a 50% discount, the email erroneously reached 8.6 million people, far beyond the intended few hundred. The New York Times’ initial denial of sending the email compounded the error, impacting their reputation more than their finances.