Worst Mistakes In History, Mercedez-Benz buys Chrysler
Overpayment in 1998: $20 billion
Inflation-adjusted: $26.6 billion
In 1998, Mercedes-Benz merged with Chrysler to create Daimler Chrysler, for $37 billion. But the merger didn’t work out as planned and by 2007, Mercedes sold Chrysler Cerberus Capital Management for only $7 billion.