Write-down in 1994: $3.2 billion
Inflation-adjusted: $5.6 billion
In 1989, Sony scooped up Columbia Pictures for $4.8 billion. But the cost of the deal increased when Sony had to spend $200 million to buy another production company and $500 million to settle a lawsuit. All this to produce such movies as Blankman. By 1994 Sony took a $3.2 billion write down on the deal.
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.