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.
AOL buys Time Warner for $182 billion, spins off at $36 billion
Overpayment in 2000: $146 billion
Inflation-adjusted: $183 billion
AOL bought Time Warner for $182 billion at the peak of the Dot Com Bubble. Nine years later, Time Warner spun off with a market cap of $36 billion -- a $178 billion loss. The newly separated AOL was valued at only $2.5 billion.