Sale price: $40 billion
Word association: Mercedes. If your answer wasn't "Chrysler" you may understand why the 1998 move by Daimler ( DAI) to acquire Chrysler was so ill-fated. The $40 billion purchase was positioned as some sort of brilliant takeover of the U.S. auto industry. Combining the pedigree of Mercedes with the mom and pop appeal of Chrysler would lead to the sort of manufacturing efficiencies that would be needed to topple GM ( GM), Ford ( F), Toyota ( TM) and Volkswagen. Not quite. After bleeding money for nearly a decade, Daimler unloaded its slightly used car company to Cerberus Capital Management for just $6 billion. We assume whoever brokered the deal had to consult with a "manager" in the back room before agreeing to the price. No word on whether floormats were included with the deal.