I was never quite sure if the AOL/Time Warner merger* or DaimlerBenz's purchase of Chrysler was the Stupidest Business Decision Ever. They bought it for $36 billion in 1998 and are now selling 80% of it for $7.4 billion today, around $5.9 billion in 1998 dollars.
*Stupid for Time Warner, of course, genius for AOL shareholders.
