1999 Oldsmobile Alero
In 2000, chief executive officer Rick Wagoner decides to kill GM's Oldsmobile brand. The brand has been sinking for years, especially after the company tried to shift marketing strategies towards a younger demographic. The phase-out ends up costing GM over $1 billion.
NEXT: Kerkorian buys in
Last updated November 25 2008: 7:53 AM ET