Plains All American lost $162M on a rogue trader who forged the president's signature

Plains All American Pipeline is a midstream energy company that transports and stores crude oil. In the late 1990s, crude oil trader James M. Stewart began making unauthorized short-sell trades — betting that oil prices would fall. When oil prices instead rose sharply from roughly $10 per barrel in late 1998 to over $27 per barrel by November 1999, the company was forced to deliver oil at far below market prices.

Stewart concealed the losses by making false entries in the company's record-keeping system, inaccurately recording purchase prices to hide the growing gap. He also sent letters bearing the forged signature of the company's president to make it appear he was authorized to execute the trades. The unauthorized trading spanned from January 1998 to November 1999, when the company finally discovered the losses.

The $162 million loss was disclosed in late November 1999. Plains All American's shares and partnership units lost roughly half their value. The company defaulted on some debt agreements and faced shareholder lawsuits, though it eventually recovered with new credit agreements. Stewart was indicted on three counts of wire fraud in September 2002 and pleaded guilty in 2003.