What was the biggest contractual loophole in history?

Answer by James Gerber:

I’d say it was in the contract Carl Icahn signed when he sold TWA airlines. He was to receive a 45% discount on all tickets he bought. He then signed an agreement with a discount ticket operation who sold millions of tickets. The new owners tried to get out of the agreement claiming it was only for tickets for Icahn’s personal use. Icahn pointed out at the trial that he rarely (if ever) flew on commercial flights, having his own jet. The courts sided with Icahn and this cost TWA 100’s of millions of $. They couldn’t discount their own tickets because Icahn would qualify for 45% off that lower fare!

What was the biggest contractual loophole in history?

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