It appears that TWA owed him money so he negotiated the cheap ticket as a form of payment...[1] How convenient that Marc left that out of his blog post...
In the interim, Icahn negotiated for airline vouchers from the company in lieu of the $190 million that TWA owed him. As the deal included the provision that he could not sell these tickets through travel agents, Icahn founded LowestFare.com, where he both sold the tickets and created a revolution in the travel industry.
[1]http://www.investopedia.com/articles/financial-theory/08/car...
One of those creditors, to the tune of $190 million, was Icahn. He resigned as chairman in 1993, and by 1995 he was growing impatient to be repaid. TWA executives, desperate to bring the tragic Icahn chapter to a close, gave away the farm, the cows and the farmer’s wife. They came up with a deal called the Karabu ticket agreement, an eight-year arrangement that allowed Icahn to buy any ticket that connected through St. Louis… for 55 cents on the dollar and resell them at a discount.
Then of course, if you believe that the company is undervalued and can grow (and that is why you would buy it, anyway), you wouldn't try to force them to pay your money back, because they could generate a positive return on the money.
It's possible that TWA couldn't have been turned around and selling it off was really the best return he could get on his investment -- but I think it's at least debatable whether Icahn did anyone else much of a service. The other shareholders got to exit a company they'd lost faith in and hopefully made some money in the process, but that seems to be it as far as silver linings go.
