By the end of 2012, the two parties appear to have settled their case out of court, with Rothstein's appeal dismissed and the airline's counterclaims dismissed with prejudice. Litigation was delayed due to the airline's filing for Chapter 11bankruptcy.
Rothstein sued American Airlines in the United States District Court for the Northern District of Illinois, arguing that 'American waived its rights to enforce the contract by not cracking down on Rothstein sooner' according to District Court Judge Virginia Mary Kendall who denied Rothstein's motion in 2011. A letter from the airline was hand-delivered to him at the airport informing him that the pass had been terminated due to fraudulent behavior, specifically his history of approaching passengers at the gate and offering them travel on his companion seat and for using the companion program to purchase an adjacent empty seat under a fake name to keep them vacant, which was often used for privacy or extra carry-on luggage. On December 13, 2008, Rothstein checked in at Chicago O'Hare International Airport with a friend for a flight to Bosnia. Then American Airlines CEO Robert Crandall wrote Rothstein a letter on 13 January 1998 saying 'I am delighted that you’ve enjoyed your AAirpass investment – you can count on us to keep the Company solid, and to honor the deal, far into the future.' During the more than 10 years Rothstein owned the pass, he traveled more than 10 million miles, accumulated over 40 million frequent flier miles (all of which he gave away), made more than 500 trips to England alone and cost the airline more than $21 million according to them. Rothstein negotiated additions to the contract, including a provision for his companion to fly on flights immediately before or after his flight. He added a $150,000 companion pass 2 years later. Steve Rothstein, a financier then from Chicago, upgraded to a lifetime AAirpass for $233,509.93 on October 1, 1987, after a discount of $16,490.07 for the value of mileage on a previous AAirpass.
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