He didn't deal with random ticket agents. Lifetime pass holders call a dedicated number just for them. Those answering knew who he was and he knew them by name.

If you have the American Express Black Card, sure. These customers were handled by the standard Executive Platinum team.

Per the article, he very much knew all the personnel by name, to the point of sending them gifts and calling his "friends" to talk about anything and everything when feeling depressed.

Are you sure? I've been AirPass before and we book through different agents. Same when ConciergeKey wasn't a published benefit.

He didn't place his trust in ticket agents (though his were far from random). He had a handwritten letter from CEO Robert Crandall: "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."

The CEO wrote him a letter saying, “Sure, go ahead and book an empty seat for your suitcase under the name Bag Rothstein”? Because if not, it sure sounds like he put his trust in ticket agents.

I mean, I wouldn’t trust a ticket agent to manage my finances, but you kind of have to assume they know how to do the one thing they were hired to.

Just different risk tolerances I guess. If I had spent $500k on something that could be worth $10+ million, I wouldn't take a risk based on the word of a front-desk person.

My belief is that this guy truly knew he was in the wrong and did it anyway because he thought he could get away with it. Classic rich guy move that came back to bite him.

Aside from the booking staff, who could he reasonably have expected to advise him? The only people who could actually say if AA considered this behavior abusive would be members of the airline's legal staff of senior management. Any other attorney or other form of advisor can't possibly definitely state what AA would consider abuse.

These aren't random front-desk booking agents, they're high up enough in the chain of command to deal with customers like the unlimited pass holders. Who else could he have trusted to tell him if the behavior would constitute fraud in America's opinion?

Well the people so far up in the chain of command clearly advised him incorrectly so that argument doesn’t hold water.

Again, if I’m risking $5+ million I FIND SOMEONE TO ADVISE ME. Dude’s a Bear Stearns trader with money to burn, you’re telling me he has no way to get ahold of the airline’s legal staff or senior management?

And also again, the reason this guy took their word for it is that he knew he was angle-shooting and thought it wouldn’t come back to bite him.

The legal requirements for a party to make an adverse decision is low, it just has to be non-arbitrary to prevent it from being judged on the merits. At which point whichever party has the greater resources would be most likely to win.

When dealing with a corporation, you are at their mercy, and the most immediate defense is whatever PR problems you can cause them.

Of course, that was during a time when a promise like that still meant something. And by the time they decided to renege he was long gone.