The story is sordid and long, but the details were made clear by Matt Viser’s excellent Globe piece. To wit: Lorenzo sold the Donald the Eastern Shuttle for an overvalued $365 million (if DT had created a brand-new shuttle from the ground up with brand-new planes, not old worn-out 727s, estimates were that he could have done it for $300 million.) Of course, the money was all borrowed. It was 1989; Eastern (and Continental) were already almost dead from Lorenzo’s sledgehammer and the economy was tanking. Pan Am 103 was bombed, the first Gulf War was about to begin. It was incredibly bad judgement to overpay a bunch of other peoples’ money for something that was guaranteed to tank.