[84][85] In 1989 and 1990, Trump lent his name to the Tour de Trump cycling stage race, which was an attempt to create an American equivalent of European races such as the Tour de France or the Giro d'Italia.[86]
From 1986 to 1988, Trump purchased significant blocks of shares in various public companies while suggesting that he intended to take over the company and then sold his shares for a profit,[45] leading some observers to think he was engaged in greenmail.[87] The New York Times found that Trump initially made millions of dollars in such stock transactions, but later "lost most, if not all, of those gains after investors stopped taking his takeover talk seriously".[45]
In 1988, Trump purchased the Eastern Air Lines Shuttle, with 21 planes and landing rights in New York City, Boston, and Washington, D.C. He financed the purchase with $380 million (equivalent to $871 million in 2021)[33] from 22 banks, rebranded the operation the Trump Shuttle, and operated it until 1992. Trump failed to earn a profit with the airline and sold it to USAir.