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In October 1988, Donald Trump threw his wallet into the airline business by purchasing Eastern Air Shuttle, a service that for 27 years had run hourly flights between Boston, New York City and Washington, D. For roughly $365 million, Trump got a fleet of 17 Boeing 727s, landing facilities in each of the three cities and the right to paint his name on an airplane.

Trump pushed to give the airline the Trump touch, making the previously no-muss, no-fuss shuttle service into a luxury experience.

To this end, he added maple-wood veneer to the floors, chrome seat-belt latches and gold-colored bathroom fixtures. A lack of increased interest from customers (who favored the airline for its convenience not its fancy new look) combined with high pre–Gulf War fuel prices meant the shuttle never turned a profit.

The high debt forced Trump to default on his loans, and ownership of the company was turned over to creditors.

The Trump Shuttle ceased to exist in 1992 when it was merged into a new corporation, Shuttle Inc.

In April 2006, Trump announced that, after years in the real estate business, he was launching a mortgage company.

He held a glitzy press conference at which his son Donald Jr.

Predicted that Trump Mortgage would soon be the nation’s No. Trump told CNBC, “Who knows more about financing than me? Within a year and a half, Trump Mortgage had closed shop.

The would-be lending powerhouse was done in by timing (the housing market cratered in 2007) and ironically enough, given Trump’s Apprentice TV show, poor hiring.

The executive Trump selected to run his loan company, E. Ridings, claimed to have been a top executive at a prestigious investment bank.

In reality, Ridings’ highest role on Wall Street was as a registered broker, a position he held for a mere six days.

In 1989, the Donald teamed up with Milton Bradley to release Trump: The Game, a Monopolyesque board game in which three to four players must buy and sell real estate and try to trump one another in business deals. filed for Chapter 11 bankruptcy protection for the third time in a row — an extremely rare feat in American business.