When Eastern Air Lines started to come apart at the seams, it first tried to save itself from impending collapse. One move was to sell its Eastern Air Lines Shuttle services that operated between New York, Boston, and Washington D.C. to a very familiar name, Donald Trump. The-then 38-year-old service was a cash cow for Eastern. But the Trump Shuttle could not replicate its success and was sold on to USAir in just three years’ time.

In October 1988, Frank Lorenzo, the then-chairman of Texas Air, the parent company of Eastern Air Lines, shook hands with Donald Trump to handover Eastern Air Lines shuttle services between three of the biggest cities on the U.S. Northeast Coast for $365 million. The deal included everything that an airline would need, including 17 Boeing 727 aircraft, equipment and employees. The service, which was once a monopoly, now had to compete with Pan Am’s own shuttle service between the three cities on the East Coast.

The deal almost fell through in 1989, when Eastern’s mechanics went on strike in March 1989. Trump haggled to bump down the original acquisition price of $365 million, as the union’s strike, supported by the carrier’s pilots and flight attendants, eroded its value, argued the then-real estate magnate. The unions were against the deal, as it would push the airline into bankruptcy – its shuttle services were the only remaining profitable operation in Eastern Air Lines, argued the collective. A judge ruled that the workers’ concerns were “overdrawn and inconclusive,“ reported Bloomberg at the time. In addition, Trump himself guaranteed employment to former Eastern employees, including the fact that he would recognize existing labor agreements and the airline’s unions.

Troubling start

To sweeten and conclude the deal, Eastern added four extra 727s, concluding the negotiations in April 1989. On June 9, 1989, Trump Shuttle was ready to depart from New York LaGuardia Airport (LGA) in a terminal, surrounded by “tuxedos and curiosity,” read headlines. The strikes forced Trump Shuttle to retreat and attempt a steep climb up the hill, as Pan Am’s market share on the corridor only grew. Following the temporary stoppage under Eastern Air Lines colors, Trump’s newest venture owned 26% of the market, a deep drop from the previous share of more than 50%, reported The New York Times.

Trump Shuttle Boston to New York flight ticket 
 Trump Shuttle Boston to New York flight ticket case 
 

Trump Shuttle Boston-New York flight tickets. Source: AIR TICKETS HISTORY

The troubling start would hinder Trump Shuttle’s attempt to gain momentum and out-run its opposition. The all-Boeing 727 airline would fail to clear hurdles, including the fact that one of its aircraft would be involved in an incident two months after it started operations. A Trump Shuttle 727 was forced to make an emergency landing in Boston Logan International Airport (BOS) after a front landing gear failure made for a sparkling landing. To avoid any long-lasting backlash, Trump himself boarded a shuttle flight from New York to Boston the next day.