O. Roy Chalk

Oscar Roy Chalk (June 7, 1907 – December 1, 1995) was a New York entrepreneur who owned real estate, airlines, bus companies, newspapers and a rail line that hauled bananas in Central America. His diverse holdings included DC Transit, Trans Caribbean Airways, the Houdon bust of Thomas Jefferson now at Monticello, the Chalk Emerald, and the New York Spanish-language newspapers El Diario de Nueva York and La Prensa, merging them into El Diario La Prensa.

Chalk was born in London, England and emigrated to the United States at age three. He grew up in the Bronx, where his neighbors included Ira and George Gershwin and Lou Gehrig.

He graduated from New York University and its law school. He learned the real estate business and bought several apartment buildings.

He started Trans Caribbean Airways in 1945 for $60,000, with two DC-4s. It was through the airline that in the mid-1960s he eventually purchased the 800-mile rail line, International Railways of Central America, that transported bananas in Central America. He later purchased a banana plantation, which he owned for a time. Chalk sold his airline to American Airlines on March 3, 1971, in exchange for stock and became the single largest shareholder.

He purchased the Washington, D.C. transit system on August 15, 1956, for $13.5 million, renaming it DC Transit, and in 1959 attempted to purchase New York City's transit system, but city officials rejected the offer after weeks of serious consideration.

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