Chalk, (Oscar) Roy

(b. 7 June 1907 in London, England; d. 1 December 1995 in New York City), flamboyant businessman with diverse holdings in transportation, real estate, and publishing.

Chalk was one of three children of a Russian father, Bennett Chalk, and a Polish mother, Sophie Stern Clark. When Chalk was three years old, his family moved to the United States, where they settled in the Bronx, New York. Bennett Chalk was a shopkeeper who moonlighted as a cantor at the synagogue near the family home. The Chalks soon moved to Manhattan’s Upper West Side, where Chalk attended public school and insisted that his friends call him Roy. (Throughout his life, calling him Oscar was an invitation to rebuke). Chalk played stickball with boys from the neighborhood, including George and Ira Gershwin and Lou Gehrig.

Bestowed with a sense of self-sufficiency at an early age, he entered night school at New York University after graduating from the High School of Commerce and worked at odd jobs during the day. He received his law degree in 1931 and was admitted to the New York State bar in 1932. Specializing in real estate transactions and landlord-tenant disputes, Chalk opened an office in midtown Manhattan.

In 24 December 1931, Chalk married Claire Cole; they had one child. His marriage was a key event in his rise up the social ladder. With the financial help of his father-in-law, Herman Cole, a prominent New York real estate investor, Chalk bought a sixteen-story apartment house on Fifth Avenue for one million dollars. The investment proved wise and launched Chalk into construction and real estate. He soon owned an array of valuable properties in Manhattan and the Bronx. The son of an immigrant, Chalk was a millionaire at thirty.

Despite his success, Chalk was constantly striving, reinventing himself. During World War II, he worked with the military, first as a civilian lawyer, then as an aeronautical training consultant. In the latter position he saw an opportunity, and founded a lucrative company, Metal Associates, Inc., to make electronic training devices for the army and navy. When the war ended, Chalk bought two ragged DC-3 airplanes and started Trans Caribbean Airways. He operated nonscheduled flights between New York City and San Juan, Puerto Rico, and was able to offer lower fares and better service than his competitors, Pan American and Eastern. Subsidiary to the airline, he acquired International Railways, a 795-mile railroad line that hauled bananas across Central America. Chalk even owned a banana plantation for a brief time.

When the Korean War broke out in 1950, Chalk saw another opportunity. The army was short of transport planes for cargo and troops, and turned to the nonscheduled airlines’ association, the Air Coach Transport Association (ACTA), which parceled out business to its constituent airlines on an equal basis. Chalk formed a competing association, the Independent Military Air Transport Association (IMATA), allowing his airline, Trans Caribbean, a larger share of business than if it had remained in the ACTA. In this and other exploits, Chalk revealed an ability to cultivate politicians. In 1957 Trans Caribbean Airways was certified by the Civil Aeronautics Board to fly scheduled routes, making it the first nonscheduled airline in two decades to gain certification.

Turning his attention from the air to the ground, Chalk in 1956 bought the broken-down Washington, D.C., Transit System from a private financier, edging out a competitor’s bid by trading on his political connections. He succeeded in lobbying for a fare increase of five cents, exemptions on fuel taxes, and a subsidy for carrying schoolchildren at reduced fares. Chalk repaid the support of his political friends and investors, rejuvenating the company by sprucing up the buses and adding air-conditioned coaches, express routes, and service to the suburbs. Net income nearly doubled, and Chalk paid off a $9 million loan in two years, well before it was due.

In 1962 Chalk entered the publishing world by acquiring the Spanish-language daily newspaper El Diario de Nueva York, with a large circulation among New York’s Puerto Rican population. Soon Chalk set out to undercut the rival newspaper La Prensa by dropping El Diario ’s newsstand price. Within six months, Chalk bought out La Prensa and merged the two papers. The newly merged El Diario—La Prensa became a powerful voice in city and national politics. Although Chalk had been a supporter of Republican President Dwight Eisenhower at the time he bought D.C. Transit, his editorials praised Democrats and blistered Republicans. During the 1960s he became a prominent fund-raiser for the Democratic Party. He also bought an advertising agency, three television stations in Puerto Rico, and a number of radio stations, in addition to his ever-expanding portfolio of real estate holdings.

In the latter part of the 1960s and early 1970s, however, Chalk’s fortunes began to wane. Trans Caribbean Airways was running large deficits and was sold to American Airlines for stock spin-offs and a consulting contract. D.C. Transit also turned unprofitable and lost favor with the public. Chalk himself became a controversial figure in Washington and a lightning rod for public dissatisfaction with privately owned urban transit. Repeated fare increases, coupled with large dividends for shareholders, brought on lawsuits and boycotts (one led by the youthful Marion Barry, later controversial in his own right as Washington’s mayor), prompting calls in Congress that the government take over the system, which it did in 1973.

Chalk sold El Diario—La Prensa to Gannett Company in 1981, but he refused to slow down. He helped found the American-Korean Foundation to foster closer ties between the United States and South Korea, earning the National Medal of Honor from the South Korean government and honorary citizenship. He was also chairman of the American Jewish Committee and the United Nations Finance Committee.

At the age of eighty-three, Chalk’s life seemed to come full circle. He was hired by the Russian president Boris Yeltsin and prime minister Ivan Silaev as a lobbyist and financier to raise money for the Russian Republic while forging ties throughout the United States. The job allowed him to wed his Russian roots, his jet-setting lifestyle, and his ferocious cultivation of the American political and business establishment.

A throwback to the nineteenth-century era of self-made tycoons, Chalk was famed for his large fortune and flamboyant tastes. In addition to a twelve-room apartment on Fifth Avenue in Manhattan, Chalk and his wife owned a thirty-acre estate in Falls Church, Virginia, and a home in Palm Beach, Florida. They traveled frequently to London and Monaco, where he moored his 165-foot yacht, the Blue Horizon. He indulged his fondness for art and fashion, owning paintings by Renoir and expensive suits by the dozen. Chalk died of cancer at New York Hospital. An aggressive businessman, Chalk often acted first and considered the consequences later. “A lack of knowledge is a great advantage,” he once said. “With ignorance, you proceed with confidence where you would otherwise proceed with trepidation.”

The best overview of Chalk’s life is in Current Biography (1971). He was also a frequent subject for reporters and magazine writers and was featured in Coronet (Aug. 1966), Forbes (1 June 1965), New York Herald Tribune (8 Dec. 1962), Newsweek (4 June 1962 and 17 July 1967), Status (Jan.-Feb. 1966), Time (4 May 1970), and, especially, articles in the Washington Post from 1962 to 1991. Obituaries are in the New York Times and Washington Post (both 2 Dec. 1995).

Timothy Kringen