Word: chalkings
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Dates: during 1950-1959
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Three years ago Chalk bought Washington's well-hated, strike-bound transit system from Louis Wolfson, who had milked it of millions. Chalk put up only $500,000 of his own money, borrowed $9,100,000, plus a $3,900,000 mortgage, to take over a company with a book value of $27 million. He started out by painting Washington's buses glaring green and coral, installed shapely stewardesses on streetcars, last summer rolled out 100 new buses (67 of them air-conditioned) in a downtown parade with four bands, bathing beauties, clowns, calypso dancers. Hoopla-and hustling...
Fair Fare? Chalk pocketed enough in these deals to live in splendor. His twelve-room Fifth Avenue apartment is rich with a Rouault, a Dufy, two Renoirs, two Vlamincks; his Washington office is studded with hi-fi and Queen Anne furniture. Chalk commutes between the two places in his telephone-equipped cars (black Cadillac, white Continental), on off hours retires to his 83-ft., twin-diesel yacht. A careful dresser, he owns 70 suits (most made in Europe for upwards of $200 each) and 30 pairs of shoes (most made in Paris for $75 a pair), sports vests with lapels...
...this year. Last week a private operator offered to relieve New York of this financial headache, reportedly was ready to pay upwards of $500 million in cash and bonds-give or take a few million-for the $2.1 billion transit system. Said O.(for Oscar) Roy Chalk, 51, able admiral of D.C. Transit System, the national capital's surface lines: "I'd like to prove that private enterprise, with $1, can go 50 times the distance that public enterprise...
...Chalk should know. He has run up a $10 million-plus fortune by making every dollar turn over many times-through borrowing. Son of a Russian immigrant shopkeeper, Chalk grew up in The Bronx (his neighbors were George and Ira Gershwin, and he fielded sandlot grounders batted by Lou Gehrig), rode the subways to New York University Law School ('31). With loans and his skimpy earnings as a young attorney, he bought Bronx apartments at Depression prices, later cashed in on World War II's real estate boom. Typical Chalk deal: in 1942 he bought the 16-story...
Hoopla Pays. In 1945, with only $60,000, Chalk founded the nonsked Trans Caribbean Airways by buying two DC-3s, and within two years it was earning $60,000 annually. Trans Carib expanded to lift thousands of refugees from Europe to Israel, tons of airmail from Europe to South America, flew charter trips from Johannesburg to Jerusalem. It grew so strong that in 1957 it won a regular U.S.-Puerto Rico route, became the first nonsked passenger airline in 20 years to win scheduled status (TIME, Dec. 2, 1957). Last year Trans Carib (including its major subsidiary, D.C. Transit) earned...