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Trans Caribbean, picked up by Chalk 17 years ago for a paltry $60,000, is a similar success story. The line lured many Puerto Rico passengers away from bigger Eastern and Pan American by combining lower fares with free box lunches on economy runs and by putting on in-flight entertainment. The first U.S. charter airline since World War II to be certified by the Civil Aeronautics Board for scheduled flights, Trans Caribbean last week won a three-year MATS contract to fly service families to Europe. To handle the $3,500,000 worth of business that it is guaranteed each year of the MATS contract, Trans Caribbean will have to add more jets to its present fleet of three DC-8s. This will oblige Chalk to negotiate yet another seven-figure loan, but since he has been careful to pay back past loans ahead of schedule, he now has an open-pocketed friend at New York's Chase Manhattan Bank.
That Old Look. Once his new publishing chain shakes down, Roy Chalk will almost surely want more money. His philosophy is to keep what he buys and look around for more. Just where he will turn next he will not confide, but does admit to a continuing interest in the still struggling New York City transit system. Says he with that pocketa-pocketa look in his eyes: "I'm a patient man, and I'm interested."