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A Boy and His Airline

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“Let’s do a Dr. Ruth spoof,” says Herb Kelleher, jumping to his feet in a spasm of creativity. Kelleher is brainstorming with three of his top managers in his cluttered Southwest Airlines office near Dallas’ Love Field. The task at hand is to come up with skit ideas for an airline-industry conference. Kelleher envisions a scene in which Dr. Ruth would be on the telephone talking to Robert Crandall, the abrasive head of Dallas-based American Airlines, which has just become the largest domestic carrier. “Remember. Bob,” Kelleher says, mimicking the tiny sex doctor, “size isn’t everything.”The focus shifts to New York deal-maker Donald Trump and his attempt to purchase the Eastern Airlines Shuttle, which runs between Boston, New York, and Washington. Someone suggests a musical…

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