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Charlie's death has been called the "defining crisis" in Dean's life, the impulse that focused him. But it's a little more complicated. Even before his brother's death, Dean had sought a world beyond the moneyed Atlantic coastline. As a senior at St. George's, Dean requested that Yale--where he enrolled in 1967, when Bush was beginning his senior year--pair him with black roommates to give him another view of the world. He got two African-American roommates and one from rural Pennsylvania. "I had known people of different kinds before," Dean says, "but I had never lived with people that were so different, and it was wonderful."
Though he says he "didn't do much protesting," Dean opposed the Vietnam War. So it was fortunate that officials at the U.S. Army garrison at Fort Hamilton in Brooklyn gave him a deferment because of a minor back problem. Dean has an unfused vertebra that keeps him from running long distances and occasionally leads to discomfort. But after graduating from Yale in 1971, Dean--who didn't want to follow his friends to law school--spent a year skiing and bumming around Aspen, Colo. He hit the slopes, tried pot, washed dishes, poured concrete and drank impressive amounts of beer.
Being a burnout got old after a year, and Dean decided his life could take one of three paths. He could teach, as he had done for three months at a junior high school in inner-city New Haven, Conn., near Yale. He could be a doctor. Or he could take "the path of least resistance" and go to Wall Street. He quickly dismissed teaching as "too hard ... There were a lot of kids with enormous numbers of needs, and I couldn't meet them all." Medical school would require enrolling in difficult premed classes, since he had done little science at Yale. So he became a stockbroker.
"He liked Wall Street," says Andree Dean, "but he wasn't doing anything to help people." Howard had "always had a feeling for--I don't want to say the underdog, but he's always wanted to help people." Still, she was surprised to run into her son one day at Columbia, where she was getting her art degree. "He was secretly going to premed classes without telling us," she says, with a reminiscent smile. Dean was nervous when his parents found out. He describes his father as "a strict disciplinarian," and he was sure the old man would think leaving finance for medical school "was crazy. But he never said one word about it. I would have done it anyway, but it just would have been harder ... In some ways that was the best thing he ever did."
From then on, his life took a different path from what one might expect of a Dean or a Maitland. He chose Albert Einstein College of Medicine in the Bronx, a school known for its hands-on, community-based approach to teaching medicine. It was at Einstein that Dean met Judith Steinberg, a studious Princeton grad from Roslyn, N.Y., a precinct of Long Island somewhat less tony than the ones Dean knew well. After a long courtship, he and Steinberg were married by a judge at the Fifth Avenue Hotel in Manhattan on a winter night in 1981.