Last September, at a debate sponsored by the Congressional Black Caucus, Howard Dean declared, "I'm the only white politician that ever talks about race in front of white audiences." The other candidates were dumbfounded by Dean's assertion and quickly denounced him, citing their own various commitments to civil rights. Dean's blurt was unsupported, although not uncharacteristic. Voters could only wonder: what made Dean, the governor of a small, virtually white state, think he was the only politician brave enough or sensitive enough to talk openly about race?

Dean likes to say that he doesn't just pop off, that he often turns over a problem in his head for days, though he admits that sometimes the nuances get lost when he finally expresses himself. That may describe the mechanics of Dean's thinking, but it doesn't reveal much about his inner convictions. Dean has awkwardly described his courtship of his wife, Judy, to People magazine and acknowledged that he is a cheapskate and a bit of an insomniac. Voters can only wonder: what makes Dean--an upper-crust kid who, win or lose, has emerged as a great liberal icon--Dean?

He's not the one to ask. "Never complain, never explain" is an old WASP expression. Coined by the 19th-century British statesman Benjamin Disraeli as a way of justifying the empire, it has been adopted by the likes of Katharine Hepburn, Henry Ford II, George Bush (the father) and the Central Intelligence Agency. It might as well be Howard Dean's mantra. Most candidates weave their personal stories into their stump speeches (John Kerry the war hero, John Edwards the mill-worker's son). Dean rarely talks about his shaping experiences or social background. His wife never campaigns with him, and the couple seldom socialized with others at home in Vermont. Dean comes across as a bit of a self-righteous loner.

Dean's impetuosity, his willingness to say what's on his mind--whatever is on his mind--is a refreshing contrast to the typical calculating, slick politician. But he can also seem overbearing and recklessly shoot from the hip. This week in Iowa and next week in New Hampshire, voters will have to decide whether Dean is reassuringly confident--or unnervingly cocky. Dean himself is not likely to engage in meaningful self-analysis (he declined to be interviewed for this article). He does not like to talk about his coming of age at a posh New England prep school. But that is a good place to begin to understand him.

He was born into what the late columnist Joe Alsop called "the WASP ascendancy," just before that tight, in-grown world began to unravel and decline. Dean grew up with the trappings of old money--the Park Avenue apartment, the weekend house in East Hampton--but also the caution that wealth and social position should not be flaunted. The arbiters of the old East Coast establishment were sensitive to charges of snobbery. At the same time, Dean, like any prep-school boy of his time, would have had a pretty clear sense of where he belonged in the wider world: on top.

Dean's father, "Big Howard" (who, like "Little Howard," was short), was a backslapping hail-fellow-well-met. He was a diehard Republican who railed against subversives and made casual racist and anti-Semitic remarks, though apparently without conscious malice, or at least much self-awareness. "Dad was a major-league conformist who believed in the path to success," recalls Dean's younger brother Jim. The path ran through Yale (though Big Howard flunked out after two freshman years), Wall Street (where Big Howard sold stocks and bonds) and the Maidstone Club (the Hamptons' most exclusive; at the time, no blacks, no Jews).

The dinner table, with four boys and a loud, opinionated father, was "raucous," says Jim Dean. "It was 'Speak now and don't hold back'." The boy who most enjoyed jousting with Big Howard (and the most like him) was Charlie, the Deans' second son, a mischief maker and a wiseacre. By comparison, Little Howard, the eldest boy, "was a shrinking violet," says brother Jim. The boys' mother, Andree, was very straightforward, like the rest of the family, but she had a light, disarming touch. Without being confrontational, she went her own way. When Howard senior visited the boys' boarding school, St. George's, in Newport, R.I., Andree, a Roman Catholic, would not accompany her husband to chapel. Rather, recalls the school's former chaplain the Rev. Hays Rockwell, she would sit outside, reading The New York Times. "She was lovely and unaffected," recalls Rockwell. "The younger masters [teachers] called her a 'yummy mummy'." She was also an example of quiet independence to her son.

With its Gothic chapel and red brick dormitories, St. George's sits high atop a hill overlooking the water near one of the nation's most exclusive summer enclaves. The school exudes privilege, if a bit grimly when the winter wind blows. "High above the crashing breakers / Testing ground for victory makers" goes a school song. The parents of St. George's boys were mostly moneyed Republicans. But the faculties of New England church schools were often more liberal, especially so at St. George's when Howard enrolled in 1962.

The headmaster, Archer Harman, was so committed to civil rights that he marched, defying police dogs and singing "We Shall Overcome," to register black voters in Selma, Ala., in 1965. When Harman moved to integrate St. George's with its first black students at about this time, he was almost fired by the school's conservative trustees. The school's most popular and dynamic young teachers, the co-chaplains Rockwell and Robert Gregg, along with the football coach, Chris Corkery, threatened to quit if the trustees didn't back down. (The trustees did, though the first black student was a tragic case. A great football player and teammate, though not close friend, of Howard Dean's, Conrad Young ran away from school after two years and later hanged himself.)

The so-called St. Grottlesex schools (Groton, St. Paul's, St. Mark's, St. George's and Middlesex) were regarded as playgrounds of the spoiled rich. But, in part to rebut the stereotype, they attempted to be moral incubators, preaching "muscular Christianity" and the duty to serve "in the larger light of the world." Chapel was seven days a week and twice on Sunday.

Every Thursday evening at St. George's, Headmaster Harman would take to the pulpit and "remind the boys of their responsibilities," as Harman recalled in an interview with NEWSWEEK (Harman, 80, had just come in from skiing in 10-degree weather). The boys were told to shed their conformist cynicism, to fight the good fight, wherever evil lurked. "Soon you shall be forced to take sides, by doubting or scoffing or hiding in the crowd, hoping not to be noticed; or by standing up and declaring yourselves," reads the school's 1965 Prize Day sermon. "Beware of the subtleties and the undramatic. Selma is easy and so is the Peace Corps"--easy, presumably, in the sense that even the densest schoolboy could see that standing for civil rights and helping the world's poor are the right thing to do. "But there are also," the sermon warned, "fraternities that so quietly take no Jews... "

Many boys snickered or yawned at the do-good exhortations and became investment bankers or lived off their trust funds. Sarcasm was the lingua franca of prep-school boys in that era. The cooler ones affected a kind of worldly cynicism and sneered at excessive sincerity (picture George W. Bush cutting up as an Andover cheerleader). Dean, in contrast, was unapologetically earnest--a "straight arrow verging on goody-two-shoes," according to his classmate Jim Torrey. He was teased mercilessly for keeping barbells in his dorm room so he could lift weights (this was an age when it was considered in to sneak cigarettes, not pump iron). Dean was not much of a quipster. "He didn't suffer fools," says his football coach Chris Corkery. "He was short with people."

Still, he was respected. He was one of five elected senior prefects, charged with looking after the younger boys. "His authority did not depend on bullying," recalls his housemaster, Rockwell. "He appealed to the decency of ninth graders, whatever there was of it." Dean's wrestling coach as well as his housemaster, Rockwell watched admiringly as he relentlessly did bridging exercises to strengthen his neck. The solitariness of single combat appealed to Dean, says Rockwell: "I think he liked it out there alone, where you can't blame anyone else."

For a supposed sanctuary, St. George's was remarkably attuned to the world's woes. The school canceled classes for a day in the spring of 1965 to discuss the Vietnam War. Coach Corkery, who taught Asian history to Dean, recalls concentrating on the evils of colonialism and how the French had come to grief in Southeast Asia. The prep-school students turned against the war while many college campuses were still asleep. When a Marine colonel came to speak at the St. George's chapel, some seniors hung out the Viet Cong flag.

In the fall of '65, Dean and some other senior boys were allowed to skip their required "sacred studies" course and instead take an ethics-and-philosophy course taught by Rockwell. "We talked about the civil-rights movement all the time," says Rockwell. (Last month, when Dean mistakenly placed the Book of Job in the New Testament, Rockwell and his former co-chaplain Bob Gregg jokingly argued over which one of them was to blame.)

Many students of the era rebelled when they went off to college. They grew their hair and fought with their parents. Dean went to Yale with his social conscience fully formed. One of his close friends at Yale, David Berg, says he was "stunned" to learn, years later, that Dean had requested to room with minority students. "I was a Jewish kid from public school, just glad to get into Yale. But when he got in, it was 'OK, Yale, here's what I want from you'."

One of Dean's black roommates, Ralph Dawson, was surprised to find that Dean, unlike many other Yale kids, downplayed his wealth. Was Dean self-conscious among blacks? "As white folks go?" replies Dawson. "Not at all." Dean liked to argue--"he was combative," Dawson recalls. Dawson was also struck by Dean's frugality; ordering pizza, he always wanted to save money by skipping the extra topping. When Dean tutored black kids in New Haven, the students took pity on his drab, shabby clothes and took up a collection to buy their teacher an electric blue and orange striped shirt, a pair of pants and some shoes. (Dean comes by his flinty New England cheapness naturally: his mother disliked paying for taxis in New York City; when she was in her 60s, she grew tired of taking the bus downtown and learned how to in-line skate instead.)

Dean was not a student radical, and though he joked about his father's conservatism, he never seemed angry about it. Dean's liberalism had been sanctioned, if not inspired, by his prep-school headmaster; he loved his father; who was he to rebel against? He joined a preppy fraternity, but--mindful of that Prize Day sermon about quiet wickedness--he quit when the frat refused to open up to Jews and blacks. Dean continued to stand up against the bully. In a touch-football game, a big kid with an ROTC scholarship roughed up the young son of Yale's antiwar chaplain, William Sloane Coffin. Dean jumped in: "How dare you!" and accused the ROTC student of political motives.

Able to avoid the draft with a bad back, Dean drifted for a time after college and felt guilty about it. After getting booted from Yale on the eve of World War II, Big Howard had been unable to join the military because of complications from a childhood illness. But the senior Howard had not stayed home: he had obtained a civilian job handling war logistics in Africa, India and Asia. Little Howard, by contrast, wandered off to Aspen, Colo., to be a ski bum. Then there was the example of his younger brother Charlie, who worked with poor kids in the inner city and in 1972 headed off to Southeast Asia with a backpack.

Charlie disappeared. It would be nearly three decades before his remains were recovered in a rice field; he was presumed to be a victim of Laotian communists fighting in the still-sputtering war. The close Dean family was shattered. Big Howard could not talk at all about Charlie's death. Little Howard was stricken. At St. George's, Charlie had been elected head boy. He had been the popular one, the true politician in the family. Dean had even talked of working as Charlie's campaign manager one day.

Dean's commitment to public service was "sharpened" by Charlie's death, according to his uncle Dr. William Felch, who encouraged him to go to medical school. Dean himself spoke cryptically and enigmatically about the impact of his brother's death in an interview with The New Yorker magazine. "Experiences that I don't have access to consciously are what drive me--personal experiences that I can't tell you about because I haven't processed them," Dean told the New Yorker writer, Mark Singer. "What experiences might those be?" Singer asked. "Aspects of my brother getting killed," replied Dean. "Aspects of, who knows, whatever went on in my childhood. That sort of thing."

After suffering anxiety attacks as a doctor in the mid-'80s, Dean briefly underwent psychotherapy ("I never missed a day of work," he told NEWSWEEK) and now talks somewhat vaguely about his "survivor's guilt" over Charlie's death. But Dean does not appear to have delved too deeply into his psyche. Unlike most schoolboys, he never really doubted who he was, according to his old St. George's chaplain, Rockwell. "There was a wholeness about him. He was not fragmented," says Rockwell. By the time Dean graduated at 17 in 1966, he was "one," says Rockwell, forged by family, his class, his school and the tumultuous time when he came of age.

Editor's Picks

Newsweek cover
  • Newsweek magazine delivered to your door
  • Unlimited access to
  • Ad free experience
  • iOS and Android app access
  • All newsletters + podcasts
Newsweek cover
  • Unlimited access to
  • Ad free experience
  • iOS and Android app access
  • All newsletters + podcasts