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Born to privilege, searching for a purpose

This is the second in a series of profiles of leading candidates in the 2004 presidential race.

In the winter of 1974, Howard Brush Dean III departed his family's Park Avenue home and boarded a subway for a gritty stretch of the Bronx. Three years out of college, Dean was seeking purpose, after a year skiing in Aspen and two halfhearted years trying to follow his father's footsteps on Wall Street. At 26, he had a trust fund but few accomplishments.

Dean was on his way to Albert Einstein College of Medicine, an institution founded by Jews who had been kept out of other schools.

Dean had never come against such limits: His acceptance into an elite prep school and Yale University had been a family rite; the applications were more a formality than a test. But from his college days when he shared a dorm room with two African-American roommates, he'd pushed against the confines of his exclusive upbringing, embracing the roommates in his world of privilege.

Now, it was Dean seeking entry to an institution created for people forced to stand on the outside.

Crossing the campus of beige, low-slung buildings, Dean arrived at an office occupied by a middle-aged black man, a professor who served as the college's gatekeeper, separating the promising from the pretenders.

``Grades too miserable to discuss,'' the professor wrote on a pad in front of him, using Dean's own words.

But then, the professor noted, Dean spoke with the voice of ``a man twice his age.''

Dean explained that he had fought with his conservative father, enduring his criticism for wearing his hair long and other small rebellions; that he had wanted to leave Yale in his freshman year because he felt directionless, but that he remained to please his father; that he had found a calling while volunteering in a Manhattan emergency room; that there he had discovered a mission to help people.

``He convinced me of an affinity for the sick, seldom seen with much frequency anymore,'' the interviewer, Russell Anderson, wrote in the admissions report. Dean spoke with a frankness, a directness, that left no doubt.

``Howard B. Dean no longer represents a lost soul but you can count him as a winner for he has indeed come home.''

The street not taken

What Anderson saw in Dean that day, it turned out, was not a lifelong commitment to medicine. Rather, he saw a man intent on embarking on a life beyond Park Avenue, beyond East Hampton - one altogether different from the generations of Deans before him, one that ultimately would catapult Dean to seek the presidency of the United States.

In the Dean family, there was a preordained path for its men, marching from Yale to Wall Street. Dean's grandfather had followed it, his father had as well. Dean would trundle down it for a time, to his father's unspoken delight, but he didn't like the work. He may have been of the upper class, but he wasn't going to be hostage to it.

Yet extracting himself from New York society would require time and focus. When he made the break, starting that winter day in the Bronx, it was with a boldness, a brashness, and a headstrong insistence that Anderson, the Einstein professor, deemed a mark of maturity.

Later, others would label it an overabundance of confidence.

``Howard is a very solid resident, a good teacher, intellectual in his approach,'' a senior doctor wrote in a 1977 evaluation of Dean's residency at the University of Vermont Medical Center. ``His major problem continues to be one of impulsive syntheses when problems are approached - he should take care to be more deliberate in making assessments and deciding upon plans. Because of this trait, he is not quite the superior physician that he is in other respects.''

In Vermont, where Dean practiced medicine from 1981 to 1991, he would define himself against expectations: as a doctor who eschewed fancy specialties to work in family practice, as a New York transplant who found a home in Burlington's blue-collar Democratic Party rather than the burgeoning progressive movement, as a Vermont politician who was neither a Yankee Republican nor a Birkenstock-shod activist.

As governor of Vermont for five terms, Dean angered the left by seeking the counsel of a group of conservative businessmen, and he angered the right with staunch support for abortion rights and conservation. Dean was capable of both contrariness and courage, state officials recall, each trait drawn from the same basic quality of deciding what he wanted to do and pushing it through with finger-wagging confidence.

When Dean saw a billboard he didn't like and demanded that it be taken down, aides groaned even as they rushed to obey his command. When in 2000 Dean signed the first law in the country creating civil unions for gays and lesbians, aides marveled at his ability to endure withering criticism for the move and to confront a fierce electoral challenge from the right that nearly cost him the governorship.

Those who know Dean aren't surprised that he has latched onto President Bush like a bulldog: Dean's certitude - which friends insist is more a product of personality than ideology - matches Bush's own single-mindedness. Both speak with the assuredness of the well-born; both cast themselves against type, Bush as the compassionate conservative, Dean as the tightfisted liberal.

Now, with his relentless assaults on Bush, Dean has vaulted to the forefront of the presidential race. Aides promise that voters will see he is more than an attack dog as he emphasizes his mainstream credentials and his front-line expertise in health care. And as he circles back to win over the world beyond Vermont - fund-raising in East Hampton and Manhattan, currying favor with the political establishment - Dean is facing an unusual series of homecomings.

A father's long shadow

The Dean family tree has branches in almost all the elite drawing rooms of Long Island: The Fahys, The Cooks, The Hunttings. George W. Bush's grandmother was a bridesmaid at Dean's grandmother's wedding, according to Robert Dean Felch, Dean's cousin and a family historian.

Dean's family has roots in New York dating to the 1600s. Many of his ancestors settled in Sag Harbor, the seaside town on Long Island, where they worked in the whaling industry and, with its decline, turned to manufacturing watchcases. Their red-brick factory, later bought by Bulova Watch Co., still stands, as does an elegant ancestral home that is now The Whaling Museum.

In the late 19th century, the Deans set their sights on Wall Street, beginning with Dean's great-great grandfather, a sugar broker who lived in lower Manhattan - the first of four generations of Dean men to amass wealth in the financial district.

Dean grew up in a household dominated by the demands of his father's Wall Street job, which often kept the elder Dean working late into the night. Home for the Deans was an 11th-floor Park Avenue apartment, where Howard and his three younger brothers were a rambunctious lot, sending a parade of housekeepers scurrying out the door, never to return. As a baby, the cherubic Howard won a modeling job for a clothing ad in Bloomingdale's. Dean believes he was paid $25 for the modeling stint, his first and last.

The family savored life at a weekend home in East Hampton, a shingled ranch overlooking a sparkling lake with wild geese. There, the Dean boys whiled away days rowing, climbing trees, and breezing down the street with a troupe of neighborhood kids who called themselves the ``bicycle brigade.''

Dean fondly recalls his upbringing but takes pains to dispel any aura of privilege. He likes to say he ``grew up in the country'' and insists that while the family was well off, they were not ``Rockefeller-rich'' and free to live a leisurely life.

``We had to work, and work hard,'' he insisted.

His younger brothers, Jim, a former marketing executive and now a fund-raiser for Dean's campaign, and Bill, a Boston investment banker, tell how their father refused to buy them baseball uniforms, leaving them the only boys on the team without: Dean's father reasoned that the boys would just grow out of them.

``Big Howard,'' as his father was known, was small of stature but blustery in personality, inspiring awe in his children and wife. A childhood bout of diphtheria left him with a deep, raspy voice he used like a trumpet to announce his arrival. His sense of humor was both boisterous and coarse: He once gift-wrapped a dead cat, jiggling it as if alive, and handed it to a relative as a birthday present.

``Uncle Howard was an extrovert and the most entertaining person I ever met in my life,'' Felch said. ``He would walk in a room and become the center of attention.''

His exuberance imbued him with a need for drama, for life on a large stage. In his second year at Yale, he dropped out, and, barred from fighting in World War II because of the diphtheria bout, he traveled to Nigeria and Sudan to run freight operations for the Allies. A photograph from the time shows him sitting in front of a tent. His hair is black and curly, his chest bare; he looks rakish and carefree.

The elder Dean returned to New York and Wall Street, eventually becoming a top executive at Dean Witter Reynolds (the founders had no relation to the family) and taking his place among the Long Island establishment, as head warden of an Episcopal church in East Hampton, a trustee at St. George's boarding school in Rhode Island, and a staunch Republican who served as campaign manager for US Representative Stuyvesant Wainwright II.

His conservatism, some say, bordered on intolerance.

``He had a lot of charm,'' said Tony Duke, a family friend who runs an educational and counseling program for black and Hispanic children from New York City. ``But I hate to use a word like he was bigoted. He made no bones about it. He taunted me sometimes. He'd say `So what are the black folks doing over there?'''

Even decades later, when the younger Dean was governor of Vermont, Big Howard would tease him about what he labeled his son's liberal politics. He joked to friends about disowning his son and expressed shock when Howard became a gay-rights hero for signing the civil unions bill.

Dean defends his father, who died in 2001: ``My father accepted people for who they were. He would make jokes about gays because everybody in that generation did, unless they were gay. He had African-American friends in the church, which wasn't common. He belonged to a club that was anti-Semitic, but he had tons of friends from Wall Street who were Jewish and they were really his friends.''

While Dean's father barreled through life, his mother tiptoed. Elegant and aristocratic, Andree B. Maitland carries herself daintily and chooses her words carefully. She met Big Howard through his prep-school friendship with her brother. She dropped out of Barnard College to marry at 18 and devoted herself to entertaining her husband's clients and rearing her boys.

She made a softer impression in her sons' lives, acting as confidante rather than agitator. But she encouraged the boys to be adventurers. When her husband was too busy working, she drove the boys on a cross-country trip to Wyoming and took them to Africa. Years later, she would return to college herself, then begin a successful appraising business.

Family friends today see signs in Dean of his father's boldness, his directness. But as a child, Howard exhibited little of it, leery as he was of clashing with his father. Instead he undertook small acts of rebellion. He tells the story of the time at St. George's when an accreditation committee came to study the school. As a student-body representative, Dean was called upon to give his opinions of the school, where all four Dean boys attended and his father would later serve as trustee.

``They expected the seniors to say how wonderful the school was,'' Dean recalled proudly. ``We did a real analysis ... and didn't mince words.''

The real rebel and domineering spirit in the house was Charlie, Dean's younger brother by two years. The two shared a bunk bed and attended St. George's together. Curly-haired Charlie bossed their two younger brothers, while Howard looked on in quiet approval. ``Charlie was much more of the leader and an extrovert,'' Dean's mother said.

Today, Dean delights in recounting his brother's assertiveness - particularly with their father.

``Charlie was very hardheaded,'' Dean said. ``He really stuck to his guns. I was more inclined to not confront people, which is interesting because I am the confrontational candidate in this race. I was uninclined to confront my father. I was more go-with-the-flow.''

Dean recalled a time in 1964 when his parents came to see the two boys at St. George's.

``We went out to dinner and my brother said that LBJ was a good president, which was heresy in my family because my father was a very strong Republican, and he kind of glared at my brother and said, `I don't think you know what you are talking about.' And he [Charlie] sort of muttered under his breath, `Well, I don't think you know what you are talking about,' which was unheard of. My father was so shocked that he didn't do anything about it, but it ruined his weekend.''

It was Charlie, too, who first branched out of the family's insular world. At 14, Charlie walked into the office of Tony Duke, the family friend who ran Boy's Harbor, and said he wanted to be part of the program. Duke gave him a job, and Charlie became close friends with many of the African-American and Hispanic youngsters.

``He was open-minded about race. I think his brother is, too, but Charlie was ahead of his generation,'' Duke said. ``I remember one night I got a call from someone from a stuffy club saying, `One of your counselors came over here with some black people.' I said, `I bet his name is Charlie Dean.'''

Dean was enthralled by the stories his father told of the ``old Yale,'' a place of parties and carousing and good fellowship.

``He said `This is where so-and-so passed out in the alley and where we had the big party. There is where so-and-so let his girlfriend out of the window when the campus police were knocking at the door,''' Dean said of his father. ``Of course I was sold. At 17 years old, that of course meant Yale was for me.''

But 1967, the year Dean started at Yale, was a crossroads in campus history. The intense ``Summer of Love,'' when sex and drugs were both forms of pleasure and protest, had made the gentle hijinks of his father's era seem quaintly outmoded. Antiwar protests surged on campus. The Black Panthers recruited young African-American student activists. Assassins took the lives of Martin Luther King Jr. and Robert F. Kennedy in the spring semester of Dean's freshman year.

Caught between worlds

It was an awkward time for legacies such as Dean's. These scions were promised the chance to follow in their fathers' footsteps, but found themselves out of step. In the eyes of some less well-heeled classmates, they were outmoded relics with no place in a meritocracy.

John F. Kerry, another son of a prominent family, had graduated a year earlier. George W. Bush was entering his senior year, insulated from change by his fraternity and a private club. But there was also Joseph I. Lieberman, son of a Stamford liquor store owner, a 1964 graduate of Yale and 1967 graduate of its law school, and later Bill and Hillary Clinton, also of Yale Law School, symbols of the new up-from-your-bootstraps ethos.

Dean now insists that ``Yale was no longer the school of George Bush but the school of Howard Dean.'' But those who knew him at college suggest he was caught somewhere between the old and new.

``He came to Yale from a prep-school background, prepared to deal with its traditional academic structures, and to lead the social existence of the old Yale,'' Peter Brooks, a Yale professor who supervised Dean's senior dormitory, wrote in a later recommendation letter. ``He instead was faced with an institution and a milieu in the throes of rapid and radical evolution, in a state of reiterated questioning of goals, purposes, and forms of commitment.

``Coeducation arrived while he was an undergraduate, and the complex of '60s political commitments reached a symbolic climax in the spring of 1970, when the agitation surrounding the Black Panther trials in New Haven was added to the Cambodian invasion.''

Dean was willing, in some respects eager, to adapt. Before starting college, he spent a year in Britain, where a friendship with a Nigerian student inspired Dean upon his return to request an African-American roommate at Yale. He ended up as a conservative alongside two of the most intense student activists on campus.

Where Dean was the third generation in his family to matriculate at Yale, Ralph Dawson and Don Roman, Dean's African-American roommates, both grew up in the segregated South. A fourth roommate, Joe Mancini, came from rural Pennsylvania, the first in his family to attend college.

``We got along fine on the surface,'' Dean said. ``We were very careful until we got to know each other. Then we talked about race all the time. But until we got to know each other, it was very difficult for everybody.''

His roommates perceived Dean as smoothly navigating the currents at Yale. His prep school background helped him organize his studies. He had a wide circle of friends and enjoyed a good party.

In fact, Dean was struggling. His grades were unremarkable and he was so unhappy during freshman year that his father had to persuade him not to drop out. He described his troubles as only ``youthful angst,'' but they sprang from a deep well. He was grappling with his own identity: While he wanted to get to know people of other cultures, the divide was sometimes wider than he imagined.

Dean's mother recalled a comment made by the roommates that took her son by surprise. ``One of them said, `I am going to learn everything I can here, and then I'm going to get everything you've got,''' she said.

Young Howard ``was certainly taken aback. He was very idealistic and wanted to learn about African-Americans and help them out and all that stuff. He didn't expect that.''

Then there was the time Dean's parents visited Yale. Dean's mother recalled walking into the dorm room, where Roman and Dawson remained on their beds. The fact that the young men didn't stand up when a lady walked into the room angered Big Howard.

``My husband was horrified because I'd go in a room and they wouldn't get up,'' she said, adding, ``He let Howard know, so there was no bringing them home.''

Roman and Dawson became officers in the black student organization, which made their dorm a magnet for African-American students. Most of the black students who visited the dorm accepted Dean. They included him in late-night card games and welcomed him in heated discussions about civil rights.

``He was not one of the blue-blood types or the private-club types who wore their school colors on their arm,'' Roman said. ``Howard was very unassuming, very low key. I think he was willing to be treated as others treated him. ... But that's not to say we didn't have our challenges.''

For one thing, Dean liked quiet and was not keen on the Motown sounds that Dawson and Roman, both members of a band, loved to blast. And Dean wasn't a political activist like Dawson and Roman. He made it clear that he believed in community service rather than protest marches. When Martin Luther King Jr. died, the four roommates spent the night talking. Dean remembered it as a sobering experience, when the men drew closer. Mancini recalled it differently: The stress of King's assassination brought back some of the same racial barriers the four thought they had knocked down.

After graduation, Dean's roommates turned their focus from politics to lucrative careers, Roman becoming a financial consultant in Atlanta, Dawson a partner at a New York City law firm, and Mancini a lawyer in Florida.

Brooks, the Yale professor, remembered Dean as a conflicted young man, one who deeply wanted to help people but felt the pull of the brokerage business.

``The last thing I said was `Howard, you are too good for them.'''

Seeking a purpose

In the summer of 1971, Dean didn't know what he wanted and had few guideposts. He was free from military service. After receiving an academic deferment while at Yale, Dean was eligible to serve - and could have been drafted in 1971, but he presented evidence of a back problem and was excused.

Choosing a career was not an immediate necessity: He had just come into a trust fund of $25,000.

``I had enough money so that if I got fired, I could live on my own,'' he said. ``That gives you an enormous amount of confidence. It serves as a security net so that whatever you do, you always have an alternative of doing something else.''

So Dean traveled to Aspen, Colo. Despite his back condition, he skied hard, proudly claiming the mantle of hotdogger, barreling down the North Face, shushing through the deep powder of the Silver Queen run. He poured concrete for spending cash, switching to dishwashing as the months grew colder. And he partied, though he won't disclose details.

``There's not much I agree with George Bush on, but one of them is that my wild and incorrigible youth has nothing to do with what would make a good president, so I'm not going to go into who did what when,'' Dean said. He later told the Globe that he did smoke some pot while in college, adding: ``But I am not getting into details.''

After 10 months, restless with resort life, Dean returned to his parents' home, still unsure of what should come next. His mother remembered encouraging him to consider business because he seemed to be reading the financial pages with interest.

Dean recalled fixating on one idea: He wanted to change the world. He saw several means toward that end, each with problems. There was teaching, discarded because an extracurricular experiment with it in New Haven left him frustrated that the children had so many needs beyond the reach of a teacher. There was medicine, discarded because it required a return to school, something he was not ready to do.

Today, Dean struggles to explain his decision to work on Wall Street but allowed that his father may have had something to do with it. ``My dad never said to me, `I want you to go to Wall Street.' But that doesn't mean he wasn't giving me subconscious clues,'' he said. ``My father was just an enormous personality and there was always a part of me that wanted to please him.''

Dean signed on with the firm of Clark Dodge as a broker and rented an apartment in New York's bohemian West Village. The early '70s was a bad time to be on Wall Street; the country was in the throes of a recession. When his work went badly, Dean switched gears, becoming assistant to the president of a small mutual fund the firm had bought. That wasn't satisfying, either.

Within a year, he'd hatched another plan: medicine. Dean says the idea probably arose because science had been a strength for him, but pressed to explain further, Dean offered no insights. He made the transition cautiously, keeping his day job and signing up to volunteer at St. Vincent's Hospital, not far from his Waverly Street apartment.

``In the emergency room, there was always something happening,'' Dean said. ``It's a bit of a war zone, constant motion. I got an eyeful.''

He enrolled in science classes at the Columbia University School of General Studies, secretly, for fear of angering his father. Eight months later, at a bistro on 86th Street, Dean told his father he wanted to go to medical school. ``To his credit, he never said what he thought,'' Dean recalled.

Whatever he said to his father that night, Dean's application to medical school paints the picture of a man sure of his decision to embrace medicine and confident in his reasoning - qualities that amply impressed admission officers and won him acceptance to Einstein.

``What do I want to be able to look back on as my accomplishments when I'm fifty?'' Dean wrote. ``I knew that the fame and power of politics was transitory, that money was worth only what it could buy and that my lifestyle would not require excessive amounts, and that teaching was rewarding because of the human contacts and service, although it did not provide the intellectual challenge I sought.

``Since I had considered medicine earlier, and rejected it because I did not feel I had the dedication, I admired those in the profession considerably... [so] I went to work in the emergency room of a hospital as a night volunteer. ... With that experience, I was able to make the decision that at fifty, I would like to look back at a career which had provided, and would continue to provide, that kind of service to others, and which was rewarded with the warmth and strength which comes from serving interests other than one's own.''

Yet the essay must be read with another essay in mind - one he had written more than decade earlier for a college sociology class.

In that one, Dean predicted that by age 40 he would be a major political leader, even specifying, wrongly, that he would be a congressman, in his second or third term.

Tomorrow: The lure of politics

Profiles of candidates in the 2004 presidential race, along with a photo gallery, can be viewed at

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