ONANCOCK, Va. — When the United States Supreme Court ordered school districts in 1968 to dismantle their segregated classrooms, Wescott and Nancy Northam had a choice to make.

As in much of the rest of the country, private schools had popped up in the Northams’ community on Virginia’s Eastern Shore. They were havens for white parents who did not want their children in the same classrooms as black students. Mr. Northam was a lawyer, his wife a nurse, so that option was well within their means.

But the Northams — whose ancestors were among the many white slaveowners to lay roots in this rich agricultural region in the early 1800s — made what seemed like a surprising decision for people of their stature.

They kept their sons, Thomas and Ralph, in public schools.

In a region where black and white people largely lived in different communities, Ralph Northam hung around black neighborhoods with black friends. He was one of two white players on the high school basketball team in 1977, his senior year. His class had 73 students — 37 black, 36 white.

“When Ralph came up, we were chasing footballs,” said Robert Garris Jr., who is black and a friend from childhood. “We were chasing basketballs, baseballs. We were fishing. We were crabbing. We didn’t see race.”

Many people are now wondering how this same Ralph Northam, now the governor of Virginia, could be the man who ended up with a racist photograph on his page in a medical-school yearbook. How he could have thought it a good idea to darken his face with shoe polish to moonwalk like Michael Jackson in a contest in the early 1980s. How he could have been unaware of the deep and resonant pain associated with blackface among the African-Americans he represents, until a staffer told him about it during his most recent campaign.

As Mr. Northam, Virginia and the national political establishment grapple with what’s next for him, an examination of his early life in the secluded, rural fishing town of Onancock, Va., provides some clues about what shaped his perspectives on race, and how he could have fallen so short in his understanding.

Though classmates from medical school and many people outside of Onancock are calling on him to resign, many of those who know him well from his hometown are pushing back against demands that he step down.

Mr. Northam, 59, came of age in Virginia in the 1960s and ‘70s, when it hardly would have been shocking to see white people darken their faces for costumes, several people who knew him said. He lived in a place where students could attend movies and eat together across racial lines, but did not openly date outside their race.

As a pediatric neurologist and volunteer medical director at a children’s hospice, Mr. Northam visited the homes of hundreds of African-American families in crisis. And yet, many people who know him best now worry that he may have missed some basic lessons about the struggles of his black neighbors. Gerald Boyd, who is black and has lived on the Eastern Shore since 1951, said Mr. Northam’s case was a cautionary tale that the nation’s racist conditioning can snare even well-meaning people.

“That conditioning slips out in the form of thoughts and feelings and words, jokes and deeds,” he said. “Until white people have a chance to talk about how they have been conditioned, it’ll sneak up on them.”

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The Eastern Shore of Virginia, a jagged peninsula bordered by Maryland on its north, feels like an isolated outpost. Until 1964, when a 20-mile-long bridge-tunnel opened, it was directly accessible to the rest of Virginia only by ferry.

Landowners in Virginia owned more enslaved Africans than those in any other state, and the Eastern Shore was no exception. Around 1860, Accomack County, which includes Onancock, had the highest percentage of free black people in Virginia, said Dennis Custis, a former history teacher at Onancock High School. Neighboring Northampton County, the other county on the Eastern Shore, had the highest percentage of enslaved African-Americans, he said.

Mr. Northam’s great-great grandfather, James Northam, was among the Eastern Shore’s slave owners. Mr. Northam’s father, Wescott Northam, learned this several years ago during a search for land records, but he considered the information simply “a matter of history,” the elder Mr. Northam, now 94, told the Richmond Times-Dispatch. Despite the family’s long Virginia history and the presence of African-Americans with the last name Northam in the area, Ralph Northam told the Richmond paper that he didn’t learn that his ancestors had been slaveholders until 2017, during his campaign for governor.

“My family’s complicated story is similar to Virginia’s complex history,” he said. “I have led my life,” he said, “to help others, and really not see color as an issue.”

Generations after slavery ended, Ralph Northam entered a world still shaped by it.

He grew up in a red brick house at the end of a long driveway shaded by a canopy of towering pine trees. His family’s farm, about 10 minutes outside of Onancock’s tiny downtown, was in an area with mostly white residents. In 1970, Accomack County, population 29,000, was 37 percent black and 62 percent white.

Mr. Garris, now a church pastor, said black people were not welcome in certain communities in the county, and needed to be cautious around white people. He recalled when his basketball team traveled to Tangier Island in Chesapeake Bay for games, his coach would offer a stern warning.

“Pay attention to the ball, pay attention to the game, don’t let your eyes wander up into the stands,” Mr. Garris, who graduated from Onancock six years after Mr. Northam, recalled his coach saying. “If they catch you looking at a white girl, they might not take it kindly.”

At the direction of the state’s Democratic political machine and the urging of its allied editorial pages, Virginia fought a “Massive Resistance” campaign against court-ordered public school integration from the mid-1950s through the mid-1960s. In 1968, when Onancock High School was still predominantly white, Jack Johnson was hired as one of the school’s first black faculty members. An art teacher, Mr. Johnson grew up in a part of North Carolina where, as a black man, he was physically attacked.

Resistance to integration wasn’t as violent in Onancock as it was in many other parts of the state, but there were rocky moments, said Mr. Johnson, now 77. He recalled a white girl calling a black boy the N-word, and the boy striking the girl. Mr. Johnson said he intervened to ensure that both children were punished, and not just the black boy.

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Mr. Northam started at Onancock High School three years after full integration in 1970. He came with a wry, if awkward, sense of humor. He was the guy who made faces from the church pews to make the choir girls laugh, and who bluntly approached a friend’s crush on the bus and asked her to go speak with his friend.

“Growing up, the way we were raised, my brother and I, we didn’t see color,” Mr. Northam, who declined to be interviewed for this article, said in a video posted on The Daily Times website in January.

Students would tease one another about all kinds of things, but “anything about race would have been a casual observation,” said Jarvis Bailey, 57, who is black and graduated two years after Mr. Northam. Yet students were not blind to issues of race.

Harry Mears, 54, said that one of his black friends would jokingly call him a “white cracker” and he would call the friend an oreo, a slur for a black person seen as too close to white people.

“We all did that,” said Mr. Mears, who graduated a few years after Mr. Northam and rode the same school bus. “We were all friends. We didn’t say anything to hurt each other.”

Mr. Mears recalled that when he was 17, he told his parents he was thinking about dating a black girl he liked. “They just said that they would appreciate it if I didn’t,” he said. “I respected their wishes.”

Robert Leatherbury, who is white and went to the same church as Mr. Northam in Onancock, said he used to call Mr. Northam “coonman,” but could not recall why. He knew back then that it could be taken as a slur, but “I didn’t mean it in that way,” he said.

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History classes at Onancock touched only briefly on racist imagery.

“I would give an explanation of the origin of Jim Crow,” believed to be one of the first popular blackface characters, said Mr. Custis, the Onancock history teacher.

Mr. Mears recalled that when he was about 11, a white child dressed as a basketball player in blackface came to his house on Halloween.

“We were not that far into even having the opportunity to vote, so for a white person to find it acceptable, it’s not that hard to believe,” Mr. Bailey, the former classmate, said of blackface. “I don’t know that a person in that era would equate putting on makeup as putting on blackface.”

“I’ve always known that blackface is offensive,” said Carla Savage-Wells, who was president of Mr. Northam’s class at Onancock. “I don’t think anybody, if they knew I was coming to a party, would be bold enough to show up in blackface. They certainly would know that I would be one of many who would address it if they did.”

Mr. Northam said in his news conference last week that he did not grasp the broader significance of “blackfacing” until a black aide explained it to him during his gubernatorial campaign.

On Sunday, Mr. Northam told Gayle King, one of the hosts of “CBS This Morning,” that “I have thought about resigning, but I’ve also thought about what Virginia needs right now.

“Virginia also needs someone who is strong, who has empathy, who has courage and who has a moral compass. And that’s why I’m not going anywhere,” he said.

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On the Eastern Shore, the revelations have sowed confusion and pain.

David and Cathy Riopel, pediatricians at the Franktown Community Health Center who are white, recalled how, for a decade beginning in the mid-1990s, Mr. Northam commuted 60 miles each way to treat the children at the center, including many from African-American, Latino or Haitian families who worked on the region’s farms or in its chicken processing plants.

When Mr. Northam entered politics, “people coming in would be very upset about not being able to see him,” Ms. Riopel recalled. “We would have to reassure them that he was still helping us,” and, “that he was still on our side.”

“In politics, it seems, you can’t have anything in your past — and this is potentially something major in his past,” Mr. Riopel said. “But his lifetime of work and what he has accomplished stands for something.”

Mr. Bailey, Mr. Northam’s black schoolmate, served in Desert Storm, as did Mr. Northam, who was an Army doctor. Mr. Bailey retains a vivid memory from 1988, when his wife, Monica, was in Walter Reed Army Medical Center in Washington, recovering from having delivered a stillborn child. “As God would have it, Ralph was doing a rotation at Walter Reed, and he found us and spent time,” Mr. Bailey, now a high school administrator, recalled.

People on the Eastern Shore “are sick about this,” he said. “We’re small, we’re not really known for a whole lot, and now we’ll be known for this.”

He is angry at the wave of Democrats who called within hours for Mr. Northam to resign.

“Racism is wrong,” Mr. Bailey said. But how ironic in a polarized nation, he said, that “the only folks who are going to give him the benefit of the doubt are those who have less to lose.”

Sarah Mervosh contributed reporting. Kitty Bennett and Doris Burke contributed research.

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