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President Bill Clinton had just beat Republican incumbent George H. Bush and the first family was facing an early political test: Where would they send Chelsea Clinton, their 12-year-old daughter and only child, to school?

On the campaign trail, Bill Clinton had portrayed himself as an ardent supporter of public education. He even sent his daughter to Horace Mann Magnet Middle School, a public school in Little Rock, Arkansas where 59 percent of the students were black and 41 percent white.  (Today, out of some 760 students, 58 percent are black, 26.5 percent are white, 11.7 are Hispanic and 1.7 percent are Asian.)

Local Washington, D.C. officials invited the first family to choose a city school as a show of good faith. But days before Clinton’s inauguration, the family announced that Chelsea would be attending one of the region’s most exclusive private institutions: Sidwell Friends School.

“It’s an academically challenging school,” Clinton spokesman George Stephanopoulos said at the time. “And it’s a school that Chelsea and her parents feel that she’ll be challenged and productive and happy in.”

• Read more on the live blog: The 74 and Bellwether Education Partners are partnering to cover both the Republican and Democratic National Conventions.

Chelsea Clinton would join an elite group of students that included the children of  Washington Post publisher Donald E. Graham, former New Mexico Sen. Jeff Bingaman, and New Jersey Sen. Bill Bradley.

Criticism of the Clintons’ school choice was swift and broad.

Michael Casserly, the executive director of the Council of the Great City Schools, a Washington, D.C.-based coalition of city public school systems, called the Clintons’ decision an “unfortunate vote of no confidence in urban education.”

Enrolling Chelsea in a public school “would have been an excellent opportunity to spur greater parental involvement in urban public schools and to work hand in glove with the public schools from both a political and personal standpoint” he said.

Former D.C. school board member Sandra Butler-Truesdale told The Washington Post that if Clinton had picked a public school, “it would have boosted the morale of educators in this city. It would have made such a big difference in the way education is delivered.”

Rebuke also came from national political figures. Then-Secretary of Education and now U.S. Sen. Lamar Alexander told CBS Morning News that the first family made a wise choice for their daughter — Alexander’s son had just graduated from Sidwell Friends — but were being hypocritical because Clinton opposed Republican calls for school vouchers that would have helped needy parents make a similar choice.

Bill Clinton had argued that vouchers would drain money from public schools; Hillary Clinton also opposes the policy.

With tuition at Sidwell Friends back then more than $10,000 a year, some 27 percent of its 1,030 students were minorities when Chelsea Clinton was admitted. Sidwell Friends remains  popular among Washington’s powerful families, most famously President Barack Obama’s daughters, Malia and Sasha. The school’s tuition has risen to $39,360, with only 23 percent of students receiving any kind of financial aid, according to the its website. The school was founded in 1883 by Thomas W. Sidwell to uphold the Quaker principles of peace and justice.

Even former president Jimmy Carter, who was the first president in 71 years to send a child to a D.C. public school while in office, said he was “disappointed.” His daughter, Amy, attended public schools throughout her four years in Washington, including Stevens Elementary School and Hardy Middle School, a predominantly black school. Amy Carter went onto Brown University but was asked to leave her sophomore year. She finished at Memphis College of Art and then got her master’s at Tulane University.

Chelsea went onto Stanford University (and Columbia and Oxford); Malia will enter Harvard in fall 2017 after taking a gap year. The Bush daughters, Jenna and Barbara, had both graduated from Austin High School in 2000, the spring before their father took office. Jenna went onto the University of Texas and Barbara became the fourth-generation Bush to attend Yale.

Amid the Sidwell storm, the Clinton family defended the choice saying, “we believe this decision is best for our daughter at this time in her life based on our changing circumstances.” Hillary Clinton added later that a private school would allow the family to better maintain Chelsea’s privacy—a sentiment she reiterated in her 2003 memoir, “Living History.”

“Our decision about where to send Chelsea to school had inspired passionate debate inside and outside the Beltway, largely because of its symbolic significance. I understood the disappointment felt by advocates of public education when we chose Sidwell Friends, a private Quaker school, particularly when Chelsea attended public schools in Arkansas. But the decision for Bill and me rested on one simple fact: private schools were private property, hence off limits to news media. Public schools were not. The last thing we wanted was television cameras and news reporters following our daughter throughout the school day as they had when President Carter’s daughter, Amy, attended public school.”

The press during Bill Clinton’s administration would, in fact, develop a general no-coverage rule when it came to the First Family’s children.

On Chelsea’s graduation day from Sidwell, though the Clintons did not seem to mind the public attention. During a two-hour outdoor ceremony, President Clinton gave a short, bittersweet talk in which he instructed the high school graduates to “indulge your folks” if they seem sad as they remember all the milestones their children have reached. Obama actually declined an invitation to speak at Malia’s graduation, saying he would be wearing dark glasses and crying.

Hillary Clinton also waxed nostalgic in her syndicated newspaper column that week: “Like parents across the country,” she wrote. “We find ourselves fighting back tears as we contemplate what our days will be like when our daughter leaves the nest to embark on a new stage of life.”

Tonight, it will be Hillary embarking on a new stage of life — and history — when Chelsea introduces her mother, who will make her acceptance speech at the Democratic National Convention.

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This article was published in partnership with The74Million.org.