More than two decades before becoming a top contender to be President Joe Biden's Supreme Court nominee, a young Ketanji Brown Jackson sat across from Justice Clarence Thomas, reportedly perplexed by how someone of his background -- not so different from her own -- could have developed such a conservative bent.
"I don't understand you,'" Jackson, who clerked for Justice Stephen Breyer from 1999 to 2000, remembered thinking, according to a 2007 biography of Thomas, "Supreme Discomfort: The Divided Soul of Clarence Thomas."
"'You sound like my parents. You sound like the people I grew up with.' But the lessons he tended to draw from the experiences of the segregated South seemed to be different than those of everybody I know," the book, by authors Kevin Merida and Michael Fletcher, said Jackson thought as she and Thomas shared lunch.
Jackson acknowledged doing an interview for the book during her confirmation hearings last year for the U.S. Court of Appeals.
Her reported candid reflection offers a glimpse into how she perceived Thomas, a polarizing figure who may soon be her colleague, and illustrates what could be a compelling new wrinkle to the court's makeup.
If Biden taps Jackson for the role, as many commentators expect, it will be the first time two African Americans share the bench. Experts say the dissonance between Jackson, 51, and Thomas, 73, may present a fresh opportunity to explore racial identity, experience and expectations.
"We're now going to actually see at least one layer of the diversity of Black political thought in the United States -- it's going to be on display for the world to see," said Leah Wright-Rigueur, a professor in public policy at Harvard University. "That's a really big deal."
Some Black legal scholars ABC News spoke to noted why Jackson and other Black Americans who share in her cultural experience might be puzzled by Thomas' conservative judicial philosophy, which critics say has encouraged policies that have disenfranchised minority communities.
Yvette Simpson, an ABC News contributor and CEO of Democracy for America, a progressive political action committee, characterized Jackson's observation of Thomas as "an honest reflection from someone who was trying to understand a man who grew up in one world and seems to be emulating something totally different."
Experts point out that Thomas' background and upbringing bears similarities to the one that molded Jackson. Both were raised in middle- or working-class Black families in the South and attended predominantly white institutions -- including Ivy League law schools.
"[Jackson] recognizes Clarence Thomas … there's a familiarity there," said Wright-Rigueur. "They have a very similar trajectory and very similar experiences, and yet, they come to such radically different spaces politically and ideologically."
As the court's longest-serving justice, Thomas has emerged in recent years as possibly the most visible Black conservative in the country. Notoriously sparing in his comments from the bench in his earlier years, Thomas boasts an unblemished record of siding with the conservative block in politically charged cases. In the past few years, he's become one of the most loquacious justices and, as the court's senior justice, is given the privilege of asking the first questions at oral arguments.
Data shows Thomas' views conflict with a large cross-section of Black voting behavior in America. In the 2020 presidential election, for example, Biden landed 92% support from Black voters -- a figure consistent with previous national voting sentiments.
But Black voters' overwhelming support for Democrats "obscures a much more complicated story," said Wright-Rigueur. The Pew Research Center found in 2020 that a quarter of Black Democrats characterize their views as conservative.
"There's a kind of everyday conservatism that runs right through Black communities," she said. "It's just that their conservatism rarely translates into partisan support for the Republican Party."
A senior Republican Party official, who is African American, told ABC News that Thomas’ conservative disposition has been unfairly scrutinized during his time on the high court bench because he contradicts Black political norms.
"There is a notion out there that if a Black person's thought pattern, or vote, or disposition is not liberal, then it's wrong. ... If Clarence Thomas makes an opinion and it happens to be conservative, it is automatically thought to be against the Black community just because it's conservative and not liberal," the official, who declined to be named, said.
"It's a sad state when your Blackness is questioned just because of your political affiliation," the official continued, adding that Thomas' conservatism is consistent with his values, which are derived from his southern African-American upbringing.
Gender also plays a role, experts said. Conservatism in Black communities is more common in Black men, polling shows – Black women are the most consistent Democratic voting bloc of any demographic. Having a Black woman on the Supreme Court will mark a notable shift in the panel's dynamic, experts said.
"The differences in the lived experience of Black women in this country feels really significant or important to note," said Karundi Williams, executive director of Re:Power, a progressive training group. "This person will bring a different lens by which she will rule and advance our country forward. And I think that that's wrapped up in the significance of this appointment."
Some experts wondered whether the presence of a Black woman on the court might alter Thomas' staunchly conservative interpretation of the law -- one way or the other. As the lone Black voice on the court for so long, Thomas may have reveled in cultivating a streak of independence.
"When you're the only one, it does something to you -- there's a protectionism that Thomas has demonstrated," Simpson said. "I wonder if, when a Black woman joins the court, Thomas digs in -- or if she causes him to challenge the way he thinks about the world."
Biden has indicated that he would start interviewing prospective candidates for the upcoming vacancy as soon as last week, but the White House has yet to release details on his shortlist. Biden has pledged to announce his nomination by the end of February.
In an interview with NBC News earlier this month, Biden said he's done a "deep dive" on "about four people" who have already seen "thorough background checks" as he keeps an eye on replicating the qualities of the retiring Breyer.
"I'm not looking to make an ideological choice here," Biden said. "I'm looking for someone to replace Judge Breyer with the same kind of capacity Judge Breyer had, with an open mind, who understands the Constitution, interprets it in a way that is consistent with the mainstream interpretation of the Constitution."
The symbolism and historic nature of Biden's choice will far outweigh the nominee's relationship with Thomas, compelling as it might be, experts said. Not only will the new justice break an important barrier, but after three decades of Thomas as the sole Black presence, a new voice more in line with the overwhelming views of that demographic will usher an important new era of representation on the court.
"Ten years ago, the idea of two Black people being on the on the Supreme Court at the same time was laughable -- it just wasn't going to happen," Wright-Rigueur said. "And now it's actually happening, so we actually get to see [the diversity of Black political thought] play out."
ABC News' Devin Dwyer contributed to this report.