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Now president and chief executive officer of the African American Cultural Center of Greater Pittsburgh, Mr. Barclay recalled a school performance of the play “You’re a Good Man, Charlie Brown.”

Because it was an all-boys school, Judge Roberts — perhaps because of his small build or a strong-natured willingness to endure ribbing from his classmates — was cast as Peppermint Patty and donned a dress for the production.

“We actually performed it for a girls school down the way, for St. Mary’s Academy,” said Mr. Barclay, whose younger brother, Paris, now a prominent Hollywood writer and producer, was cast as Snoopy in the play.

St. Mary’s, which has since closed, was one of a handful of girls schools that joined La Lumiere for occasional co-ed dances and mixers.

“We didn’t really have much of a dating thing,” said Robert MacLaverty, a lifelong friend of Judge Roberts and his senior-year roommate.

Now a prominent investment banker in Chicago, Mr. MacLaverty said he couldn’t remember whom Judge Roberts brought to the senior prom, but noted: “I think he was one of the kind who hung out with groups of guys who hung out with groups of girls.”

As far as engaging in the sort of nefarious activities stereotypical of teenagers, Mr. MacLaverty said, “In those days, the big thing was sneaking off into the woods to sneak a smoke.

“John was never anywhere near any of that,” Mr. MacLaverty said.

La Lumiere was competitive, and Judge Roberts was admitted after impressing school officials by writing in his application: “I won’t be content to get a good job by getting a good education, I want to get the best job by getting the best education.”

Former students and at least one former teacher also recalled occasionally tense interactions with students and parents from some of the rural Indiana towns whose public high schools La Lumiere competed against in sports.

“They would look at our school bus pull up and our team would get off the bus and we’d be wearing our navy blazers and our shirt and tie and they would look at that and, you know, say ‘who the [heck] are those guys,’” Mr. Kirkby recalled.