Sandra Day O'Connor, left, in 1950, and William Rehnquist, right, in 1948, both pictured in the Stanford University college yearbook.
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In an excerpt of his book “First” — a biography of Sandra Day O’Connor — author Evan Thomas unearthed something amazing: A letter from William Rehnquist to Sandra Day asking her to marry him. “To be specific, Sandy, will you marry me this summer?” Rehnquist wrote in the letter from 1952. Day, who was by then dating a man named John O’Connor who she would go on to marry, declined. (The proposal wasn’t totally out of the blue; Day and Rehnquist had dated for a time when they were both at Stanford Law School.)

I wanted to know more. (Who wouldn’t?) So I reached out to Thomas to talk about the marriage proposal, the two justices and how they co-existed on the nation’s highest court for more than two decades.

Our conversation, conducted via email and lightly edited for flow, is below.

Cillizza: How much did you know about the relationship between Sandra Day and William Rehnquist before this book?

Thomas: Both Sandra O’Connor and William Rehnquist had publicly said that they had “dated” in law school and “gone to a few movies together.” But about three years ago, when I began interviewing Justice O’Connor’s friends for a biography (to be published by Random House in March), one of her close friends, Cynthia Helms, told me that the relationship had been more than that. She said that after O’Connor resigned from the court in 2006, she told Helms that Chief Justice Rehnquist, who died in 2005, had asked her to marry him when they were in law school.

Cillizza: The proposal letter. How did you find out it existed? And how did you track it down for the book?

Thomas: For my biography, I had the full cooperation of Justice O’Connor and her family. She allowed me to see her papers, which are still closed, at the Library of Congress, and I was also shown a box of correspondence that was kept in the chambers she maintained at the Supreme Court as a retired justice. In the box of correspondence, I found lots of family letters, but also 14 letters written from Bill Rehnquist to Sandra Day between January and October 1952.

It was clear from the letters that Rehnquist had dated Sandra during their first year of Stanford Law School, in the spring of 1950, and they had broken up in the fall of their second year, though they remained good friends. In January of 1952, Rehnquist, who was generally acknowledged to be the top student in the class (with Sandra not far behind), graduated early to take a Supreme Court clerkship with Justice Robert Jackson. From Washington, he began writing ever more ardent letters to “Sandy” back in law school, and in March asked her to marry him. She did not say no until July.

She had fallen in love with another law student, John O’Connor, but he had not yet proposed to her – and she had already been through two other broken engagements. (In those more chaste days, there were a lot of marriage proposals.) Rehnquist was at first wounded by her rejection but quickly recovered, and they became good friends again. John proposed to Sandra in early September and they were married in December. Rehnquist began dating his eventual wife, Nan, and the O’Connors and Rehnquists became lifelong friends, in Phoenix, then in Washington.

Cillizza: The two served together on the Supreme Court for more than two decades. What was that like?

Thomas: When O’Connor came on the court in 1981, she was a little surprised and hurt that Rehnquist did not do more to help her. But he was seriously ill with back troubles. They soon became friendly colleagues. O’Connor often voted with Rehnquist on the conservative wing of the court, though as time went on, she became somewhat more liberal. Other justices could see that O’Connor and Rehnquist were personally close and teased each other at the justices’ weekly lunches.

Cillizza: One other story from that period amazed me. Sandra Day and her eventual husband, John, courted while proofreading over beers???? What else do we know about that?

Thomas: John O’Connor recalled that, as a second-year law student and new editor on the law review, he was assigned to cite-check an article with Sandra Day, a third-year student. He asked her out afterward for a beer. They went out the next 40 nights in a row.

Cillizza: Finish this sentence: “The reason no one knew about the marriage proposal between two former Supreme Court justices is _________.” Now, explain.

Thomas: … “because O’Connor and Rehnquist didn’t tell them.”

Not even their families knew. They may have thought it was wise to be discreet. The other justices had some idea that the two had dated in law school. When O’Connor joined the bench in October 1981, Harry Blackmun leaned over and whispered to Rehnquist, “No fooling around.”