Ted Olson has argued before the Supreme Court 65 times, on some of the most consequential cases of the last quarter-century, making him as close as an attorney can get to a household name.
His first appearance was as an assistant attorney general, in 1983: "I remember every word vividly. I remember the preparation. I remember breaking my glasses the day before the argument, thinking, 'How can this happen to me?'"
Correspondent Mo Rocca asked, "Was it out of nervousness that you broke them, you think?"
"Of course, it was nervousness. Anybody that argues in the Supreme Court is going to be nervous, no matter whether it's your first time or the 50th time. You're going to be nervous."
A star in conservative legal circles, Olson, a California native, went to law school at Berkeley, a locus of liberal activism in the 1960s.
Rocca asked, "Did you feel like an outlier at Berkeley?"
"Well, those of us who were Republicans, which was a very small minority, I think we were treated quite well. Most of the people thought of us as curiosities."
The public came to know Olson when he represented the Bush side in Bush v. Gore, the case that decided the 2000 presidential election in George W. Bush's favor.
Rocca asked, "Why did the Bush side win?"
"We were right," Olson replied.
After serving as President Bush's solicitor general, Olson left the government, and in 2010 argued on behalf of the political group Citizens United. "We hope the court will come out strongly in favor of the first amendment right of all citizens, including corporations and unions," Olson said.
In its ruling, the court struck down limits on political spending – and the group's name became shorthand for outrage about big money in politics.
But at least two of his subsequent cases surprised many on the right.
First, he teamed up with David Boies, his opponent from Bush v Gore, to overturn California's ban on same-sex marriage in 2013. "This is a matter of fundamental human rights and human decency," Olson said. "The equal protection of the laws is the protection of equal laws. It is not something that's partisan or anything like that; it's about American values."
Olson told Rocca, "The first question we were being asked by people in the media [was], 'Why did you come together?' And that gave us the opportunity to explain what was wrong with this discrimination."
And in 2019, in the so-called "Dreamers" case, Olson represented a group of immigrants brought to the United States illegally as children and now threatened with deportation.
"I went and spent time with these people, and each one told their story – where they came from, when they came to the United States, what it would mean for them to be wrenched away from their family or their job and sent to a country that they did not know," he said. "And I felt very keenly the stories of these individuals. And I thought, I have got to win this case."
Olson won that one, too. But his involvement in the Dreamers case added to speculation that the Republican stalwart was going "soft."
"A lotta people like to say, 'Oh, I had influence on him as a Democrat or as a liberal-thinking person,'" said Lady Booth, an attorney from Kentucky – and Olson's political opposite.
The two met in 2002: "The person fixing me up with him said, 'No, no, no, he was one of the attorneys in Bush v Gore. He's brilliant.' I pulled the tapes, the VHS tapes out of my closet and, 'Oh my gosh, he was representing Bush, not Gore?' Yeah."
"You had that trial taped?" asked Rocca.
"I did, geek that I was."
The couple's first date was just a few months after the September 11th attacks, which left Olson widowed. Olson's then-wife, Barbara, a prominent conservative commentator, was on the plane that hit the Pentagon that day.
In the terrible weeks that followed, Olson turned to his mother for counsel: "We had lost my father, her husband, a few years before. And she had immediately started meeting people and dating people. And she took me aside and she said, 'Ted, it's time for you to get out and meet people, socialize. You're a young man.' And I said, 'Mom, I'm 60 years old!' And she said, 'I'm 80! I think that the best way of respecting the person that you loved and that you lost is to get out and live.' And look how lucky I was."
Ted and Lady married in 2006. They say their "mixed marriage" is proof that people are more than their party affiliation.
"She's got her own mind," Ted said. "And she's got more law degrees than I do. We can talk about some things. But I'm not gonna try and persuade her of my point of view on anything. Except maybe where we go on vacation or something."
And despite the talk, Olson insists he hasn't changed.
Rocca asked, "If people look at the chronology of the cases you've won – there's the Ted Olson of Bush v. Gore and Citizens United; there's the Ted Olson of Prop 8 and the Dreamers case. Are those the same Ted Olson?"
"Well, Lady will tell you that it's all because of her!' he laughed. "The good arguments and the good cases and the noble causes are because of Lady."
"But were you conservative then and conservative now?"
"I would answer it one way. I think I've always been a conservative. People tend to want to put people in boxes, and people overdo the conservative or liberal thing."
Now 80, Ted Olson says he's unlikely to argue another case in front of the Supreme Court. But he still believes that making a good argument is possible without being at each other's throats – something he learned back in college debate class: "The idea of the analysis and trying to understand both sides of an issue and being persuasive on this side, and then being persuasive on the other side."
"That really stretches a mental muscle, right?" asked Rocca.
"I think that's a very good thing for people to do. In today's world, people are so polarized, and there's not a lot of time spent trying to think the way the other side thinks, or try to express what the other side is expressing and believing. I think it would probably be good for all of us."
Story produced by Mark Hudspeth. Editor: George Pozderec.
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