Nerdy Geniuses, Sewing Kits & the Supreme Court’s ‘Sadistic’ Rule: Roberta Kaplan on Her Historic Windsor Win

Roberta Kaplan recalled the first time she met the women that would be at the center of Kaplan’s historic U.S. Supreme Court win in United States v. Windsor, which struck down the federal Defense of Marriage Act.

In the wake of the Supreme Court's decision in Windsor, federal and state courts struck down state same-sex marriage bans almost unanimously, culminating in the high court’s decision last term confirming a national right for same-sex couples to marry in Obergefell v. Hodges.

Kaplan lived close to Edie Windsor in New York City’s West Village, so she decided to just walk over to Windsor’s house for their first introduction.

In her mind, Kaplan had an image of Windsor—who had worked as a software programmer at IBM—as a “nerdy math genius,” she told a live audience Sept. 16 during an interview for Bloomberg Radio.

But when Windsor opened the door, she saw a perfectly manicured woman, with a short, blonde bob, Kaplan described. And she turned out to be incredibly articulate too, Kaplan added.

Although Kaplan said that she didn’t imagine that she’d be arguing for Windsor at the U.S. Supreme Court when she first met her—Kaplan said that would be insane given that it’s a “crapshoot” to get your case before the justices—the high court wasn’t completely out of her mind.

If she could just get the justices of the Supreme Court to think about Windsor’s marriage to Thea Spyer as just like their own marriages, Kaplan was confident they would win.

The legal issues involved aren’t “legal rocket science,” she explained.

Those legal issues—that marriage for same-sex couples was a fundamental right and that the denial of such marriage was a violation of equal protection—ultimately prevailed in Windsor and Obergefell, Kaplan said. 

But in 2009, those arguments weren’t prevailing yet. And so, the self-proclaimed trial lawyer focused on the facts.

On that front, Kaplan said she thought Windsor was the perfect plaintiff. But other stake holders didn’t agree.

Some thought she was too rich, Kaplan recalled. After all, she was fighting a more than $300,000 tax bill.

Windsor wasn’t able to take advantage of a federal estate tax exemption for surviving spouses because the federal government didn’t recognize her marriage to her spouse, whom she’d been in a relationship with for more than 40 years. In particular, DOMA defined marriage as between only a man and a woman for all federal purposes.

Kaplan admitted that having to pay such a high tax bill wasn’t a problem that most Americans had to tangle with. But most Americans do take issue with unfair taxes—that’s what kicked off the Revolutionary War, she pointed out.

Here, Windsor was taxed for being gay, Kaplan said.

Those compelling facts were one reason she thought the justices agreed to hear her case, even though there were three similar cases before the justices at the same time, Kaplan said.

Well, that … and the U.S. Solicitor General told the Supreme Court it should accept her case, she added.

The executive branch’s role in the case was unique. At some point during the litigation, it decided not to continue to defend DOMA. The Bipartisan Legal Advisory Group of the House of Representatives stepped in to defend the act.

Kaplan said that the government’s decision not to defend its own law was one of the most surprising moments of her life.

She recalled mentioning that to President Barack Obama. He responded: “Yeah, I never get any credit for anything,” presumably referring to his behind-the-scenes role in the downfall of the act.

But before the law could fall, Kaplan had to argue the case before the high court.

She said that on the day of the argument she was in a “state of high anxiety.”

She recalled being in the lawyers’ lounge before the argument and getting the customary speech from the court clerk.

The speech was always the same: We have cough drops, call the justices by their correct name … practical things like that, Kaplan said.

But one bit of information struck her as odd: the court has a sewing kit available for the arguing attorneys.

A sewing kit? If one of her buttons was going to come off right then, then it was just going to have to come off, Kaplan said. “There’s no way I can sew right now!” she said, adding that she’d have a thousand cuts if she tried to do that before the argument.

All buttons intact, she acknowledged that she was a little shaky for the first few minutes of the argument. But eventually she got into the groove.

She recalled one exchange during the oral argument that she said was a defining moment.

Her adversary, Paul Clement—who she said was one of the finest Supreme Court advocates of her generation—was arguing when Justice Ruth Bader Ginsburg accused Clement of relegating same-sex marriages to “skim milk marriage.”

“That’s what our whole case was about,” Kaplan recalled.

But she admitted that her brief and oral argument were really focused on often swing-Justice Anthony M. Kennedy, who ended up writing the majority opinions in both Windsor and Obergefell.

She said her legal team had sort of a “Kennedy’s Greatest Hits”—a list of quotes from his previous gay-rights opinions.

“[T]imes can blind us to certain truths and later generations can see that laws once thought necessary and proper in fact serve only to oppress,” was the one Kennedy quote that Kaplan was able to invoke during the argument—a quote that came from Kennedy’s opinion in Lawrence v. Texas, 539 U.S. 558 (2003).

Kennedy himself cited to Lawrence in his majority opinion in Windsor.

Kaplan said that when she heard that Kennedy wrote the opinion, and that Scalia wrote a dissent, she knew she had won.

But Kaplan wasn’t at the court that day.

The Supreme Court has this kind of “sadistic” rule where they won’t tell you when a decision in your case will be handed down, Kaplan said. You just have to go down to the court each day you know they are releasing opinions.

Because Windsor was experiencing health problems that precluded her from traveling frequently, Kaplan didn’t make the trek to D.C. for the decision.

Instead, she, Windsor and others gathered around her kitchen table each morning the court was handing down opinions at 10 a.m.

When they heard the news, Kaplan said it was pandemonium.

Kaplan said that she’s gotten more comfortable with her role in history. But every now and then, she still says to herself, “I can’t believe I did that!”

Kaplan has an upcoming book on her experiences, “Then Comes Marriage.”

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