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The serendipitous path of Roberta Kaplan

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Roberta Kaplan

The serendipitous path of Roberta Kaplan

Roberta Kaplan was once described by Arianna Huffington during a live interview at Fortune as “a powerhouse corporate litigator.”

In the corporate legal field, brilliant litigators are a dime a dozen. But what differentiated Kaplan was that she met Edie Windsor and the two teamed up in a David and Goliath kind of a legal case.

With Windsor, Kaplan entered the history books in 2013 when the Supreme Court invalidated certain sections of the Defense of Marriage Act (DOMA) in the case of United States v. Windsor.

This case later led to the Supreme Court ruling in Obergefell v. Hodges two years later that struck down all barriers to same-sex marriage across the US.

For a lot of the LGBT people, it was serendipity: the fearlessness of Windsor partnered with the passion of Kaplan.
Thanks to these two lesbians, America could now enjoy the rights of same-sex marriage.

The young Roberta Kaplan

Roberta “Robbie” Kaplan grew up in Cleveland, Ohio. In 1988, she graduated magna cum laude in Harvard University and in 1991, a law degree at Columbia University.

She started as a law clerk for Judge Mark Wolf from Massachusetts before moving to the New York Court of Appeals for Judge Judith Kaye, where she was able to master academic articles.

She began working for Paul Weiss in 1996 and became partner in 1999 where she handled sensitive court cases for Citibank, AIG, Fitch Ratings, JP Morgan Chase, and Airbnb.

Roberta Kaplan comes out

All her life, Robbie knew she was a lesbian but the first time she kissed a girl, she was 24 years old and had already graduated law school.

However, like the rest of us, she was scared: scared of coming out, scared of being a lesbian, and scared of not having a normal life.

In Columbia, she was a bit of a homophobe, calling out on a girl for the simple reason that she was secretly in love with the girl.

It was in 1991 that she decided to come out to her mother, who didn’t take it well and banged her head on the wall when Robbie told her.

Because of this disastrous coming out and the fear she faced of living a lesbian life, she sought therapy under Thea Spyer.

Spyer, at that time, was already in a 25-year relationship with Edie Windsor and told Robbie about the fulfilling life she led with Windsor.

Roberta Kaplan wins the case

Eighteen years later, Robbie would cross paths with Edie again– and again, it was through Thea.

Taxed with over $350,000 for the estate Thea left to Edie, Windsor went from one brilliant lawyer to the next seeking legal help.

She was turned down for a lot of reasons, from “the time is not right” to the case being weak because Edie wasn’t exactly incapable of paying the taxes. Some just gave her the cold shoulder.

When Robbie was asked to help Edie, she wasn’t only eager, she was excited because she knew Thea from years ago and of Edie from Thea’s stories.

She offered to take the case pro bono. With her passion for the case and for the cause, she focused not on the LGBT side of it but the unfair taxation. She also used the life of Edie as the case.

People who have seen Robbie paint the story of Edie and Thea were mesmerized by her passion, her soulfulness, and her brilliance.

She won the case nobody wanted to take, and the rest, as they say, was history.

As for Kaplan? Robbie managed to come out and she married her partner Rachel Lavine in 2005 in Toronto. Their son, Jacob, is ten years old.

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