Theodore Olson, the iconoclastic appellate lawyer behind George W. Bush’s victory before the Supreme Court in 2000, died on Wednesday. He was 84.

Olson was widely condemned on the left for his role in stopping the vote count in Florida, which denied Democratic nominee Vice President Al Gore an electoral college victory to accompany his popular vote win. Bare-knuckle legal tactics from Olson plus a “Brooks Brothers riot” and infamous “hanging chads” were key to Bush’s ultimate success.

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Bush rewarded Olson with a nomination for solicitor general arguing for the United States before the Supreme Court; he was approved over fierce opposition from Senate Democrats who called him too political for the post. Olson appeared more than 60 times before the high court.

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It came as a surprise, therefore, to liberals, conservatives, and the LGBTQ+ community alike, when Olson took on the effort to strike down Proposition 8, the notorious gay marriage ban passed by California voters the same night that Barack Obama was elected president in 2008. Olson invited David Boies, his former nemesis in the Bush v Gore battle, to help overturn the ballot initiative.

“It is a conservative value to respect the relationship that people seek to have with one another, a stable, committed relationship that provides a backbone for our community, for our economy,” Olson later told the Los Angeles Times. “I think conservatives should value that.”

Olson said he endured the wrath of the conservative establishment as a result; conservative talk-show host Rush Limbaugh denounced him on talk radio and dinner invitations in Washington dried up, despite Olson’s status as a fixture in conservative social and political circles. His wife, Barbara Olson, was a firebrand conservative commentator who died in the plane that struck the Pentagon on September 11, 2001.

Olson was recruited to the Prop 8 case by actor and activist Rob Reiner after Olson told him the initiative was “wrong, morally and legally.” Others on the left thought Olson might throw the case intentionally. “I don’t take cases to lose,” he said in response.

In his opening statement in 2010, Olson argued, “What Prop 8 does is label gay and lesbian persons as different, inferior, unequal, and disfavored. It says to gays and lesbians, ‘Your relationship is not the same.’ … It stigmatizes them. It classifies them as outcasts. It causes needless and unrelenting pain and isolation and humiliation.”

Judge Vaughn R. Walker, who heard the case without a jury, went on to find Prop 8 violated the guarantee of equal protection under the law. The Supreme Court let the ruling stand, finding the plaintiffs lacked standing to bring the case. The decision helped propel the marriage equality movement that culminated in the Supreme Court’s 2015 ruling in Obergefell v. Hodges, granting the right to marriage equality nationally.

Donald Trump tried to recruit Olson twice to defend him in criminal investigations and was rebuffed on both occasions. Olson and Boies denounced Trump in an op-ed for The Washington Post over his attempts to overturn the 2020 election. The pair also wrote a memoir together, Redeeming the Dream: Proposition 8 and the Struggle for Marriage Equality, published in 2014.

Olson remained an astute political observer and source of counsel in the years following. He is survived by two children from his first marriage and his fourth wife, Lady Booth, a Kentucky tax lawyer and lifelong Democrat he married in 2006.  

“She’s working on me,” Olson told the Los Angeles Times of Booth’s effort to find his “inner liberal.”

“It’s important to be surrounded by people who think differently than we do,” Olson said. “We don’t learn anything if we surround ourselves by people who think the same way we do.”

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