Theodore B. Olson, a leading Supreme Court litigator who built a sturdy reputation as a conservative power lawyer during the 1980s and ’90s, and then surprised colleagues and foes alike when he took up traditionally liberal causes like gay marriage and the children of undocumented immigrants, died on Wednesday in Fairfax, Va. He was 84.
Lady Booth Olson, his wife, said the cause of death, in a hospital, was a stroke.
Mr. Olson’s conservative bona fides were unquestionable. On the wall in his office hung a photograph of President Ronald Reagan, under whom he led the Office of Legal Counsel; it carries the inscription “With Heartfelt Thanks” — presumably for leading fights on Republican priorities like rolling back affirmative action, school busing and government regulations.
Nearby was a medal given to him by the Defense Department, in honor of work he did as solicitor general under President George W. Bush, including defending the president’s broad claims to executive power following the Sept. 11 attacks — during which Mr. Olson’s wife Barbara Olson was killed on the hijacked plane that crashed into the Pentagon.
He was a founding member of the Federalist Society, the influential conservative legal group, and a leading figure in many conservative legal triumphs of the 2000s, including Bush v. Gore (2000) and Citizens United (2010).
It was therefore a shock to many when, in 2009, Mr. Olson signed on to a lawsuit against the state of California over Proposition 8, a ballot initiative banning same-sex marriage that had passed in 2008.
At first, some gay-rights activists accused him of taking on the case in order to sabotage it, while opponents began to flood his inbox with homophobic emails. Mr. Olson stuck with it, insisting that defending gay marriage was consistent with his brand of small-government conservatism.
“For conservatives who don’t like what I’m doing, it’s, ‘If he just had someone in his family we’d forgive him,’” he told The New York Times in 2009. “For liberals, it’s such a freakish thing that it’s, ‘He must have someone in his family, otherwise a conservative couldn’t possibly have these views.’ It’s frustrating that people won’t take it on face value.”
Mr. Olson, who saw the case as a potential legal landmark, devised an aggressive strategy that spread far beyond the courtroom. He brought on the liberal superlawyer David Boies, his rival from Bush v. Gore, as co-counsel, and as a sign of bipartisan unity.
He found four sympathetic, telegenic clients — a gay couple and a lesbian one — and hired a documentary film crew to follow them as they navigated their way through the legal system, ultimately prevailing before the Supreme Court in 2013. Two years later, the court ruled that gay marriage was a constitutional right.
Mr. Olson’s position on same-sex marriage was not a one-off. Over the following decade, he took on a number of cases that surprised people used to thinking in strictly left-right terms, but which he insisted were consistent with his belief in civil liberties.
Among them was the Deferred Action for Childhood Arrivals program, known as DACA, which gave amnesty to the children of undocumented immigrants, or “dreamers.” Despite his earlier defense of broad government powers, Mr. Olson successfully opposed the Trump administration’s attempt to shutter the program.
“Executive power is important, and we respect it,” he told The Times in 2019. “But it has to be done the right way. It has to be done in an orderly fashion so that citizens can understand what is being done and people whose lives have depended on a governmental policy aren’t swept away arbitrarily and capriciously. And that’s what’s happened here.”
Theodore Bevry Olson was born on Sept. 11, 1940, in Chicago to Lester Olson, an engineer for United Airlines, and Yvonne (Bevry) Olson, a poet and teacher.
His family moved to Mountain View, Calif., soon after he was born. He graduated from University of the Pacific, in Stockton, Calif., in 1962 with a degree in communications and history.
His political views emerged in college, centered on a particularly Western, libertarian brand of conservatism. During a debate trip to Texas, he watched as a restaurant manager in Amarillo refused to seat a Black teammate. Mr. Olson shouted down the manager, telling him they would all leave if he wouldn’t serve everyone.
After college, Mr. Olson went to law school at the University of California, Berkeley. He was one of a handful of students at that famously liberal campus who campaigned for Republican Senator Barry Goldwater for president in 1964.
Following his graduation in 1965, Mr. Olson went to work for the Los Angeles office of the law firm Gibson, Dunn & Crutcher (now Gibson Dunn). Aside from his time in government, he never left the firm.
In 1981, Mr. Reagan named William French Smith, a senior partner at the law firm, as his first attorney general. Mr. Smith brought two acolytes, Mr. Olson and Kenneth Starr, along with him to Washington.
The two joined a tide of young conservative lawyers pouring into Mr. Reagan’s Washington, eager to remake the federal government. Mr. Olson became the assistant attorney general in charge of the Office of Legal Counsel, which offers legal advice to the president and the executive branch.
Mr. Olson worked on the White House’s behalf during the initial stages of the Iran-contra affair, Congress’s investigation into the illegal arms sales to Iran to support right-wing rebels in Nicaragua. He was also accused of committing perjury during a congressional investigation into the White House’s withholding of environmental records.
That investigation, which lasted five years and personally cost Mr. Olson $1.5 million, ended without charges. It made him a darling among conservative commentators, but left many Democrats convinced that he was dangerously partisan.
Mr. Olson resigned in 1984 and afterward helped expand his law firm’s Washington office. He built a reputation for promoting women within the firm at a time when few were in high-ranking positions.
He returned to the national political spotlight in 2000, when he led Republican efforts to block a ballot recount in several Florida counties narrowly won by George W. Bush. Mr. Olson argued the case up to the Supreme Court, where he — and his client, Mr. Bush — prevailed in December 2000.
A few months later, Mr. Bush repaid the favor by nominating Mr. Olson to be solicitor general, a job often seen as a holding pen for future attorneys general. The move set off a firestorm among Senate Democrats, who tried but failed to block the nomination.
Mr. Olson’s first two marriages, to Karen Beatie and Jolie Bales, ended in divorce.
His third wife, the conservative commentator Barbara (Bracher) Olson, was aboard American Airlines Flight 77 to Los Angeles from Washington on Sept. 11, 2001, when Al Qaeda terrorists hijacked it, crashing it into the Pentagon and killing everyone aboard.
She had planned to leave the day before, but had stayed an extra day to be with Mr. Olson on the morning of his birthday. As the plane veered back toward Northern Virginia, where they lived, she called him from a bathroom, and Mr. Olson was able to record some of the call. His telephone is now in the collection of the National Museum of American History.
In addition to his Mrs. Booth Olson, whom he married in 2006, Mr. Olson is survived by his children, Kenneth and Christine Olson; his brother, John; and his sisters, Claudia Alt, Kirstin Cravens and Joan Hushahn.
Mr. Olson resigned as solicitor general in 2004 and returned to work at his law firm. The next year, the Bush administration strongly considered him to replace Sandra Day O’Connor on the Supreme Court, and in 2007 to replace Alberto Gonzales as attorney general, but it backed off after Democrats said they would block the nominations.
Mr. Olson remained a committed Republican. He supported Rudolph Giuliani’s 2008 campaign for the Republican presidential nomination, and in 2012 he helped Representative Paul Ryan, Mitt Romney’s running mate, prepare for election year debates by playing Joseph R. Biden, who was then vice president, in practice sessions.
He also took up a number of high-profile cases in one of his many specialties, sports law — among them, defending the quarterback Tom Brady of the New England Patriots after he was penalized for illegally deflating balls during the 2015 A.F.C. championship game.
One client whom Mr. Olson refused to take on was President Donald J. Trump, when he was asked to join the White House legal team during Robert Mueller’s investigation into Russian interference in the 2016 election. Mr. Olson told MSNBC that taking the job would have been too risky.
“I think everybody would agree this is turmoil, it’s chaos, it’s confusion,” he said.
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