Theodore B. Olson, Esq.

Theodore Olson – Oral History Summary

by Eva Petko Esber

To the best of his recollection, Theodore Olson never even met a lawyer until his senior year of college.  But two influential mentors helped set Olson’s course toward partnership in a prominent law firm, as well as positions in the administrations of Presidents Ronald Reagan and George W. Bush.  In that legal career of almost sixty years, Olson presented more than sixty oral arguments to the United States Supreme Court, both as 42^nd Solicitor General of the United States under President Bush, and in his private practice at Gibson Dunn.

In an oral history taken by the Historical Society of the District of Columbia Circuit, Olson shares recollections of the people and experiences that most profoundly influenced him. The oral history consists of seven sessions convened between October 2013 and December 2020.  The interviews were conducted on behalf of the Historical Society by Elizabeth Beske, Professor of Law at American University Washington College of Law.  They discuss at length Olson’s involvement in some of the most prominent and controversial cases decided by the United States Supreme Court in the late Twentieth and early Twenty-First Centuries.  These include, most notably, the Supreme Court’s decision in 2000 in Bush v. Gore, which stopped the recount of votes in Florida on Equal Protection grounds, and secured the presidency for George W. Bush.  They also include his successful championing of the appellants’ position in the Supreme Court’s 2010 decision in Citizens United v. Federal Election Commission, which reversed long-standing campaign finance restrictions, and recognized a first amendment right of corporations and other groups to spend unlimited funds on election issues.  Those cases, among many others, seemingly cemented Olson’s legacy as a prominent Republican advocating conservative causes.   But Olson complicated that labelling.  He successfully advocated for the right of same-sex marriage in California, a lengthy litigation that culminated in the 2013 Supreme Court decision, Hollingsworth v. Perry, which found that the proponents of Proposition 8 (banning same sex marriage in California) did not have standing to appeal the District Court’s holding that overturned Proposition 8.  Likewise, in the Supreme Court’s 2020 decision in U.S. Department of Homeland Security v. Regents of the University of California, Olson was successful in challenging the Trump Administration’s rescission of the Deferred Action for Childhood Arrivals (DACA) Program, generally known as the “Dreamers” Program.

Olson was born in 1940, and grew up in the San Francisco Bay area, the oldest of five children.  The family’s roots, however, were in Door County, Wisconsin.  As a child, Olson’s summers were spent in Wisconsin at his maternal grandparents’ cherry orchard and dairy farm, and at his paternal grandparents’ general store.  Olson’s father was an engineer with United Airlines.  After raising her children, his mother earned a Master’s Degree in Literature, and taught at a community college.  She instilled in Olson a love of learning, reading, and writing.  But at looking back for other early influences, Olson recalls, “[I]n our neighborhood there were no lawyers and nobody at my father’s work were lawyers.”

Olson entered college in the late 1950s as a Math major at the University of the Pacific, in Stockton, California.  There, the debate coach quickly altered Olson’s trajectory.  Olson recalls that coach, Paul Winters, as a “superb and inspirational teacher,” “one of those people who comes along very rarely.”  Despite being a relatively small school, the debate team successfully competed at the highest levels of collegiate debate.  Winters’ trained the team in a range of skills, from oratory to extemporaneous speaking, and from interpretive reading to salesmanship.   Inspired by Winters, Olson changed his major from Math to a double major in Speech and History.  Augmenting the debate team training, he took academic courses with Winters on subjects such as “Argumentation.”

Given his immersion in oral advocacy at college, it was not surprising that Olson went on to law school.  He enrolled in 1962 at Boalt Hall, at the University of California at Berkley. Still, he shares in the oral history, “I thought I wanted to be a tax lawyer because I was very challenged by the tax courses and problems in law school.”  In 1965, however, he joined Gibson Dunn’s Los Angeles office.  There, he soon came under the influence of another transformational mentor, William French Smith, and tax was left behind for litigation and politics.

In addition to being a partner at Gibson Dunn, William French Smith was involved with a group of prominent California Republicans.  That group was anxious to foster the political potential of Ronald Reagan, then a former actor and former President of the Screen Actors Guild.  Olson had dabbled in Young Republican activities during law school, but they were fully eclipsed by the high-profile progressive activists at Berkeley:  “That was 1964 or 1965.  There was the Lyndon Johnson, Barry Goldwater election in 1964, and our little group was supporting Goldwater, but no one really cared in Berkeley.  No one took any of us seriously.”  But what appealed to him about Goldwater, Olson shares, was “limited government, individual liberty, the antithesis of the Great Society.”  Once at Gibson Dunn, Olson quickly approached Smith about becoming involved in his political activities.  Smith, in turn, quickly deployed Olson to give speeches in his stead.  With just two-day’s notice, Olson recalls, he delivered his first speech on the issue of campaign finance after hurriedly researching the issues from scratch.

As the Gibson Dunn firm began doing legal work for the Reagans, Olson played his role too. “I wound up doing odds and ends, litigation-type stuff when one of the kids would get in trouble, or one issue here, or some issue there, I would do it.  And Bill [Smith] trusted me, and the Reagans trusted me.  So that’s sort of how that evolved. “  When Reagan became a two-term governor of California in 1967, Olson was appointed to the California Commission on Uniform State Laws, which Olson found fascinating, even though apolitical.  But more than a decade later, when Reagan became President in 1981, and William French Smith became Attorney General of the United States, Olson also came to Washington as the Assistant Attorney General for the Office of Legal Counsel, advising the White House and Executive Branch.

Although Olson’s appointment at the Department of Justice brought him into proximity with power, it also brought controversy.  Olson came under investigation by Independent Counsel Alexia Morrison on allegations of giving false and misleading testimony to Congress.  The allegations related to congressional investigations of, and subpoenas to, the Environmental Protection Agency, and Olson’s March 1983 testimony regarding the assertion of Executive Privilege and production of documents.  A Congressional committee issued a report that Olson had given false testimony.  After an Independent Counsel was appointed to consider charges, Olson, as the named litigant, challenged the constitutionality of the Independent Counsel statute as violating principles of separation of powers.  The Supreme Court’s 1988 decision in Morrison v. Olson rejected that challenge to the statute in a 7-1 decision, authored by Chief Justice Rehnquist.  The Independent Counsel thereafter issued a report critical of Olson as not being forthcoming, but did not bring charges.  The oral history includes Olson’s disappointment with the Court’s opinion in Morrison.  He shares his criticism of the Independent Counsel statute, generally summarizing its effect as creating an ”overwhelming impetus to prosecute.”  He also openly conveys the tremendous stress, anxiety and distraction he felt through the five-year investigation, which extended beyond his time as Assistant Attorney General.

Olson acknowledges in the oral history that his experience under an Independent Counsel investigation tempered his desire to return to government service after he resigned his position as Assistant Attorney General in 1984.  In the years that followed, he was building a very successful practice at Gibson Dunn.   But in 2000, the Republicans tapped him to lead the lead the federal litigation relating to the Florida re-count of votes in the Presidential election between George W. Bush and Al Gore.  After success in Bush v. Gore, Olson accepted the nomination of President George W. Bush to be Solicitor General.  Solicitor General, Olson says in the oral history, was the only position in the administration that interested him.  Aside from the opportunity to argue before the Supreme Court, he was impressed with the rich tradition of the office, and its talented lawyers.  Also important was that the Independent Counsel statute had lapsed, and he did not expect the post of Solicitor would involve testifying before Congress.  He served from 2001 to 2004.  He then returned again to Gibson Dunn for the remainder of his career, remaining a frequent advocate before the Supreme Court.

The very outset of Olson’s tenure as Solicitor General, however, tragically coincided with staggering personal loss.  His then-wife, Barbara Kay Olson, was among the passengers killed by terrorists on September 11, 2001 when American Airlines Flight 77 crashed into the Pentagon. At the time of her death, Barbara was a popular, successful conservative political commentator.  Her notoriety highlighted Barbara’s fate in the public eye, as did her efforts in placing two phone calls to Olson from the plane as the high-jacking was underway, alerting him to the situation on the fated flight. Olson readily acknowledges in the oral history that he sought refuge from his grief in his work.  He returned to office in a matter of days, and argued his first case as Solicitor General before the Supreme Court just three weeks after the terrorist attacks.  Olson also recognizes, however, the tremendous support he received from friends and family.  Eventually, through friends, he was introduced to Lady Booth, an attorney from Lexington, Kentucky.  The couple married in 2006.

Throughout the oral history, Olson discusses at length the important procedural, substantive and strategic issues of his most significant cases, as well as the controversy and legacy of those cases.   In the discussion of Bush v. Gore, for example, Olson resists contentions that it ushered in an era of litigating election results, particularly after the 2020 Presidential election.  As to the Citizens United campaign finance decision, Olson acknowledges, “I have been on program after program after program, and people will say this is the worst decision in the history of the United States Supreme Court, they forget about Dred Scott or anything else.”  Olson offers both understanding of the depth of feeling on the issues, as well as defense of the decision.  With respect to the Hollingsworth same-sex marriage litigation, Olson discusses the importance of evolving public opinion on same-sex  marriage.  In that case, he paired as co-counsel with David Boies, who was his opposing counsel from Bush v. Gore.  The seemingly unlikely pairing, it was hoped, conveyed that same-sex marriage was not a partisan issue.  As to the Regents of the University of California, the 2020 DACA argument, Olson discusses the significance of having Luis Cortes admitted to the Supreme Court the day of the argument, the first Dreamer admitted to practice before the Court.  Summarizing the considerations that extend beyond the legal analysis, Olson harked back to his college training with Paul Winters.  Olson emphasized, “When I was a college student, we thought of ethos, logos, and pathos. So, an argument has to have logic on its side, it has to have emotional appeal on your side.”

Theodore Olson passed away on November 13, 2024, at the age of 84.