Robert James Woolsey Jr. (September 21, 1941 – July 21, 2026) was an American lawyer who served in various senior government positions. He headed the Central Intelligence Agency (CIA) as Director of Central Intelligence from February 5, 1993, until January 10, 1995. He held a variety of government positions in the 1970s and 1980s, including as United States Under Secretary of the Navy from 1977 to 1979, and was involved in treaty negotiations with the Soviet Union for five years in the 1980s. His career also included time as a professional lawyer, venture capitalist, and investor in the private sector.
Woolsey was born in Tulsa, Oklahoma on September 21, 1941, the son of Clyde (Kirby) and Robert James Woolsey Sr. He graduated from Tulsa's Tulsa Central High School. In 1963, he received his Bachelor of Arts from Stanford University with high honors and membership in Phi Beta Kappa, then was awarded a Rhodes Scholarship to study in England at St John's College, Oxford, where he earned a Master of Arts degree, graduating in 1965. In 1968, he received his Bachelor of Laws from Yale Law School.
Woolsey held important positions in both Democratic and Republican administrations. His influence was felt during the administrations of Jimmy Carter, Ronald Reagan, George H. W. Bush, and Bill Clinton. He also worked at the Shea & Gardner law firm, as Associate (1973–1977) and partner (1979–1989, 1991–1993).
He served in the U.S. government as:
Advisor (during military service) on the U.S. delegation to the Strategic Arms Limitation Talks (SALT 1), Helsinki and Vienna, 1969–1970
General Counsel to the U.S. Senate Committee on Armed Services, 1970–1973
Under Secretary of the Navy, 1977–1979
Delegate at Large to the U.S.-Soviet Strategic Arms Reduction Talks (START) and Nuclear and Space Arms Talks (NST), Geneva, 1983–1986
Ambassador to the Negotiation on Conventional Armed Forces in Europe (CFE), Vienna, 1989–1991
Relationship with Bill Clinton
As Director of the CIA, Woolsey had limited access to President Bill Clinton.
A quote about his relationship with Clinton, according to Paula Kaufman of Insight on the News:
Remember the guy who in 1994 crashed his plane onto the White House lawn? That was me trying to get an appointment to see President Clinton.
David Halberstam notes in War in a Time of Peace that Clinton chose Woolsey for CIA director because the Clinton campaign had courted neoconservatives leading up to the 1992 election, promising to assist democratic Taiwan, Bosnia in the Bosnian War, and be tougher on human rights violations in the People's Republic of China, and it was decided that he ought to give at least one neoconservative a job in the administration.
Woolsey was CIA director when Aldrich Ames was arrested, on February 21, 1994, for treason and spying against the United States. The CIA was criticized for not focusing on Ames sooner, given the obvious increase in Ames's standard of living; and there was a "huge uproar" in Congress when Woolsey decided that no one in the CIA would be dismissed or demoted at the agency. Woolsey declared: "Some have clamored for heads to roll in order that we could say that heads have rolled ... Sorry, that's not my way." Woolsey abruptly resigned on December 28, 1994.
Woolsey joined the board of directors for The Arlington Institute in 1992.
He was at the time of his death a member of the Washington Institute for Near East Policy (WINEP) Board of Advisors, Advisor of the Institute for the Analysis of Global Security, co-founder of the United States Energy Security Council, Founding Member of the Set America Free Coalition, and a senior vice-president at Booz Allen Hamilton for Global Strategic Security (from July 15, 2002).
Woolsey was a Patron of the Henry Jackson Society, a British think tank. Woolsey had long-standing contact with Central and Eastern Europe and as a Member of the Board of Advisors for America of the Global Panel Foundation based in Berlin, Copenhagen, Prague, Sydney, and Toronto. He was a past chairman of the Freedom House board of trustees. He was a member of the International Advisory Board of NGO Monitor.