Former CIA Director James Woolsey, Who Served Under Clinton and Later Advised Trump, Dies at 84

James Woolsey, who headed the Central Intelligence Agency under Bill Clinton’s administration, died Tuesday at the age of 84.

According to The New York Times, Woolsey died at his home in Washington, D.C., of a stroke.

“CIA extends our condolences to the family and loved ones of former Director James Woolsey,” the CIA said in a statement Wednesday afternoon.

“He was a great patriot who served his country as Director of Central Intelligence, Undersecretary of the Navy, Ambassador, and attorney.”

CIA extends our condolences to the family and loved ones of former Director James Woolsey. He was a great patriot who served his country as Director of Central Intelligence, Undersecretary of the Navy, Ambassador, and attorney. pic.twitter.com/v9u93ooC41

— CIA (@CIA) July 22, 2026

Born Robert James Woolsey in Oklahoma in 1941, Woolsey attended Stanford University and later won a Rhodes Scholarship to Oxford. After obtaining his master’s degree there, he headed to Yale Law, graduating in 1968.

According to The Hill, his first job in federal government was at the National Security Council in 1970.

Woolsey served several administrations in various positions before being promoted to the head of the CIA in the early years of the Clinton administration; Clinton reportedly viewed his hawkishness as a way to mollify congressional Republicans who were skeptical of his bona fides on defense.

While the relationship wasn’t frosty, it also wasn’t close. The best summation of the relationship possibly came from Richard Minter in his book “Losing bin Laden: How Bill Clinton’s Failures Unleashed Global Terror.”

“When a small plane accidentally crashed into the White House lawn in 1994, West Wing staffers joked that it was [Jim] Woolsey trying to see the president,” Minter wrote.

Woolsey also had a rocky tenure, with two terror attacks in his first year — including the first World Trade Center attack, a truck bombing — as well as dealing with the fallout from the collapse of the Soviet Union.

The breaking point for Woolsey’s support in Washington arguably came with the arrest of spy Aldrich Ames, which the CIA director called a “systemic failure” at the agency.

However, no one faced dismissal or even demotion for those failures, which led to further erosion of the director’s support base. Woolsey subsequently submitted his resignation in December of 1994.

Woolsey would subsequently turn rightward in his political inclinations. He supported George W. Bush’s invasions of Afghanistan and Iraq, preemptively making the case for invasion of the latter during a television appearance in 2003.

“I don’t know how many pieces of evidence one needs in the case of someone like Saddam Hussein. We know Saddam is working hard on weapons of mass destruction,” he said, adding that Hussein “put a lot of time and effort in on biological weapons programs, as well as ballistic missile programs and nuclear programs. We know that he guarded more jealously than anything the details of his biological weapons programs.”

Woolsey would later admit this was faulty intelligence.

In 2016, Woolsey became a senior adviser to Donald Trump’s first presidential campaign, something the Times said “was driven by the candidate’s advocacy for growing the defense budget and harsh critique of the Obama administration’s nuclear deal with Iran.”

Woolsey, who was married three times, is survived by his current wife, three children, and five stepchildren.

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