From the New JFK Files, the Untold Story of Angleton and Oswald

Nine documents about the legendary counterintelligence chief James Angleton expose his 'deeply deceptive' actions concerning the patsy/assassin

Left: Colorized photo of Lee Harvey Oswald in a Moscow hotel room in October or November 1959 (Credit: Warren Commission). Right: Colorized photo of CIA counterintelligence chief James Angleton in 1976 (Credit: Richard Avedon).

The latest of the JFK assassination files, released by President Donald Trump last week, yielded 13 newly declassified documents about CIA counterintelligence chief James Angleton. These long-secret records, along with others released with less fanfare in recent years, implicate the legendary spymaster more deeply in the intelligence failure represented by the murder of President John F. Kennedy on Nov. 22, 1963.

These unexpurgated FBI and CIA memoranda complicate the comforting narrative that the liberal president was killed by a “lone nut” who murdered for reasons known only to himself and denied committing the crime, supposedly because he was guilty of it.

The new JFK files tell a different story. They show that Lee Harvey Oswald, far from being an isolated sociopath, was a figure of abiding covert interest to one of the top men in the CIA for four years before Kennedy died in a hail of gunfire in Dallas.

That man was James Jesus Angleton.

Legend of a Spy

Over the decades, Angleton has come to represent an archetypal American spy, alternately brilliant, paranoid, foolish, and sinister. He was the hero of William F. Buckley’s entertaining yarn “Spytime.” In Norman Mailer’s more serious CIA novel “Harlot’s Ghost,” he was the title character, Hugh Tremont Montague.

In Robert De Niro’s big screen saga, “The Good Shepherd,” Angleton became Edward Wilson, a spy born of corrupted idealism. Most recently, he flitted through the small screen of the Apple TV series, “A Spy of Among Friends,” as just another dupe of Soviet spy Kim Philby.

Fictions aside, in reality Angleton was a clever and dangerous man, and he sometimes looked the part. “Like his ectoplasm had run out,” quipped CIA man David Phillips. One CIA station wife who knew him well over many years told me Angleton was an ominous and untrustworthy man. She hated his influence over her husband.

Others admired the power of his intellect and deeds. Efraim Halevy, former director of Mossad, told me Angleton could only be judged a world historic figure. In the estimation of CIA director Richard Helms, he was a master of the secret intelligence profession.

“Jim had the ability to raise an operational discussion not only to a higher level,” Helms marveled, “but to another dimension.”

James Angleton, retired CIA spymaster, testified to Congress in 1975 and again in 1978.

Targeting Oswald

As reported by Fox News analyst James Robenalt, the new JFK files illuminate an unknown but unfolding chapter in Angleton’s extraordinary career: his abiding interest in Kennedy’s supposed killer Oswald long before Nov. 22, 1963.

In July 2023, Peter Baker of the New York Times reported that a newly released JFK document showed that a CIA officer named Reuben Efron, working for Angleton, was reading Oswald’s mail during JFK’s presidency. More details of this intriguing story emerged last week.

• One 1958 FBI memo, not declassified until last week, indicates that Angleton put Oswald under mail surveillance in 1959 for possible approach as a CIA “contact” or “source.”

• The declassified transcript of Angleton’s closed-door testimony to Senate investigators in June 1975 shows how Angleton exploited his Israeli connections to build his intelligence empire in Washington at the same time his staff was monitoring Oswald.

• A third JFK document — declassified in 2023 and reported here for the first time — reveals that Angleton lied under oath to the House Select Committee on Assassinations (HSCA) in 1978.

The story of Angleton’s four-year surveillance of Oswald and his stonewalling of investigators emerges with new clarity from last week’s document dump. It is now clear why these details have been kept secret for 60-plus years: because they fill out a new and disturbing fact pattern of CIA malfeasance around JFK’s assassination.

Polarization and History

Public understanding is, inevitably and unfortunately, bifurcated by the polarization of media discourse. While conservative platforms are eager to challenge the conventional lone gunman narrative in support of President Trump’s campaign against “the deep state,” liberal pundits assume the new files will give no comfort to the “conspiracy theorists” whose irrationality defaces our politics.

(As a JFK historian, I find it curious that I get twice as many queries from right/conservative outlets as from liberal/left—about the assassination of a liberal hero.)

Partisan politics aside, the new JFK files certainly confirm what has become undeniable in recent years: Kennedy’s supposed killer was a person of interest to one of the top men at the CIA in the years, months and weeks before Kennedy was killed on Nov. 22, 1963.

The new JFK files also show that after JFK was dead, Angleton concealed his knowledge of JFK’s putative killer from the rest of the CIA and from two assassination investigations.

“Angleton’s actions over many years were deeply deceptive," Professor Larry J. Sabato, director of the Center for Politics at the University of Virginia and author of "The Kennedy Half Century,” told me in an email. "It’s clear he placed protecting the CIA over telling the truth about the CIA’s actual knowledge of, or relationship with, Oswald.”

NEXT: Three Revelations about Angleton, the CIA, and JFK