Yale Daily News

The first glimpse of Yale in Robert DeNiro’s “The Good Shepherd” is nothing like the traditional image of the stuffy Ivy League of the early 20th century: Matt Damon — playing Edward Wilson, a fictional Yale student — stands on a stage in full makeup and drag, singing a Gilbert and Sullivan tune in exaggerated falsetto, as a well-dressed audience chuckles appreciatively.

But when a group of somber men in suits approaches Wilson backstage and taps him for Skull and Bones, the film quickly enters into territory familiar to most Yalies as well as many American moviegoers who have heard the legends and myths about the infamous society. Wilson’s invitation into what one Bonesman in the film calls “America’s most select secret society” sets him on the path to becoming one of the founding members of the Central Intelligence Agency.

Although Edward Wilson never existed, the character is based on the real Yale graduate James Jesus Angleton ’41, who was a counterintelligence expert for the CIA. In general, Yale played a very important role in the development of American espionage, said Gaddis Smith ’54 GRD ’61, professor emeritus of history, and many Yale graduates went on to hold powerful positions in both the CIA and the Office of Strategic Services, the precursor to the CIA. But Smith emphasized that much of “The Good Shepherd,” including its depiction of Yale in the 1930s, bears little resemblance to reality.

“There certainly was an enormous movement of Yale students into the OSS and the CIA,” Smith said. “[But] it was fiction — it was someone’s imagination of Yale.”

According to the book “Cloak and Gown” by the late Yale history professor Robin Winks, Yale’s connections with the CIA run deep. In the class of 1943 alone, at least 42 members entered intelligence work after graduation, and Winks writes that the OSS was so heavily populated with Yale graduates that members stationed in remote areas of Asia and Africa during World War II — Yalies and non-Yalies alike — would frequently end “a festive occasion” with a round of the Whiffenpoof Song.

The CIA, and the OSS before it, employed a disproportionate number of students from a few elite universities — not only graduates of Yale, but also of schools like Harvard, Princeton and Brown. Smith said this elitism, as well as a widespread idealism about the United States’ role in the fight against fascism and communism, contributed to Yale’s strong history with the CIA. In fact, he said, “The Good Shepherd” could have done a better job of conveying the extent to which the agency, like Yale itself, was a bastion of wealth and social power in the early and middle parts of the century.

“It was very much an Ivy League operation,” Smith said. “It was kind of an elite club of often very wealthy people, but also people who were … in the social register.”

Several Yale faculty members also held significant positions in espionage, including Sherman Kent, history professor and a founder of the CIA, and Norman Holmes Pearson, an English professor who recruited for the agency and who Smith said may have inspired the character of the professor played by Michael Gambon in “The Good Shepherd.”

Richard Bissell, Jr. ’32, a one-time member of the Yale Economics Department and the Director for Plans for the CIA in the late 1950s and early ’60s, played a leading role in planning the failed Bay of Pigs invasion, and may have partially inspired the Wilson character in the movie, Smith said.

But Wilson’s character was largely modeled on Angleton, one of the best-known and most influential of the many Yalies who went into espionage. Winks writes in “Cloak and Gown” that while Angleton — who would become one of the world’s leading experts in the methodology of counterintelligence — was a legendary figure in the CIA, he was not a particularly good student while at Yale and only did well in subjects that interested him.

Tom Mangold, author of “Cold Warrior,” a book about Angleton that is mentioned in the credits of “The Good Shepherd,” said while he has not yet seen the movie, he met with Damon before filming to discuss the aspects of the Edward Wilson character that were influenced by Angleton. But the movie’s depiction of Wilson’s life seems to bear little resemblance to Angleton’s, Mangold said — for instance, while Wilson was a central part of the Bay of Pigs invasion, there is no evidence that Angleton had any involvement in the disaster.

There are some parallels, however. Like his fictional counterpart, Angleton was a member of Skull and Bones, where Mangold said he made a number of connections that served him well throughout his career.

“I think he loved secret work, and don’t get me wrong on this, but he loved the power of secrecy,” he said. “Any secret society would have appealed to Jim enormously.”

Smith said the film took extensive liberties in its portrayal of Skull and Bones. For example, Smith said, the portrayal of the elaborate initiation ceremony that Wilson undergoes was “really over the top,” although the exaggeration reflects a general public fascination with the influential society.

Secret societies, and Skull and Bones in particular, have an aura of mystery that makes them popular fodder for the media, said Alexandra Robbins ’98, author of the book “Secrets of the Tomb,” about Skull and Bones.

“The society sends out a lot of smoke and mirrors, and deep down people like to believe in conspiracies, and they like to believe that secret societies are more powerful than they actually are,” she said.

Still, while the depiction of Skull and Bones in “The Good Shepherd” caters to an audience familiar with the conspiracy theories, Robbins said, Bones’ ties with the CIA are legitimate. She recalled an interview with one member of the society who said many Bonesmen viewed the agency as an “employer of last resort.”

Although members of Skull and Bones closely guard access to the actual tomb, Smith said he thought the depiction in “The Good Shepherd” of a soaring circular hall supported by massive columns was “very largely the act of a creative imagination.” In “Secrets of the Tomb,” Robbins describes the real-life interior as resembling “the Victorian house of a pack rat.”

The scenes in the movie meant to represent Yale were actually filmed at schools around New York, including Brooklyn Community College and the Pratt Institute. Donald Filer, associate secretary for the University, said a location scout for “The Good Shepherd” made contact with Yale officials in 2004 to discuss shooting scenes for the film on campus, but that the filmmakers ultimately decided not to shoot in New Haven. Filer said that it is generally cheaper to film as much of a movie as possible in one place, and speculated that “The Good Shepherd” was filmed mostly in New York because of cost issues.

Students who saw the film had mixed reactions to the portrayal of the University. Some said they thought it did a good job of capturing the spirit of what Yale might have been like in the 1930s, while others said they found the movie confusing or overlong. Most said they liked seeing their school on the big screen, even though it did not bear much resemblance to the real-life campus.

Joe Kye ’09 said he thought “The Good Shepherd” was well-acted and featured good character development, but its references to Yale were almost comically misinformed. He said he found the scene where members of Skull and Bones stand around singing the Whiffenpoof song particularly ridiculous.

“There were parts in the movie where I kind of laughed out loud because of the way they chose to portray Yale,” Kye said. “People will watch the movie now, and — although they know logically in their heads that this movie is tying to portray the 1930s — they’re still going to see it and equate Yale with this pompous, pretentious white college.”

But Mimi Lewis ’09 said, while she did not fully understand the plot of the movie, she enjoyed it in part because of the important role Yale played in the story.

“Since I saw it [in New Haven], I felt like it belonged to all of us,” she said. “I liked that we’re part of this Yale tradition that’s so famous.”