Nathan Hale, a Revolutionary War hero & graduate of Yale, was hung as a spy by the British. From the first steps of our country, spying, intelligence, and the Ivy Leagues have been very connected.
From its birth during WWII, the OSS (and later the CIA ) has been filled from the ranks of the Ivy Leagues (especially Yale). William J. "Wild Bill" Donovan, the founder and director of the OSS, was a Columbia educated lawyer. He recruited from those graduating or still at Yale, Harvard, Columbia, & Princeton.
In his book 'Cloak & Gown,' Robin Winks wrote that at one point the unofficial song of the OSS was the Whiffenpoof Song (see below) - a song heard on the campus of Yale since 1909 - and could be heard in the hillsides and forests of England, France, Germany, & later, Burma & China. ″There were at least 42 members of the class of 1943 alone, for example,″ he said. About 30 faculty members on leave and a ″goodly number″ of doctoral students, worked on intelligence that year, Winks said.
Norman Holmes Pearson, a Yale professor pre-war, worked during World War II as the director of counterintelligence for the OSS in London. He helped form the CIA post-war and recommended his no.2 James Jesus Angleton as CI Chief. He went on to form the American Studies department at Yale which was critical in promoting the American story & national interest and recruiting CIA, DIA, and other agents domestically, as well as turning foreign nationals into intelligence assets.
Through the years, other 'Yalies' have been a big part of CIA from one-time director George H.W. Bush (also a Skull & Bones secret society member) and James Jesus Angleton, the once CI chief of the CIA during the a most intense portion of the 'spy wars' during the Cold War.
Bush served as CIA director under President Gerald Ford as the Agency was emerging from what could’ve been the ‘death knell’ after the leak of the Family Jewels. The Family Jewels was a compiling of secret activity the Agency had taken part in (both legal and illegal) that was leaked to the press under Director James Schlesinger. Bush helped to steer the Agency back to its roots and provide a layer of transparency and trust to Congress. According to the CIA website, he is known to this day as one of the most beloved Directors and is credited with saving the CIA in the 1970s.
James Jesus Angleton, who served as Chief of Counterintelligence from 1954 to 1974. Angleton was known as an uncompromising CI Chief and obsessed with hunting down moles within the Agency & government. From accusing sitting Heads of State of West Germany & Canada of working for the Soviet Union to ordering domestic surveillance on anti-war and suspected communist sympathizers, Angleton has a checkered view in intelligence history. He is still viewed highly within the Agency for his voracious tracking of KGB infiltration. In 1974, he was asked to resign by other Ivy Leaguer Bill Colby.
Along with Donovan & Bush, there have been a few more Ivy League educated directors including Allen Dulles (Princeton '16), James Schlesinger (Harvard '50), William Colby (Princeton '40), and Porter Goss (Yale '60).
Dulles is known as the father of the modern CIA and is still highly revered within its halls. His brother, John Foster Dulles, served as Secretary of State under President Eisenhower, and along with Allen, was a staunch advocate of aggression against the Soviet Union and its expanding brand of communism. Dulles was another OSS veteran and close ally of Donovan. Dulles is known for increased action taken against communism including the failed Bay of Pigs invasion and coups in Iran and Guatemala. He was asked to resign by President Kennedy in 1961.
James Schlesinger served as DCI under Nixon for around 5 months and was universally disliked within the Agency. He was seen as a Nixon loyalist who increased tensions between the Agency and the Executive branch. He was succeeded by another Ivy director in William “Bill” Colby.
Colby had served under Donovan in the OSS during WWII including time as a Jedburgh commando, and later graduated Columbia and joined Donovan’s law firm after the war. He quickly rejoined the CIA by an invitation from an old OSS friend and served in the field for 12 years. This included time helping to build the Gladio Network, a stay behind guerrilla force to counter the Soviets in case of an invasion in Sweden. He then spent time in Indochina, including Vietnam, and helped form the Phoenix Program. This controversial program was used to identify and neutralize Viet Cong infrastructure, leadership, and influence, up to and including, targeted assassinations and kidnapping. Colby returned to the States and assumed a leadership role in the CIA helping to lead it in reform of budget and action started by Schlesinger. Colby resigned in 1975 and was replaced by George H.W. Bush (covered above).
Finally, Porter Goss is the most recent Ivy League DCI to grace the halls of Langley. Goss was appointed by President George W. Bush in 2004 in the midst of the intelligence failures that led to the Iraq War and following the 9/11 attacks in 2001. Goss, having served previously as chairman of the joint House committee on intelligence, had ties to the Agency. Goss pushed for less risk aversion in intelligence gathering and aimed to shake up the status quo that had settled in the CIA post-9/11. Goss served until 2005 as DCI and then served as the first Director of the CIA after the formation of the Director of National Intelligence in 2006.
While the CIA, has worked hard to diversify over the last few decades, the Ivy Leagues are still fertile ground for the next generation of intelligence collecting (and still the home of the preppy lifestyle). A walk through its halls is filled with Yalies, Harvard Men (and women), and men & women from Princeton, Brown, & Columbia. You will also find an increasing number of state school graduates, HBCU alum, and the members from the ‘Military Ivies’: West Point (USMA), Annapolis (USNA), and Colorado Springs (AFA). All that means, in some ways, less preppy but it shows a commitment amongst our nation to have viewpoints that are both varied and diverse, which is a win, at least, for this Preppy Statesman.