Students for a Democratic Society (SDS), the most radical student organization of the 1960s, held its first meeting in Ann Arbor, Michigan in 1960. Two years later SDS adopted as its manifesto the Port Huron Statement drafted by Tom Hayden, which identified poverty and civil rights as the group's primary concerns, and the Cold War and peace, issues that would later take on a more central role, as secondary concerns. The group's commitment to "participatory democracy" quickly catapulted them to the forefront of the New Left political movement, resulting in aggressive surveillance by the F.B.I. In fact, the bulk of this series consists of F.B.I. files documenting Oglesby's every move during his time with SDS and continuing for many years after. Individuals who associated themselves with the New Left, in particular members of SDS, were often accused of being Communists. Frequent trips to Cuba by SDS members, including Oglesby, did little to dispel this notion.

The bulk of this series is made up of copies of F.B.I. surveillance records tracing Oglesby's movements both during and after his term as SDS president. Also included are articles about SDS and the Weatherman by Oglesby and others, newspaper clippings, correspondence, interviews with former SDS people, speeches given by Oglesby, and notes.

An internationally recognized authority on the assassination of John F. Kennedy, Oglesby has written and lectured on the topic extensively. As a founding member of the Assassination Information Bureau (AIB) in 1972, he played a critical role in raising public awareness about the inconsistencies among eyewitness accounts, film evidence, and published reports of the assassintation, most notably in the findings of the Warren Commission released in 1964. After the Watergate scandal and Nixon's resignation in 1974, the AIB continued to demand the release of previously restricted documents, calling for the accountability of U.S. intelligence agencies. Indeed, the group is often credited with prompting the 1976 Congressional reinvestigation into the assassinations of Kennedy and Martin Luther King, Jr.

A large portion of the series consists of materials relating to the AIB, including correspondence, bibliographies, reports, and the group's newsletter, Clandestine America. Oglesby was one of a few AIB members to travel throughout the country as a part of the group's "Who Killed JFK?" program, which sought to inform the public, especially college students, of inaccuracies and inconsistencies found in published reports of the assassination. Documenting his involvement in this program are lecture scripts, notes, and publicity flyers promoting speaking engagements. Oglesby's typescript drafts and published articles are central to understanding the evolution of his thoughts about the assassination and its cover up. The various versions of articles and books included among these materials can be seen as culminating in the book proofs for Oglesby's 1992 work, Who Killed JFK?. Finally, his personal correspondence received after the December 1991 release of Oliver Stone's film JFK and the numerous articles by other authors submitted for his review illustrate Oglesby's central role in uncovering the truth about the JFK assassination.

In one of Oglesby's most widely known political theories, referred to as the "Yankee and Cowboy War," he depicts Northern, old money "Yankees" and Southern and Western, new money "Cowboys" in a struggle for power and dominance in post-World War II America. His book named for the theory traces the effects of this political struggle from the Bay of Pigs incident in 1961 to Watergate in 1973-1974.

In the book, Oglesby claims that the failure of the Bay of Pigs Invasion was the result of internal conflict in Washington, namely the shaky coalition between President John F. Kennedy (Yankee) and Vice President Lyndon B. Johnson (Cowboy). Oglesby further claims that this uneasy alliance between the North and South resulted in the escalation of the Vietnam War, as well as other foreign policy disasters that plagued the administration before and after Kennedy's death. Oglesby refers to the Vietnam War as a "Cowboy War," which ultimately resulted in such high level pressure from "top class Yankee gunslingers," such as Defense Secretary Clark Clifford, that Johnson was unable to seek re-election. He also examines events such as the suspicious Watergate plane crash that killed Dorothy Hunt, the wife of Watergate conspirator E. Howard Hunt, the possibility that James McCord, also a Watergate conspirator, was a double agent, the assassination of John F. Kennedy, and Howard Hughes' relationship with the United States government.

The series contains materials relating to Oglesby's book, such as drafts of the manuscript, research materials including articles and newspaper clippings, correspondence concerning its publication, and published reviews.

For more than three decades, Oglesby researched the Gehlen Organization and its role in post-World War II America. As the war came to a close, top-ranking Nazi officials scrambled to find a way out of Germany. One such official was Reinhard Gehlen, the head of the Former Armies East (FHO) in the German Army Headquarters, also known as the Gehlen Organization. This was an important branch of the Nazi intelligence system that oversaw all intelligence and military operations throughout Eastern Europe and the Soviet Union. This arm of Soviet intelligence was particularly powerful because of Gehlen's close association with and influence over Foreign Armies West and the Odessa. The Odessa was arguably the Nazi's greatest organizational achievement because it not only controlled the SS and Gestapo but also set up "rat lines" which allowed thousands of Nazi officials to escape Germany after the war.

The U.S. government, anxious to achieve a reliable intelligence network to spy on the Soviet Union, was not opposed to making a deal with Gehlen to acquire his West German intelligence network in exchange for allowing Nazis to quietly escape Germany after the war. The FHO, after all, was the only organization in the Third Reich that gained power and recruits even as the war was winding down. On August 24, 1945, one week after the Nazi's "unconditional surrender," Gehlen arrived in Washington D.C. to sell his organization to the United States and buy himself a way out of Germany.

The meeting in Fort Hunt, Virgina, ended with a "gentleman's agreement" to employ Gehlen as an official in the newly formed C.I.A., for which Gehlen worked until 1968. Gehlen himself spelled out the terms of this agreement in his book, The Service: The Memoirs of Reinhard Gehlen, which has come under intense criticism for being inaccurate. Nonetheless, according to Gehlen, "The Secret Treaty at Fort Hunt" essentially merged Nazi Gehlen Organization and U.S. intelligence with the understanding that although the Germans and Americans would be working "jointly," the United States would provide complete funding for all activities. Interestingly, according to Gehlen, it was also understood that should German and American interests come into conflict with each other, the Gehlen Organization would "consider Germany first." This conflict of interest presented itself almost immediately as the post-war hunt for Nazi war criminals began and tensions between the Soviet Union and the United States escalated.

Oglesby's interest in the Gehlen Organization ultimately resulted in a lawsuit against the federal government. In the suit (Carl Oglesby v. Department of the Army, et al), he claims the government refused to release documents that should be open to the public under the Freedom of Information Act. This lawsuit has been circulating through the court system for almost twenty years and has forced various governmental agencies to release thousands of pages of previously "classified" and "top secret" documents to Oglesby. Oglesby's counsel in this matter, James Lesar, specializes in litigation pertaining to the Freedom of Information Act, and has logged thousands of hours over the years fighting for the release of documents pertaining to World War II, the Gehlen Organization, and former Nazi government officials and military officers.

Numerous drafts of articles, book excerpts and lectures are included in this series, although it should be noted that Oglesby has yet to publish a complete book on this topic. An extensive article by Oglesby, "The Secret Treaty of Fort Hunt," was published in Prevailing Winds magazine. A considerable portion of his research materials are also included in this series. These consist of articles, newspaper clippings, book excerpts, correspondence, charts drawn by Oglesby explaining the complicated connections between the various government agencies and people, government reports, and intelligence documents obtained by Lesar under the Freedom of Information Act.

This subseries contains drafts and research material for Oglesby's memoir, "Ravens on the Wing." In it he covers, in detail, the move away from his middle class life as a technical copy editor in the defense industry, his experiences as president of SDS, which include his relationship with Weatherman founder Bernadine Dohrn, trips to Cuba and North Vietnam, and his travels around the country giving speeches for SDS. He also discusses the painful period when the Weatherman split from SDS and his own experiences with SDS after.

Included in this subseries are numerous drafts of the memoir, published in 2008 as Ravens in the Storm. Also included is correspondence concerning the book, newspaper clippings, articles, writing fragments, notes, and some photographs from Oglesby's trip to Cuba.

This series, more than any other, chronicles Oglesby prodigious writing career. He has written extensively on SDS, the New Left, the JFK assassination, Vietnam, Watergate, and his theory of the Yankee-Cowboy war. Although the bulk of Oglesby's writing is political in nature, he has written about many things that range from discussions of the New Left, the war in Vietnam, critiques of teach-ins, literature, Cuba, Boston public transit, Boston University, genetic engineering, farms in America and many verses of unpublished poetry. Also included in this subseries is correspondence with people like Noam Chomsky, academic papers from Oglesby's undergraduate career and Oglesby's 1965 paper, "The Vietnam War: World Revolution and American Containment," which ultimately became the SDS position paper for the Vietnam War.

Although Oglesby has not written as extensively on religion, he has maintained his interest in it over the years, publishing two articles on the subject, "Rescuing Jesus from the Cross" (1983) and "Art at the Apocalypse" (1982). His unpublished manuscript "The Sermons of Judas" is also included along with research materials relating to this manuscript and other religious items such as church programs, flyers, and eulogies.

Oglesby's personal correspondence with various family members, business associates, and friends, as well as documents relating to his publishing contracts, photographs, announcements, invitations, and various printed materials and newspaper clippings. Also contains materials relating to Oglesby's work with the Center for Strategic and International Studies.

Both as president of SDS and later as a founder of the Assassination Information Bureau, Oglesby traveled around the country meeting people and giving talks. His 1966 lecture at Antioch College is included here as are the numerous slides he used when delivering his presentations on the assassination of Kennedy. Oglesby used audio and video recordings as part of his own research, compiling a collection of documentary's on the JFK assassination and Reinhard Gehlen and the Nazi connection to U.S. intelligence agencies.