This oral history interview with Otto Skopil was conducted by Rick Harmon and Jim Strassmaier in Skopil's chambers at the Pioneer Courthouse in Portland, Oregon, from August 19, 1985, to November 27, 1989. The audio for this interview is incomplete; Tape 26 was discovered to be blank in 2020, but its contents are reflected in an incomplete transcript and in an index.

In the interview, Skopil discusses his family background and early life in Salem, Oregon, including his time at Salem High School and the effect of the Depression and the New Deal on the Salem area. Skopil talks about attending Willamette University in great detail. He discusses his World War II experience in the Navy from 1942 to 1945, between earning his bachelor's degree in economics and returning to Willamette earn his bachelor of laws. Skopil describes practicing law in Salem for 26 years, from 1946 to 1972, including partnering with his uncle, Ralph Skopil, and later with Bruce Williams. He discusses some of the cases he argued, particularly his only U.S. Supreme Court case, which involved State Farm Insurance. He then briefly discusses his personal life, including his two marriages, first to June Johnson, then to Jan Lundy, and his involvement in various religious and civic organizations, including the Board of Governors for the Oregon Bar. He also discusses his involvement with the Republican Party and his opposition to both the Korean and Vietnam wars, as well as how the draft affected his son, Ric Skopil. He talks about serving as a judge for the U.S. Circuit Court of Oregon, including his confirmation; the procedures of the court; sentencing; and the development of the magistrate system. He also discusses some of the cases he presided over on topics including the environment, white-collar crime, and securities. He talks at length about the case of Chuck Armsbury. He also discusses working with his fellow judges, particularly Gus Solomon and Robert Belloni, as well as his relationships with Mark Hatfield and Griffin Bell. Skopil then describes his time as a judge for the Ninth Circuit Court of Appeals, including the relationship between that court and Congress; the increase of litigation during the 1980s; and the public perception of the court. He discusses some of the cases that came before the court on topics including mental health, capital punishment, timber, and drugs. He also talks about some of his fellow judges, particularly Ted Goodwin and James Browning. Skopil closes the interview by describing the importance of law clerks; discussing sentencing guidelines; and talking about his family life.

This oral history interview with William L. Dickson was conducted by Jim Strassmaier at Dickson's apartment in San Diego, California, from September 25-26, 1991. In this interview, Dickson discusses his family background and early life in Portland, Oregon, including contracting polio while in high school and his early interest in politics, including his admiration of Franklin D. Roosevelt as a fellow polio survivor. He then discusses attending Northwestern Law School and many of his professors; clerking at the probate court in Portland; his family's religious faith; and getting started in a law practice in Portland. He talks about his experience as a debt collector during the Depression; his first run for the Oregon Legislature in 1930; and meeting his wife, Dorothy Adelaide Unk, in 1931.

Dickson goes on to discuss his time in the Oregon House of Representatives from 1933 to 1936, and in the Oregon Senate from 1937 to 1939, including his desire to help people burdened by debt; coordinating with his uncle, Ashby Dickson, to pass a constitutional amendment making judges nonpartisan positions; and legislation he worked on, particularly on the probate and guardianship code. He also talks about the role of lobbyists; the pay scale for legislators; and many of the legislators he served with, including Nan Wood Honeyman, Monroe Sweetland, and Frank Lonergan. He discusses his involvement with the Democratic Party; the impact of the Depression on his politics and career; and New Deal legislation.

Dickson then discusses his career after leaving the Legislature. He talks about working for the federal Department of Justice during World War II, particularly his work on cases involving land condemnation for military use, and arguing before Judge James Alger Fee. He then talks about serving as a judge on the Circuit Court of Multnomah County from 1954 to 1973. He discusses cases involving mental health and guardianship. He then talks about the lives and careers of his children. Dickson closes the interview with a discussion of national politics in the 1990s.

This oral history interview with Windsor Calkins was conducted by Jim Strassmaier in Calkins' office in Eugene, Oregon, from July 7 to August 1, 1986. In the interview, Calkins discusses his family background and early life in Eugene, including a 1922 trip on foot from Newport to Florence, Oregon, with his father. He also discusses his father's career as a court reporter, as well as his own interest in the law. Calkins talks about studying law at the University of Oregon, including taking classes from Wayne Morse. Calkins talks about practicing law in Eugene and some of the cases he argued, including bootlegging and murder cases. He also discusses the effect the Depression had on his family. He then talks about his experiences in the U.S. Navy during World War II. Calkins also talks about notable people from Eugene, including William G. East and other judges. He then discusses his work as a lawyer for the Eugene Water and Electric Board and Sacred Heart Hospital, as well as his involvement with the Lane County Bar Association, the Eugene City Health Board, and other civic organizations. He closes the interview with a description of malpractice lawsuits, as well as his family life.