[7] After graduating from Trinidad High School, Woolf enrolled in Texas A&M College in 1941, but in 1943 left A&M to enter active duty in the US Army.

He was commissioned an officer in the United States Army Air Corps and served for three and one-half years.

[10] During Woolf's tenure as president, Arlington State College was elevated to a four-year institution effective September 1, 1959.

The college was authorized to offer seventeen bachelor's degree programs in business administration, engineering, liberal arts, and the sciences.

[14] Under Woolf's leadership, ASC was the first Texas A&M System school to integrate (1962) and the first to accept black athletes (1963).

[15] ASC, under Woolf's leadership, maintained the system of segregation despite the Supreme Court decisions of Sweatt v. Painter and Brown v. Board of Education.

Ernest Hooper, Leaston Chase, and Jerry Hanes approached the Dallas chapter of the National Association for the Advancement of Colored Peoples for assistance.

However, Woolf would not desegregate the faculty and staff, being quoted in Fort Worth Star-Telegram, on July 11, 1962, as saying "ASC has no plans now or in the future to hire (Black) teachers".

In this same letter he notified Harrington that the Athletic Council of the college was positive towards integration, likewise seeking the Board's guidance on the matter.

[24] Woolf was designated a "Distinguished Alumnus" of the College of Engineering of Purdue University in 1964, one of the first ten to be so honored.