[2] Redmond served as a cadet colonel in the Citizens' Military Training Camp program at Fort Leavenworth, where he also won awards, including the 1937 Pershing medal, naming him the outstanding CMTC trainee in the Seventh corps area.
[2] He wanted to become a lawyer, however he abandoned these ambitions due to the financial struggles his family was enduring amid the Great Depression making him unable to attend law school.
[5] From 1942 through 1945, amid World War II, Redmond took a three-and-one-half year military leave to serve in the United States Army, in which he advanced in classification from second lieutenant to lieutenant colonel, serving as an assignment officer in the Adjunct General's Department at the Camp Wolters infantry center.
[7] At Northwestern he met competent individuals who he hired as assistants to help reorganize the school district's purchasing department.
[6] Redmond would serve four years as the head of the purchasing department, before taking the job of superintendent in New Orleans.
[7] Redmond received national recognition in the educating community for his work in enhancing school administration in Chicago.
[10] There was even consideration of appointing Redmond as Hunt's successor in the role of superintendent of Chicago Public Schools.
[9] During his tenure, in November 1958, a powerful homemade bomb was exploded in front of his private parking spot at the central administrative offices of the school board.
[14] In February 1959, an article in The New Republic brought to many people's attention that no organized effort had arisen to integrate the schools in New Orleans.
On August 31, 1960, members of the school board requested a delay in integration to allow more time to prepare a plan, which was granted, moving the slated date of the start of desegregation to November 14, 1960.
They rejected this suggestion, arguing that it would be too subjective a criteria, and opting instead to use a "scientific" method which instead wound up choosing the schools which appeared most ill-welcoming of integration.
[23] In February 1961, Redmond announced he did not plan to renew his contract with the school district in New Orleans, which was to expire on July 1, 1961, at which point he intended to leave.
[23] He moved to New York, where he was hired as a director of school administration services by Booz Allen Hamilton Management.
[28] Since Benjamin Willis had resigned effective August 31, but Redmond could not leave his post in Syosset before October 3, the Chicago Board of Education appointed an interim superintendent, Thaddeus Lubera, for the intervening days between their tenures.
[29] Upon taking the job, Redmond declared that he was setting out to prove that Chicago's, "big-city school system is not doomed to failure.
A recurrent issue was the school district lacking sufficient funds to meet the demands of the union.
Daley would give the Union what they wanted, and promise he would help the Chicago Board of Education receive additional funding.
[40] The strike ended May 26, 1969, after intervention by Mayor Daley and Governor of Illinois Richard B. Ogilvie succeeded in reaching an agreement.
[41] However, by the middle of the summer of 1969, it became evident that the Chicago Board of Education would struggle to financially hold its contractual obligations.
[43] On August 28, 1969, due to new money being made available, the Chicago Board of Education agreed that it would implement it 1969 contract to a degree that satisfied the union, averting a second strike.
This document, most commonly referred to as "The Redmond Plan", was accepted "in principle" by the Chicago Board of Education on August 23, 1967, by a 10–0 vote (with one abstention).
[50] In August 1968, Redmond testified before the Illinois Senate that he believed desegregation busing to be vital to increase integration in the city's schools.
"[16] Redmond moved to Benton Harbor, Michigan, working as a management consultant for the international accounting firm Coopers & Lybrand.