He continued there until he entered the United States Navy as a Lieutenant, junior grade at the outbreak of World War II.

[3][4] In 1948, after encouragement from Paul Douglas and Adlai Stevenson he ran for DuPage County State's Attorney and received the highest vote total of anyone up to that time, but lost.

[2] In his third run for office, Redmond won a seat in the Illinois House's 36th district, which included all of DuPage County.

[10] He sponsored many pieces of legislation during his tenure including the creation of an Equality of Economic Opportunity Commission, created the Illinois State Board of Education,[2] and advocated for increased mass transportation for his suburban district.

Governor Dan Walker objected to Choate for personal reasons and supported Gerald A. Bradley of Bloomington.

J. Glenn Schneider of Naperville, a legislator from Redmond's DuPage County, had reservations about a Choate speakership.

No candidate, which at various points in time included up to eleven Democrats and the Republican leader James R. Washburn could get the 89 votes required to be elected Speaker.

[12][13] Redmond became a respected legislator on both sides of the aisle and during the 79th General Assembly; he was elected Speaker of the House as a compromise candidate.

[5] As Speaker, he took a hands off approach with legislation and toured areas of downstate Illinois that may have otherwise not met anyone from the Democratic leadership.