The present high school was completed as part of the Public Works Projects started by President Franklin D. Roosevelt to provide jobs.

[3]: 160 City High School was built through the Public Works Projects, one of many other programs formed in Franklin D. Roosevelt's New Deal package.

The Morningside location was favored, and the school was built on top of a large hill outside of town.

Over time, the city's suburban expansion reached the school, enclosed it, and the expanded past it.

[4] City High ranks in the top ten schools for academic performance in Iowa.

[citation needed] Sports Illustrated named City High the top sports school in the state of Iowa, citing the school's dominant cross country, track, and football teams.

[17] In 2021, City High won best Drumline at the Muskie Marching Invitational, led by center snare Adam Bywater.

[18] In the spring of 2024, City High's most prestigious band led by Mike Kowbel, the City High Wind Ensemble, won a spot to the 97th annual Iowa Bandmasters Association Conference, and traveled to Des Moines, Iowa, to attend and perform.

Kennedy was named the Dow Jones Newspaper Fund Journalism Teacher of the Year in 1993 and inducted to the Iowa High School Press Association Hall of Fame in 1996.

In November 2012, it received 5th Place Best of Show at the JEA/NSPA San Antonio National Journalism Conference.