[12] During the late 1940s, a wave of new students began to enter the Portland school system as a result of the post-war baby boom.

In response, voters approved a $25 million building levy in 1947 with the goal of constructing, renovating, and expanding schools across Portland.

[13] Roosevelt, in particular, was described as Portland's "worst crowded high school" in 1950, with needs including the completion of a wing already under construction and the addition of a new gymnasium.

Roosevelt began a modernization process in 2015 as part of a $482 million bond measure aimed at improving schools across Portland.

[22] The project included a new wing for the school – with a community center, gymnasium, and commons area, among other additions – and renovations to the original 1921 structure.

The modernization project was praised by the Business Tribune, which cited its "intertwining benefits of seismic stabilization, historic preservation and improved learning environments".