Now, the future the historic high school remains unclear as the more than 500 students continue sharing space in another building.
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The reminiscence of the school is a stately and impressive building, but a closer look shows wear and tear from years of neglect.
Ongoing problems with heating the school reached the breaking point last February when the pipes burst during the polar vortex, leaving it vacant ever since.
"I've been watching the demise of this much loved high school," said Chuck Hughes, president and CEO of Gary's Chamber of Commerce. Hughes is also a proud alumni of Roosevelt.
The school was built in the 1920's just for African American students during the era of segregation.
Hughes said he and his classmates were proud to represent their school, which was once a vibrant part of the community. The building is even listed on the National Register of Historic Places.
But with nearly $15-million worth of repairs needed, Hughes isn't sure the building can be saved.
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"It kind of breaks your heart when you go to these sprawling suburban schools and see the conditions our kids have to learn in and wonder why they can't learn," Hughes said.
Roosevelt students have been temporarily placed at the Gary Area Career Center.
Alumni, like Lovetta Tindal, are now hoping grants and donations can fund plans to repurpose the building to a multi-use community center.
"Some people may think we're focusing too much on the building, but this is a structure that represents quality and excellence," she said.
The fate of this building is in the hands of the DUAB.