Of all the photos Sarah has shared with us, this is one of my favorites. It's your great grandfather, Charles Bennett Ware (Kathleen Ware's father), in full uniform. I asked Sarah about the uniform, but she didn't have any info on his military service.
I once did a drawing of Teddy Roosevelt which featured a pin identical to the one on Ware's hat, and because it seemed he would have been of age to fight in the Spanish American War, I started by researching uniforms from that war. I got a match. Next, I looked up Spanish American War service records and got a hit on Charles Ware. Turns out, he served as a corporal in the Spanish American War, in Company E of the Illinois Infantry.