His grandfather, Robert Boal, was also a state senator and was an associate of Abraham Lincoln.

Fort then returned to Illinois, assuming his father's farming and ranching interests.

[1] Fort was interested in politics at a young age, and was named to the Marshall County Republican Party Committee as soon as he turned eighteen.

In 1898, Fort visited Cuba, and convinced that war was imminent, raised a company of cavalry volunteers.

He was named captain of Troop L of the 1st Regiment Illinois Volunteer Cavalry when the Spanish–American War broke out.