[1] Tutored by James Lane Allen as a young man, Breckinridge attended State College (now University of Kentucky) in 1880–81, before he graduated from Lawrenceville School in New Jersey.

He served as an aide-de-camp to his uncle, Major General Joseph Cabell Breckinridge Sr., during the Spanish–American War.

Editorials and articles covered juvenile justice, education, tuberculosis commissions, crime and the penal system, environmental issues, gun control, and anti-lynching laws.

Breckinridge co-founded the Fayette Home Telephone Company in 1899,[4] and he invested in land deals both in the Bluegrass and eastern Kentucky.

[3] Nearly a decade after Madeline's death, Desha married the widow Mary Frazer LeBus.