Leslie Gilmore was the youngest of the Kirkmans' children. Gilmore as a middle name comes from Isabella's brother-in-law, David Gilmore, a sea captain who married her sister Agnes. Growing up, Leslie attended Baker School in his neighborhood, Whitman Academy, and Whitman College. After college he went into partnership with Frank Clark to form the Clark-Kirkman Co. that operated The Togs, a clothing and shoe store. Later he joined his brother William Henry in managing the agricultural property left to them by their father.
Leslie married Mabelle Hawman and together they welcomed his mother Isabella, brother William Henry and his son, and sister Myrtle Belle into their home on Pearson Street after the “Red Brick House” was donated to Whitman College. Leslie and Mabelle had three children--a son Leslie and a set of twins Robert and Betty. Betty describes her father as a fun loving man and related a story of driving the children to a nearby frozen lake to do donuts in the car. Leslie was a member of both the Elks and the Masons. He died in 1944 and is buried at Mountain View Cemetery in the Kirkman Family Plot.