Leonard was raised in Renville County, Minn., and moved to Birch Coulee Township. His 1918 draft registration card indicates he was a self-employed farmer at RFD 1, Olivia, Minn. He was also a farmer in Norfolk Township, Renville County, Minn. He bought his first car in 1915. Leonard and his son Thomas went to Flint, Mich., to work in a car factory, then a dairy. In the 1930's he worked for the Works Progess Administration in Minneapolis. When his second wife Emma inherited $1000 in about 1935, they bought another farm north of Bird Island. In the same decade, Leonard had a stroke that resulted in a stuttering speech impediment. In 1952, Leonard had a second stroke that rendered him speechless, although he continued to work. He died in Olivia, Minn., in 1956.