Bailey Family Collection

Jesse W. Bailey (1833-1885) was born to Jesse Bailey and Elizabeth Woodson Bailey. In 1874 he married Bettie Franklin Looney (1850-1900) in Henry County, Tennessee. The couple had two daughters, Looney Franklin Bailey and Jesse William Bailey. The bulk of the collection consists of documents and photographs pertaining to these two women and their immediate family members.

Looney Franklin Bailey (1875-1952) attended the Clarksville Female Academy, graduating in 1893. The collection includes several of her monthly grade reports from the school dating 1886-1888, along with her commencement materials. She married William Walter MacLaughlin (1869-1947) in 1898, and the couple moved into the Bailey family home at 1033 Madison Street. Following the death of Looney’s mother in 1900 Looney and William inherited the Bailey family home and continued to live there for the remainder of their lives. The couple had three children, William Walter MacLaughlin, Jr. (1898-1967), Betty Looney MacLaughlin (1907-1908) and Jesse Bailey MacLaughlin (1911-1996). School records for both William and Jesse are included in the collection.

Looney Bailey’s sister, Jesse William Bailey (1884-1974) also attended the Clarksville Female academy, graduating in 1902. Jesse never married and spent many years working to help supplement the incomes of various family members, including her sister Looney MacLaughlin and her husband William. With the help of the Methodist Church, she moved to Philadelphia, Pennsylvania sometime in the early 1920s to work at a Y.W.C.A. branch. According to the 1930 census she was working as the director of the Harkness House Y.W.C.A. It is uncertain exactly when she returned to Clarksville from Philadelphia, but in the collection there are letters from her cousin Ellyn Dennes Danforth addressed to Jesse W. Bailey in Philadelphia as late as 1946. Eventually Bailey returned to Clarksville where she continued to live in the Bailey family home on Madison St. Her sister Looney MacLaughlin left the property to Jesse in her will. Jesse in turn sold the property to her niece, Jesse Bailey MacLaughlin Killebrew in 1953. Jesse W. Bailey remained in Clarksville until her death in 1974.

Jesse Bailey MacLaughlin married Jack Walker Killebrew, Sr. (1903-1971) on June 30, 1930 at the family home on 1033 Madison St. They had two sons, Jack “Jackie” Walker Killebrew, Jr. (1937-2000) and William Edwin Killebrew, Sr. (1945- ), both raised in the family home at 1033 Madison St. Photographs documenting Jesse Bailey’s life can be found in this collection, as well as childhood photographs of Jack and William.

Jack, Jr. attended Castle Heights Military Academy in Lebanon, TN., graduating in 1954. He served as a Private First Class in the Army and later became a partner at Killebrew & Company, a local hardware store. Jack never married and died in 2000 at the Veteran’s Hospital in Nashville, TN. William graduated from Clarksville High School in 1964 where he was an avid bowler and member of the golf team. He became the writer of “The Strike Zone,” a bowling report for the Leaf-Chronicle. In 1969 William married Roxanne Martha Downs (1945-1985), and the couple relocated to her hometown of Cincinnatus, NY, where they raised three children.