Raymond Joseph Winkelman, 73, of Ashland, died Thursday, April 3, 2014, at Boone Hospital Center in Columbia, Missouri. He was born July 15, 1940, in Brinktown, Missouri, the son of the late Adolph Stephen and Hilda Anna Marie (Brune) Winkelman. He was united in marriage on August 4, 1962, in Brinktown, to Betty Ann Kleffner who survives at the home. Ray attended airline school in Oklahoma after graduating from Helias High School and was hired by Ozark Airlines in 1959. He continued working with Ozark in Champagne, Illinois and Columbia, Missouri. In 1986, he was transferred to St. Louis with TWA. He retired after 33 years in the airline industry. He then drove a mail truck for a private contractor until two years ago when he retired. Ray also held a private pilot license in his earlier years. Ray was a member of Sacred Heart Catholic Church in Columbia where he served on the Parish Council, was a Lector and was a Eucharistic Minister for Nursing Homes. He also was a member of the Knights of Columbus. Ray always put others' needs before his own. He was a gentle and caring man who enjoyed his family, grandchildren, farming, and playing cards. He also enjoyed hunting and fishing. In addition to his wife, Betty, he is survived by four children, Cindy (Rick) Harmon, Ashland; Shelly (Buck) Garrett, Ashland; Brenda (Scott) Duncan, Holts Summit; Tina (Michael) Krumpelman, Marceline; eleven grandchildren, Lindell and Derek Harmon; Elizabeth Garrett; Christopher, Joseph, and Michael Duncan; Hayden, Rha, William, Kylee, and Lexie Krumpelman; and five siblings, Edmund (Anna Marie) Winkelman, New Bloomfield; James (JoAnn) Winkelman, Jefferson City; Gerald (Patrice) Winkelman, Denver, Co; Anna Mae (Lawrence) Redel, Jefferson City; and Carolyn (Louis) Freidinger, Jefferson City. Mass of Christian Burial will be 11 a.m. Monday, April 7, 2014, at Holy Guardian Angels Catholic Church in Brinktown, Missouri with the Rev. Msgr. Marion J. Makarewicz officiating. Burial will be in Holy Guardian Angels Cemetery. Visitation will be 2-5 p.m. Sunday at Dulle-Trimble Funeral Home in Jefferson City with a prayer service at 5 p.m. Additional Visitation will be 10-11 a.m. Monday at the church. Memorials are suggested to Mass Intentions or to the wishes of the family. Those wishing to email tributes or condolences to the family may do so at the www.dulletrimble.com website.