A St. Louis native, he married Patricia Fawcett in 1956. He attended Saint Louis University and received a degree in pharmacy from the College of Pharmacy in 1957. Deacon Winkelmann owned his own pharmacy, then later retired from National Supermarkets.

Deacon Winkelmann was ordained to the diaconate in 1995 by then-Archbishop Justin Rigali. He was assigned to Our Lady of Providence Parish in Crestwood from 1995 until 1998, when he was assigned to Epiphany Parish in south St. Louis. While at Epiphany, he also served as a campus minister at St. Louis Community College at Meramec and at the Washington University Newman Center. In 2006 he was then assigned to St. Justin Martyr where he served until his retirement in 2015.

As an active deacon, he performed the sacramental functions of a deacon, specifically assisting at Mass, conducting wake services and attending funerals, leading Liturgy of the Word and Communion Services when needed, performing baptisms, conducting benedictions and leading Stations of the Cross. Deacon Winkelman also worked in various sacramental preparation programs, young adult formation, adult education, outreach to the poor and the homebound. He managed the Gene Barron Educational Fund, served for many years as the spiritual director of the local St. Vincent DePaul conference and participated in many ecumenical affairs programs.

Survivors include his wife, Patricia Winkelmann; five children, Mary Tinsley and Christian Jr., William, Tim and Paul Winkelmann; 18 grandchildren; and eight great grandchildren. Deacon Winkelmann donated his body donated to science.