Dennis Ray Winfrey, 83, passed away of natural causes at his home in Springfield Missouri on Jan 19th 2025. Dennis was born in Joplin, MO on March 21, 1941, to Charles Winfrey, Jr. and Millie Winfrey. After his father ended his service in WWII, the family moved to Neodesha, KS, where he graduated from Neodesha HS in 1959. It was there that he met the love of his life, Peggy Sue Talley. He accepted a football scholarship to Kansas State University. Dennis was a co-captain during his senior year and a multiple year letterman. He graduated with a Bachelors degree in 1963 and went on to pursue graduate classes in Education until the completion of his scholarship in 1964.
Dennis was devoted to Peggy, and she to him. They were “the image” of high school sweethearts – the jock (Dennis the Menace) and the cheerleader (sweet Peggy Sue). They enjoyed many school dances and “picture shows by the hour”. Dennis and Peggy married on July 1, 1962, while he was still at Kansas State. They lived in a small apartment “under the arena” then moved to married student housing. They bought a boat and spent summers waterskiing on Tuttle Creek Lake.
Dennis & Peggy moved from Manhattan KS to Oklahoma City, where Dennis excelled at a career in insurance, winning a sales trip to the Bahamas. It was in Oklahoma that they grew their family adding daughter Denise Rene’ in 1967 and son Derron Ray in 1970. Shortly after Derron was born, they moved back to Neodesha KS. They opened the Old Homestead restaurant and private club with Richard and Joyce Talley. Later adding a Bunkhouse Hotel and Banquet Hall. Dennis could be found working the restaurant super club in the evenings. As a man of many talents, he could be tending the Bar, Chef, Bouncer or going table to table with his guitar singing requested songs to patrons. After selling the establishment in 1981, Dennis pursued a career in the oil & gas industry of the Southeast Kansas region for several years. In 1994 Dennis & Peggy moved to Springfield MO to pursue new business opportunities. He was joined by his son and his family in 1999. Together they built multiple businesses and grew those companies, enjoying success of being recognized for several local and national business awards. Dennis and Derron sold their software processing company (Softgate Systems) in 2011 to a business who was later acquired by PayPal, in 2018 they sold Electronic Check Services and ECS Prepaid giving room for Dennis’s retirement.
He was a devoted Kansas State Wildcat fan and season ticket holder. He very much enjoyed seeing the Wildcats rise under Coach Bill Snyder. Dennis and son Derron attended many games and traveled to Bowl Games together over the years. As a Golden Cat (former player), he was able to experience the excitement close-up with annual sideline visits and facility tours, with the highlight of being able to see his name plaque in the current K-State Football locker room as a noted former player. On his name plate is the slogan “Don’t Accept Losing”. When he was unable to attend in person, he was watching games intently at home and reviewing old games on recordings.
He is survived by his adoring wife Peggy and two children – Denise (George) Sabol of Liberty, MO, and Derron (Paula) Winfrey of Springfield, MO. They have 4 grandchildren – Katrina, Chelsie, Paul, and Brendan – and 6 great-grandchildren.
He was preceded in death by his parents Charles Jr. and Millie Winfrey, brothers Charles Winfrey III, Wayne Winfrey, and sister Phyllis Wendling.
Funeral Service will be held Friday January 24th at 10am at Greenlawn Funeral Home (North) 3506 N National Ave, Springfield MO 65803 in the main Chapel. Burial will follow the service at Greenlawn’s Memorial Gardens North of Springfield. The family will be receiving friends on Thursday January 23rd from 4pm to 6pm at the North Greenlawn Funeral Home.