Middletown mourns death of beloved former football coach Dick Wolslayer

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Coach Dick Wolslayer with his daughter, Kelly, at a recent football game against rival Port Jervis. (Photo Credit: Enlarged City School District of Middletown.)

MIDDLETOWN – Legendary former Middletown football coach Richard “Dick” Wolslayer has died at the age of 84.

Wolslayer was the winningest football coach in school history. He was part of the inaugural 2023 Middletown Wall of Fame class, as one of just seven members, and was the first coach enshrined. A multi-sport field on Monhagen Avenue in the City of Middletown is named after Wolslayer, who was beloved in the community.

“Coach Wolslayer loved Middletown High School and was a positive influence on so many,” City of Middletown Mayor Joe DeStefano said. “He was well respected and was honored that we built a youth stadium and named it after him to honor him. I am so happy we were able to complete the project so he could soak up that moment.”

Wolslayer took over as Middletown’s head coach in 1967. He held the position until 1978, then again from 1983-95. His 142 victories are a school record. Wolslayer also taught in the district for 33 years.

“Coach Wolslayer was the best coach Middletown ever had,” said J. Miguel Rodrigues, the City of Middletown’s Common Council president. “He was a true gentleman all around and I am glad to name Wolslayer Field after him. It is nice to see young kids and families call it Wolslayer Field.”




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