In Loving Memory of Richard C. Milkie
April 15, 2026
Founder of Dick’s Roof Repair Service
Richard “Dick” C. Milkie passed away on March 13, 2026, leaving behind a remarkable legacy rooted in family, craftsmanship, and community.
Born on April 16, 1935, in Racine, Wisconsin, to Jerome and Alice (Riekkoff) Milkie, Dick grew up with a strong sense of discipline and determination. He attended St. John’s Sacred Heart and St. Edward’s Grade Schools and graduated from St. Catherine’s High School in 1953. A standout three-sport varsity athlete and senior Prom King, Dick’s accomplishments later earned him induction into both the St. Catherine’s and St. Joseph Hall of Fames.
In 1954, Dick met Marion Gordon, the woman who would become his lifelong partner. They married on April 28, 1956, beginning nearly 70 years of marriage filled with love, resilience, and shared purpose. Together, they raised five children and built a family that remains at the heart of Dick’s legacy.
Dick’s professional journey began humbly, working part-time as a roofer alongside his father while holding a full-time position at Western Publishing. In 1957, he founded Dick’s Roof Repair Service. What began as a side endeavor grew steadily through grit and reputation until 1975, when Dick committed to the business full-time. Today, the company remains proudly family-owned, led by his son Jeff and supported by the third generation, a living testament to Dick’s work ethic and vision.
After settling in Kenosha in 1962, Dick became deeply involved in the community. He dedicated more than 25 years to coaching football and basketball through the CYC and founded the Small Fry Basketball program in 1972. Over the decades, he mentored countless young people, leaving a lasting impression through encouragement, leadership, and kindness.
Dick’s life extended well beyond work. He had a deep love for fishing, with cherished trips to northern Wisconsin, Minnesota, and Canada. Whether reeling in walleye with friends or enjoying quiet mornings at the family cabin on Lake Buckatabon, those moments were among his most treasured. In later years, he spent winters in Naples, Florida, enjoying golf and warm weather. At Big Oaks Golf Course, he became something of a legend for his hobby of collecting lost golf balls, proudly tallying more than 300,000 over the years.
Known for his easygoing personality and gift for storytelling, Dick brought warmth and humor wherever he went. He took immense pride in his children and grandchildren, supporting them through years of coaching, spectating, and encouragement. A devoted Catholic and longtime member of St. Mary’s Catholic Church in Kenosha, he quietly gave back, especially during the Christmas season through charitable outreach.
Dick approached life with gratitude and perspective, often reminding those around him, “Life is just a short vacation.” It was a philosophy he truly lived.
His legacy endures in the family he loved, the business he built, and the countless lives he touched along the way.
