Robert Woolwine, Jr.

Robert Woolwine, Jr., a beloved father, grandfather, brother, and friend, passed away peacefully on March 10, 2025, in Madeira, Ohio, surrounded by his loving family. Born on October 27, 1948, in Winchester, Kentucky, Robert lived a life marked by warmth, laughter, and an unwavering dedication to those he loved.

Robert was a successful salesman in the TeleCommunication industry, a career that showcased his exceptional ability to connect with others. Even after retirement, he remained industrious, delivering auto parts several days a week, a testament to his tireless spirit and desire to stay active. Family and friends knew him affectionately as both Robert and Bob, depending on the setting, but regardless of the name used, he was universally recognized for his kind heart and engaging personality.

One of the many charms of Robert was his great sense of humor. He had a silly rhyme for just about everything, and it would invariably make you laugh, no matter how many times you heard it. During the challenging times of the pandemic in 2020, he took it upon himself to ensure that his family could still vacation together, creating precious memories that will surely be cherished for generations to come. Robert had a deep love for the water, enjoying life on his boat in Charleston, SC, and spending countless joyful moments on his houseboat at Lake Cumberland.

His passions extended beyond the water; he was an avid traveler, particularly drawn to the South, and enjoyed fishing in every lake across Kentucky—legend has it he even caught a magnificent 4-foot Muskie at Dale Hollow. Additionally, Robert found immense joy in being a pitching coach for both of his sons in baseball and golfing and proudly celebrated two remarkable hole-in-ones throughout his adventures on the greens.

Family was at the heart of Robert's existence. He loved fiercely and prioritized their happiness above his own. He was a loyal family member and remarkably caring friend, always willing to listen and engage with anyone, making new friends wherever he went. His pride in his family was evident; he cherished the opportunity to share new and varied experiences with his children.

He leaves behind a loving family that includes his daughter, Christy (Billy) Woolwine-Lykins; sons, Jason (Erin) Woolwine and Harrison Woolwine; grandson, Jackson Woolwine; sister, Pam (David) Spears; and sister-in-law, Deborah Woolwine. He also held dear; his aunt Delores; nieces and nephews, Joy Walstrum, Sarah (Jay) Stewart, and Morgan Spear II as well as his niece, Heather Woolwine and nephew, Matthew (Jill) Woolwine, whom he loved as if they were his own children. Robert also cherished his many great-nieces and great-nephews.

Robert is preceded in death by his father, Robert Woolwine, Sr.; mother, Iva (nee Blanton) Gardner Sharp; and brother, Tommy Woolwine.

In this bittersweet moment of remembrance, we celebrate the incredible life of Robert Woolwine, Jr., who filled our hearts with love, laughter, and lasting memories. He will be deeply missed but forever cherished by all who had the honor of knowing him. As we reflect on his life, let us carry forward his legacy of kindness, humor, and unwavering love for family.

If desired, memorial donations may be directed to VITAS Hospice.