Cover for Carroll Bob Winn's Obituary

Carroll Bob Winn

June 24, 1944 — February 7, 2026

Carroll Winn was born on June 24, 1944, in Tyler, Texas. He lived a full, creative, joy-filled life defined by family, artistry, laughter, and an unwavering willingness to show up for the people he loved.

He was preceded in death by his parents, Bobbie and Howard Winn; his brother, Jerry Winn; his cousin, Ken Lillard; his son, Kelly Winn; and his beloved wife, Kay Winn.

Carroll attended Robert E. Lee High School before going on to the University of Texas at Austin, where he majored in business. During his time there, he witnessed one of the university's most infamous moments, the 1966 UT Tower shooting.

After college, he began his career in the restaurant business before transitioning into real estate, where he built a respected and successful career. He approached both business and life with creativity, intuition, and determination.

Carroll was an extraordinarily gifted artist. He drew and painted with remarkable talent, created intricate stained glass, and used his artistic eye to design and build several unique homes during his career. Forty years after graduation, his high school art teacher reached out to ask whether he had pursued art professionally, saying he had never taught a more talented student.

Above all else, he was a devoted father to Courtney and Kelly and a proud grandfather to Ella, Claire, Lennon, and Mike. Because of his ornery nature, his grandchildren affectionately called him "Boom Boom," a role he cherished. He was present, supportive, and always ready with advice or a helping hand. You could often find him doing arts and crafts, getting his fingernails painted by his granddaughters, or beaming with pride at a soccer game.

Carroll had a mischievous streak and a wry sense of humor that kept everyone on their toes. He had a talent for stirring up just enough "good trouble" to make life interesting. In his twenties, while living with roommates, he carefully orchestrated a prank that he knew would send one roommate into a rage. Anticipating the chase, he cleared a perfect path through the house for his escape. The plan worked. His roommate bolted after him exactly as expected. Everything was perfectly arranged... except someone had closed the sliding glass door.

He ran full speed straight into it.

He later said that in that split second, he knew if he stopped, he would be cut to pieces so he kept running. He went straight through the door without a single scratch. That story became more than one of his classic tales; it was a metaphor for how he lived. Obstacles might hinder or hurt some, but not him. Life's trials never sliced him up. He moved through them, laughed at himself, learned from them, and kept going.

This is what I admired most about my dad, his ability to look in the mirror, take responsibility for what he did not like, and take action to become the best version of himself. He did this without shame or pride, inviting those he loved to help keep him accountable.

Carroll Winn was truly one of a kind. He met life's challenges the same way he met that glass door...full speed, with courage, humor, and heart.

He will be deeply missed and forever remembered.

To order memorial trees or send flowers to the family in memory of Carroll Bob Winn, please visit our flower store.

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Graveside Service

Friday, February 27, 2026

12:00 - 1:00 pm (Central time)

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