Life

My Father’s Obituary: Robert Wilson Winn Jr

Bob Winn went home.

It’s with a heavy heart that we announce the passing of Geauga County legend, Robert (Bob) Wilson Winn Jr.

Husband to Karen Winn and father to Keith (Debbie) and Tony (Amanda) Winn, “Blue Eyes” was born January 28, 1939, in Cleveland, Ohio, to Robert and Dolly Winn.

 He grew up with his sister Jewel in one of the only Black families in an Italian and Jewish neighborhood & it was here that Bob developed his love for life and grew his uncanny ability to see people beyond color and instead for who they truly are.

People.

After graduating from John Adams High School in 1958, Bob served in the U.S. Army as a tank commander in the General’s Company and welcomed his first son, Keith Winn.

 Following his service, Bob moved out to Geauga County with his sister, brother-in-law (Ted Paynther), nieces & nephews, and that’s where the legend was born.

Many of you knew him as a Deputy Sheriff in Geauga County. He is perhaps one of the only law enforcement officials to ever throw someone in jail and have that same person later in life smile and buy him a beer time and time again.

 Because Bob loved serving the county and the people who lived in it, as anyone wearing a badge should.

 He believed in second chances, in not judging someone on their worst day, and in serving people with an infectious smile.

Bob was so beloved in the county that people would often leave fully cooked meals inside their mailbox because they wanted to make him happy. And nothing made Bob happier than a hot meal.

 What a life he lived.

 After his time as a Deputy Sheriff, Bob worked as a security guard for the Cleveland Public School System. It was there his infectious energy went on to change the lives of many young men and women in Northeast Ohio.

He was respected not because of what he could physically accomplish, but because he was often one of the only people who gave the kids a chance and saw them as people.

 He would often buy them McDonald’s, give them rides home from school, and be a strong father figure in a world that needed one.

 Later in life, Bob had the joy of being a grandfather to Josh (Stephanie), Jarrod, and Kayla Winn, and a great-grandfather to Presley, Weston, and Rylie Winn, whom he loved fiercely.  He leaves behind his wife, sons, daughters-in-law, nieces, nephews, cousins, family, and friends, who all had the pleasure of knowing him.

And through it all, you should know Bob loved life and the people and animals who made it meaningful. He believed in treating people with respect, knew the value of a well-timed joke, and always offered a helping hand when at times it would have been easier to offer a fist.

He was fiercely loved by his family and his community, which made going shopping with him an absolute nightmare… err—joy.

Bob wanted you to know: if you’re reading this, he loved you and he wants you to be happy.

He would remind you to never confuse kindness for weakness, that it’s OK to (excessively) feed the dog, and to always see the best in people, because it’s the only medicine that grows hope.

 His life taught us that respect is on the other side of being your authentic self, and what a gift that is.

May we all follow his example.

The family invites you to join us in a celebration of life on Thursday, December 4th, 3–7 PM, at St. John Funeral Home, 16381 Chillicothe Road, Chagrin Falls, Ohio 44023 followed by his funeral service on Friday, December 5th, 2025, at 11 AM, at Valley Presbyterian Church, 17560 Chillicothe Road, Chagrin Falls, Ohio 44023.

 It was great loving you, Bob, and his memory will live on in the stories you share.

And for what it’s worth, if you mention his name when you go to the bathroom, you just might get a good seat.

We love you Bob!

Please like, comment, share, and tell me what you think. I apologize for being out of pocket. It’s been one hell of a week!

72 thoughts on “My Father’s Obituary: Robert Wilson Winn Jr”

  11. What a marvelous obit and the triumphal counterpoint to Thugs with masked mugs AKA ICE. Wish we had more like him nowadays. Heck of a great guy. Sorry for you loss. My Dad would have been 100 on Tuesday, but he died about 10 years ago. Still missed.

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  16. Oh, Tony… I never had the honour of knowing Bob, but reading this made me feel the warmth he carried into every life he touched. His kindness, his humour, and his ability to truly see people shine through these memories. I am so sorry for your loss, and grateful you shared a little of him with us. May his spirit of generosity and gentleness stay with everyone who loved him.

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  21. Beautiful commemoration. Clear and heartfelt, and I felt like I was right there with you as I read. Others will appreciate your words immensely during this time. My prayers and love to you and yours. What a beautiful time of year for him to take his leave.

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  25. Peace and blessings, Tony. My sincerest condolences to you and your family. Your father was an incredibly handsome man. You look a lot like him.

    The obituary isn’t drab and tortuously sad, and I truly appreciate that as a reader of it. Having a little bit of humor added to it as well is a smart move. 🙏🏾🩵

    I hope both services will be joyful, peaceful, inviting, and memorable.

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  29. “My heartfelt condolences to you and your family as you honor a life truly well-lived. Bob’s impact continues to resonate, and his legacy remains a lasting testament to the remarkable person he is.”

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  30. What a remarkable tribute to Bob Winn! His life was a testament to the power of kindness, compassion, and authenticity. Here are some thoughts that come to mind:A life well-lived: Bob’s story is a reminder that our lives are made up of moments, interactions, and relationships. He left an indelible mark on the lives of those who knew him, and his legacy will continue to inspire others.Breaking down barriers: Bob’s ability to see beyond people’s surface-level characteristics and connect with them on a deeper level is a valuable lesson for us all. He showed that everyone deserves respect, kindness, and understanding.Service and community: Bob’s dedication to serving others, whether as a Deputy Sheriff, security guard, or simply as a friend and family member, is a shining example of what it means to live a life of purpose.The power of kindness: Bob’s infectious smile, generosity, and kindness inspired others to do the same. His story reminds us that even small acts of kindness can have a profound impact on someone’s life.Authenticity and vulnerability: Bob’s authenticity and willingness to be himself, without apology, is a valuable lesson for us all. He showed that it’s okay to be vulnerable, to make mistakes, and to learn from them.As you mentioned, Bob’s story will live on through the countless lives he touched. His family, friends, and community will continue to share stories, laugh, and cry together, celebrating his life and legacy.In the words of Bob Winn: “Never confuse kindness for weakness… It’s okay to be yourself… Always see the best in people.” What a wonderful way to live, and what a wonderful way to be remembered.

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  35. So sorry to hear about your loss, Anthony. Keeping you and your family in my thoughts and prayers. From reading Bob’s obituary, I can see a lot of him in you.😊

    Thank you for sharing his words of wisdom—

    “…respect is on the other side of being your authentic self….” It’s true.

    Always be you!🙏🏽💕

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  37. Sorry to read this, Tony… I will take “never confuse kindness for weakness” as his gift to someone whom he never knew but can still benefit from his lifetime wisdom…

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  40. Oh I’m so sorry for your loss. He sounded like an amazing man – so much to like. “He believed in second chances, in not judging someone on their worst day, and in serving people with an infectious smile.” What an amazing tribute. Thinking of you.

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  41. Shew, Tony. I’m so sorry to hear about your dad. There we were having a meeting last week and talking about Thanksgiving and it must have been such a tough time for you. Which makes me extra thankful and appreciative for the time you spent with me. Kind regards from Renee Bonorchis

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  43. I’m so sorry you have lost your father, Tony. What a beautiful face and smile he had! He must have been such a joy to be around and then to have him as a father—what a great gift! I hope your family is comforting you today and throughout the days ahead.

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  44. Really sorry to hear about your Dad, Tony. It really sounds like he lived his best life as an inspiring man! This is a beautiful tribute that’d make any father proud.

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