Robert W. 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.

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!