Robert Middleton

Died: February 7, 2021
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Robert C. Middleton of Venice, Florida passed away unexpectedly on February 7, 2021. He was affectionately known by many as Bob and also known by the nickname “Smiley” because of his cheery disposition on life.

Born on February 27, 1959 to Kenneth and Virginia Middleton in Danville, Virginia. Bob was one of five children. After graduating from school, Bob’s love of food culture led him to work as a chef at many restaurants in Richmond, Virginia eventually opening several of his own throughout the years. He independently published River City Restaurant Review, a food review magazine in Richmond, VA. His culinary and people skills left behind a wonderful reputation that has him known up and down the East Coast.  Later in 2015, Bob relocated to Florida. He shared time with his father, Kenneth, during his final days. Briefly Bob cherished sharing a home with his loving big brother Edward “Les” Middleton. Les showed unconditional love and support to Bob in his final years as his friend, confident, and big brother. Once in Florida Bob took joy in working a food truck at Florida Southern collage. Finally, he went on to work for Bob’s Carpet in Venice.

On family vacation as a boy Bob fell in love with the ocean. His entire life he knew he wanted to live near the sea. In Venice, you could always find him by the water. One of Bob’s favorite things to do each year was to go to the different local beaches during hatching season and watch the baby turtles return to the ocean. Bob had a direct relationship with God, finding the sublime in natural beauty. He found peace in watching the sunset each night over the ocean.

Bob is survived by his loving daughter Aaron Middleton Webb of Henrico, Virginia. He also leaves behind his four siblings: Douglas (Brenda) Middleton of Glen Allen, Virginia, Edward (Loredana) Middleton of The Villages, Florida, Lisa Middleton of Barton, Florida, and Kenneth P. Middleton of Fredericksburg, Virginia.  He is preceded in death by his parents Kenneth R. and Virginia C. Middleton.

A Celebration of Life at Sea will be held in Bob’s honor later in June of 2021. For more information, please contact Edward Middleton by email at

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Timeline for Robert Middleton

December 26, 2016
Bob & one of his ladies :)
Bob & one of his ladies :)
January 21, 2017
Bob selling cars at Venice Nissan :)
Bob selling cars at Venice Nissan :)
September 16, 2016
Bob & his brother who was getting married :)
Bob & his brother who was getting married :)
Died: February 7, 2021

Condolences for Robert Middleton

Farley Funeral Homes and Crematory

Our sincere condolences.

The staff of Farley Funeral Homes and Crematory.


Loredana posted on 2/27/21

Happy Birthday in Heaven Bobby! Love you 😘😘😘🎈🎉🍷


Loredana posted on 2/19/21

Our family lost a sweet and kind man! Bobby, my brother in law, you will be missed by all of us ❤️ Say hi to Ken and Virginia for us! You are now part of the lights of the sunset that you loved so much! You are now part of another life...until we’ll see you again, xoxoxo Loredana


Steve Rock posted on 2/15/21

I met Bob in 1976 in Richmond when we were co-workers at O’Brienstein’s Restaurant in Regency Square Mall. We became fast friends from day one. Over the decades since then we were simpatico in everything. His family and mine were were one. We shared everything. Road trips to Myrtle Beach. Nashville. Atlanta. Savannah. DC. We saw concerts. The Dead. Little Feat. Too many more to mention. Bob was my brother from another mother. I will always cherish the memories. I am always going to miss him. I will always love him. Rest In Peace my friend. Why did you leave us so soon? Only God has an answer for that question. Peace


Valerie D. Bryant posted on 2/13/21

Bobby Shaftoe's gone to sea Silver buckles at his knee. I remember finding a vintage Bobby Shaftoe print and giving it to my brother in-law Bob for Christmas one year. I remember his grin when he unwrapped it, happy that I knew his childhood nickname. Every single thing I remember about Bob is a good memory. I don't think I've met anyone else in my life who was equally good at cooking and drawing and joking around and caring for other people and being a family man. His legacy lives on in his daughter Aaron who is everything that he was. Love you, Smiley.


DAVID THOMPSON posted on 2/12/21

Bob and I first met when we worked together at Rudees on the James in Richmond. I was Exec Chef he ran our Raw Bar. We clicked instantly. We later worked together as Area Sales Associates for Doughtie's Foods which later became SYSCO. I cannot begin to recount all of the times we had together. Bob would start each workday at my house with a cup of coffee and we generally watched an episode or two of Andy Griffith. To him I was Otis and to me he was Floyd. I was lucky enough to win a trip to Las Vegas in 2003 in a sales contest and took Bob as my guest. To thank me Bob had a money clip made for me with a $1 token from the Bellagio. I still carry that money clip in my pocket to this day, and everyday, 18 years later. He was a funny, kind, fun-loving, optimistic individual who I am blessed to have been close to for several years before he moved south. I spoke to him just before the holidays and it was wonderful hearing his voice. His passing has saddened me but I know he is no longer in pain and we can all take solace in that. I hope he is recounting some of our tales in heaven. That will bring smiles to all.


David Campbell posted on 2/11/21

Bobby was quite a salesman, he could sell ice to an Eskimo. He could also cook like a chef. I will miss him.


Germaine & Jim Hovey of Full Spectrum Retirement Plans, LLC posted on 2/9/21

We were so very sorry to hear of the sudden passing of Bobby. He was such a great guy and very encouraging to us throughout our project of renovating our office building. He was super patient and waited until we were ready for his expertise in ordering the carpet and having the best crew install it for us. And then when the "trim" painters ruined the carpet just days before we were to move in, he was more indignant and upset on our behalf than we were. We have worked with him 3 years and was looking forward to working with him again on our next project to start in about a month. We considered him a friend and are very, very sad that we won't have his encouragement and enthusiasm for our future projects. He will be missed in many, many ways.