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We are so sad about the passing of our friend Richard.  He was truly one of a kind, incredibly smart, and full of heart. Richard graduated from Miami Coral  Park High in 1967 and was not only a talented debate teacher, who impacted many lives later in life, but was also a great football player in high school.  George played along side him and those memories will always be special.  He loved his dogs, which brought him so much joy, especially his Irish Wolfhounds and Scottish Deerhound.  Richard found such happiness in life with his longtime love and wife Jen in Chicago and Madison.  We were a special part of every reunion and were lucky enough to visit them in Chicago and Madison where they built such a beautiful life together.  He will be deeply missed by all who knew him, but his intelligence, kindness, friendship and big heart will never be forgotten.  Rest in peace Richard, you made the world better just by being in it. With love & fond memories 🙏Karen and George 
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So very sorry for his loss. I was just thinking about him recently. Richard was a great person.
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I have fond memories of coaching high school debate as a colleague of  Richard's. Many of us can relate  bittersweet stories of our interactions about our travels to weekend competitions with our students. I recall Richard posting on social meeting to one of his former students just weeks ago. Richard will be truly missed!
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$2,425.00
Raised by 24 people
Serious conversation!
Serious conversation!
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— with Gary
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Richard: a gentleman’s gentleman. Richard was taken from us, we have lost a great friend. We miss the strong, generous, benevolent educator. I met Richard in high school and have remained friends for the past 65 plus years. During our school years, we would drive across the county weekly to a sports car dealership. In the showroom was always a Fiat 124 Spider on display. Richard would describe every gadget, nut, bolt and what function they performed.

Richard dedicated his professional life to sharing his vast knowledge of a variety of subjects. He was a fierce debater who spent countless hours mentoring his students and coaching them to improve their skills.

Richard lived a full, meaningful life. His legacy can be found in the accomplishments of his students. Richard always treated people with dignity and respect. He spent his personal time with his loving wife Jen (Team Leader), his Irish Wolfhounds, Scottish Deerhound, music, and sports car collection. Somehow Richard managed to fit travel into his busy schedule. He traveled as he lived, full throttle, foot on the gas pedal. Richard, carry on our dear friend. May God Bless your Soul.

Love Always,

Gary & Elaine

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Top of the State Capital Buil…
2015, Madison, WI, USA
Top of the State Capital Building — with George, Karen, Richard, Jenn and Gary
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500 ft bluff overlooking the …
2015, Pikes Peak, Iowa
500 ft bluff overlooking the upper Mississippi River — with George Russo, Richard, Gary King and Karen Russo
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What a wonderful man.  His quiet yet witty demeanor was enjoyed by all at ETHS, where we both taught.  His students especially his debaters absolutely loved him.  They soaked in his knowledge and skills.   Being a law teacher like Richard, we spent many days discussing current events such as 9/11 and the politics of the 70s to 2000s.  We also spent many days talking sports.  His Dolphins beat my Vikings in SB VIII.  We loved talking about the older players for the teams.  But we both shared the same baseball team and both got to celebrate our White Sox in 2005 -- Richard was always supporting the underdog.  

One of the funniest things was that Richard had a classroom with full length windows on the hallway side.  He never closed the blinds to those windows and anyone could peak in on him teaching classes or watch him reading a book when the students were gone.   For all those years he was truly a transparent many.  

It hurts my heart that Richard is gone.  But it is so good to remember what a wonderful person he is and always was.  

Dave Feeley ETHS 1999-2023

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Richard was a thoughtful and caring colleague.  His classroom was across from mine, and I have wonderful memories of the work he did with his students in class as well as the debate team.  We were fortunate to have had him at ETHS. 
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Dear Jennifer and Family,

I was so sad to hear about Richard's passing, he deeply affected all of our lives and I will forever be grateful to him for all that he taught me. Thinking of you, Jennifer - 

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I was deeply saddened to hear of Richard’s passing. He had such a gift for creativity, one that came alive in the books he wrote and in the way he looked at life. His love for cars was more than just a hobby—it was a part of who he was, and it added a spark to every conversation.

One of the things I’ll never forget is his go-to response whenever I asked how he was doing: “I’m adequate.” It always carried this mix of humility, humor, and quiet strength that was uniquely Richard. I’ve even caught myself using it now, and it always makes me think of him with a smile.

Please know that my heart is with you and your family during this difficult time. I hope you can find comfort in the memories of Richard’s humor, kindness, and the passions he shared so freely. He will be missed deeply, but remembered always with love.

~ Georgia & AJ 

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While only getting to know Richard recently,  he and I shared our passion for all things vintage stereo. I will always remember him as "Mr. Marantz". 
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I’m so sorry for the loss of Richard.   I had the privilege of knowing Richard for over 15 years through caring for his dogs, and I’ll always remember how much he loved them.    I loved chatting with him everyday about whatever he was working on…most recently his books, of which I will treasure my signed copies!   I would always walk in and say, “How are you today?”  His response was always, “Adequate” with a smile on his face.   Richard, you’ve always been much more than adequate to the people who loved you.   I’ll miss him dearly and feel so fortunate to have known him.   ❤️ 
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Mr. Dempsey was one of my most formative and important teachers. My condolences to his love ones. He will always be remembered fondly by his students.
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So very sorry to hear. Thinking of him and of you Jennifer. 
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Jennifer and family - My sincerest condolences for the loss of such a great man. While I didn't know Richard, I can tell I would have loved him and benefited greatly from learning from him. With love, Bre Leander
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Richard "Dempsey" Dempsey