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Richard Stephenson Obituary

Stephenson Jr., Dr. Richard Earl Former CPS Superintendent, Richard E. Stephenson, Jr., born June 4, 1929 in Nashville, Tennessee passed away quietly at his Hyde Park home after a long illness on November 12. He attended Pearl High School in Nashville along with future wife, Ruby Jordan, prior to enrolling at Tennessee State University where he earned a Bachelor's degree in Natural Sciences and joined Alpha Phi Alpha fraternity. After college, he was drafted and served as Artillery and Guided Missile Officer during the Korean War. After honorable discharge, Lieutenant Stephenson and family moved to Chicago where he worked as research assistant at Illinois Research at University of Illinois. In 1958, Richard embarked on a career with CPS starting as science teacher, disciplinarian, Assistant Principal and Principal at Forrestville Upper Grade Center in Bronzeville. He was manager of Little League baseball teams and served as President of Chatham Village Neighborhood Association. He subsequently became Principal at Dunbar Vocational High School where he fiercely advocated for vocational education. He earned a Master's degree in Education from University of Chicago and Educational Doctorate from Southeastern Nova University. He became Interim Superintendent of CPS from which he retired in 1993 after 35 years of dedicated service. It was always about the kids. Dr. Stephenson was an accomplished musician, jazz pianist and singer, performing for many years, most recently with the Kindred Souls, a group of musician/educators who played at many social functions. He represented Chicago as Vice President of Illinois High School Athletic Association Board of Directors and was honored as Outstanding Alumnus of Tennessee State University. Richard joins a sister, Vendolyn (2016) (William Harris), and son, H. David (2012), and is survived by his wife of 68 years, Ruby; daughter, Lynn Allen; two sons, Richard III (Susan) and George; sisters, Barbara Boyd and Odessa Miller; nine grandchildren; two great-grandchildren; many cousins, nieces and nephews. A memorial service will be held on Saturday, December 8th with visitation from 9:30 to 10:30 a.m. and services to follow from 10:30 a.m. to 12:00 p.m. at St. Mark's Methodist Church at 8441 S. St. Lawrence in Chicago.

To plant trees in memory, please visit the Sympathy Store.

Published by Chicago Sun-Times on Dec. 2, 2018.

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Frank C. Logan

April 20, 2025

I was just thirteen when I met Dr. Richard E. Stephenson, Jr.—but he carried the weight and wisdom of generations. He wasn’t just the principal of Dunbar Vocational High School during my time there—he was the presence that shaped what I believed a Black man in leadership could look like.

I believe he spoke three languages. French and English for sure, and if I recall correctly, Spanish as well. But the first language he ever spoke to me was respect. He carried himself with what I can only describe as “power under control.” Professional. Kind. Cool. Always sharp—always present.

He taught me the soul-brother handshake, and I still shake hands that way today. Not out of habit, but out of heritage. Because that moment wasn’t just about greeting—it was about identity, connection, and shared pride.

Dr. Stephenson encouraged us ceaselessly—not with hype, but with high expectations and a belief in our worth. He wasn’t just seen in the halls. He was felt—his presence told us we mattered. That education mattered. That we mattered.

If—and when—it becomes my turn to stand in that kind of role, to lead a school and hold space for others the way he held space for us, I pray to bring even half the measure of grace, brilliance, and strength he brought into every room.

If I can do that, I will feel truly accomplished—not just as an educator, but as a man. I thank him for modeling manhood for me.

Frank C. Logan
DVHS - Class of 1991.

Sharon J. Dumas Byron

December 19, 2018

Mr. Stephenson was my 6th Grade Science teacher (1960) at Forrestville South Elementary School. He was a dedicated teacher who held high expectations for all his students. Mr. Stephenson inspired me to enter the field of education and after graduation I visited him when he was principal at Dunbar High School. A few years later I was driving down Beverly Avenue and pulled over when I saw Mr. Stephenson standing in front of his garage. He invited me inside his home, introduced me to his beautiful wife and asked me to play a song on his piano. I learned early today of the demise of Mr. Stephenson and know that he is singing and playing his piano with the angels in heaven. Thank you for your guidance, love and contribution to education.

Mary Rush

December 8, 2018

When the Board of Education transferred me to Dunbar High School during faculty desegregation, I walked into the Main Office at Dunbar, extended my hand to you, and declared facetiously that I was there under protest. I had been transferred to Dunbar from my alma mater and Dunbar's arch rival, Wendell Phillips High School. You smiled and told me I would come to love Dunbar. You were right! I did, even though I loved Phillips more. I enjoyed being a member of your Business Department. Dr. Stephenson, you "dun good." Mary Rush

Sincere Serenity

Glenda Singleton-Beal

Sent Flowers

Ocean Breeze Spray

a loved one

Sent Flowers

Lee Jones

December 4, 2018

Thank You Dr. Stephenson for your leadership, dedication, discipline, and inspiration. To the Stephenson family may God continue to bless you. Class of 1983

Marilyn Brazil-Anderson

December 4, 2018

I wish to express my sincere condolences to my friend, Ruby and the rest of the Stephenson family. You were blessed with a truly brilliant and talented husband and father. May he Rest In Peace. Sincerely, Marilyn Brazil-Anderson

Z L

December 4, 2018

My sincere condolences to your family for the loss of your love one. May the God of comfort be with you during this sad occasion and may his loving words at John 6:40 console your heart.

Nathaniel Dickson

December 3, 2018

A wonderful educator and friend. He was always there for the students and staff. His legacy will be lasting, as principal at Dunbar H.S. May he rest in peace.

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Memorial Events
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Dec

8

Memorial service

9:30 a.m. - 10:30 a.m.

St. Mark's Methodist Church

8441 S. St. Lawrence, Chicago, IL

Dec

8

Service

10:30 a.m. - 12:00 p.m.

St. Mark's Methodist Church

8441 S. St. Lawrence, Chicago, IL

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