A Life of Service, Love, and Faith
John Edward Rolley, Jr. was born on July 11, 1949, in Crisfield, MD, to John Edward Rolley, Sr. and Naomi Francis. On Thursday, October 1, 2026, God called John peacefully home, leaving behind a legacy of faith, service, and love for his family.
John graduated from Carter G. Woodson High School in 1967. In 1971, he married Cynthia, the love of his life. He proudly served 17 years in the United States Air Force, with overseas assignments in Guam, Hawaii, England, and Kuwait during Operation Desert Storm. His remarkable knowledge of aircraft carried him into a second career with Lockheed Martin as an aviation mechanic.
John took great pride in his military service, particularly his work maintaining and troubleshooting C-130 aircraft. He enjoyed sharing stories about the repairs he performed and the conversations he had with pilots as he helped them troubleshoot mechanical problems in flight. When he wasn’t talking about airplanes, John was enjoying his music. Old-school R&B was his favorite hobby and the soundtrack of his life. Whether at home, in the car, or with family and friends, the classics were always playing, and he loved sharing the songs that meant so much to him with everyone around him.
Beyond his accomplishments, John was a faithful husband, loving father, proud grandfather and great-grandfather, caring brother, and treasured friend. He found joy in sharing stories, offering encouragement, and spending time with those he loved.
From the beginning, Cynthia stood by John’s side, caring for him day in and day out and ensuring he never lacked her love and support. But their relationship was so much more than caregiving. They were companions and best friends who shared life’s everyday moments. Wherever you saw Cynthia, you knew John was never far behind, or he was waiting patiently in the car! Their bond was a beautiful testament to 55 years of love and friendship.
John leaves to cherish his precious memories with his loving wife of 55 years, Cynthia Rolley, and their four children; his daughter, Dionne Stum, and her children, Ebony, Zion, Xavier, and Genesis; his son, John Edward Rolley III, his wife, Tannesia, and their children, Jaida and John Edward Rolley IV; his daughter, DeCember Bodine, her husband, Steven Bodine Jr., and their children, Isys, Steven III, and Wynter; his son, Michael Rolley, and his children, Michael Jr., Annaliece, and De’Lynn; he also leaves 12 grandchildren and five great-grandchildren, who will carry forward the family legacy he helped build.
John is also survived by his siblings, with whom he shared a special bond; his loving sisters, the Reverend Joyce Whittington and Carolyn and Russell Bates, and his brother, Vance Rolley; his very special friends, Raymond Coxen; Bowser Jones and Julia Rolley; and a host of beloved nieces, nephews, extended family, and dear friends, all of whom were blessed by his kindness, humor, and friendship.
John was preceded in death by his parents, John Edward Rolley Sr. and Naomi Francis; his sisters, Janet Weatherbe and Kaye Jones; and his brother, Lowell Anthony Rolley.
John will be remembered for his dedication to his country, his love for his family, his sense of humor, and the special way he touched the lives of those around him. His earthly journey has ended, but the love he shared, the lessons he taught, and the memories he made will remain in our hearts forever.
Rest peacefully, John. Your service is complete, your work is done, and your legacy lives on through the generations you leave behind.
A Funeral Service will be held 1:00 PM Saturday, October 17, 2026, at Anthony E. Ward, Jr. Funeral Home, 30539 Hampden Avenue, Princess Anne, Maryland with a viewing one-hour prior. A public viewing will be held 2:00 PM-6:00 PM Friday, October 16, 2026, at the Funeral Home.
3 Responses
To My Daddy in Heaven 💛
Daddy, you taught me so many lessons throughout my life. Some I understood right away, and some took me years to truly appreciate. But if I had to choose the lessons that have shaped me the most, these four would be at the top of my list:
1. “If you’re going to do something, do it right the first time so you don’t have to do it over again.”
You taught me to take pride in what I do, to put my whole heart into it, and to give it 110% the first time around. No cutting corners. No doing things halfway.
And Daddy, you already know… no half-assing over here! 😂💛
2. “Haste makes waste.”
This one taught me patience. It taught me to slow down, think things through, and not allow the urgency of a moment to make my decisions for me.
Looking back now, I realize you and Mom were teaching me something even bigger: move with intention, honor, respect, and integrity.
3. “Be yourself.”
This one took me the longest to truly understand.
For so much of my life, I worried about what society considered “normal.” I tried to fit into boxes that were never really made for me.
But I finally understand…
I am different. And that’s okay ✨️💛✨️
Different doesn’t mean wrong. It doesn’t mean I need to shrink myself or become someone else to fit in.
It means I’m me ♡
And Daddy, I think I’m finally learning to embrace that 🥹
4. You taught me STRENGTH 💪🏾
I watched you survive and recover from so many incidents, struggles, and traumatic accidents throughout your life. I watched you get knocked down and somehow find a way to keep getting back up. Our literal humpty dumpty ❤️
You taught me that strength isn’t the absence of pain. Strength is deciding not to give up despite the pain.
You taught me that as long as I have breath in my body, I keep going.
And I know there will be days when life knocks the wind out of me. There will be days when I don’t understand why something happened or wonder how I’m supposed to keep moving forward.
But Daddy, I’ll remember you ✨️💛✨️
I’ll remember that stubbornness of yours 😂
I’ll remember your strength.
I’ll remember your lessons.
And I’ll remember that as long as there is breath in this body, I won’t give up.
You left me more than memories.
You left me pieces of yourself.
The way I work.
The way I love.
The way I serve others.
The way I stand back up.
The way I keep going.
And especially that part of me that’s stubborn as hell too 😂💛
I am your daughter, and I carry you with me in more ways than I could ever explain 💞
I love you, Daddy ~ Forever Daddy’s Girl
So saddened😢 to hear of the passing of my classmate, John Rolley. John had a quiet and gentle spirit, light humor “sometimes”. Very kind person. John liked to tease me a little about what boys I liked!!!-sometimes he was right 😂-I will always remember his kind and gentle spirit. Praying for Cynthia, yes the love of his life , his children, grands and great grands and the entire Rolley family ..
With Sorrow
Shellie Whittington-Jones
Class of 1967
Carter G Woodson School
Sending my most heartfelt condolences to the family during this your time of sorrow. Remembering John as we all roamed the halls of Carter G. Woodson High School. His quite and gentle demeanor is what I remember most. My prayer for all of you is may our Lord Jesus the Christ wrap his loving arms around you all to bring you comfort during this your time of sorrow. PEACE AND GRACE. Rev.Stetson Elroy Lane Jr and the Enon Baptist church Of Deliverance Church Family Crisfield Maryland.