
Herbert Leon Holleman, 73, of Manteo, NC died Thursday, May 12, 2022, at Chesapeake Regional Medical Center.
Born in Durham, NC on December 3, 1948, he was the son of the late Catherine M. Williams and Herbert Holleman.
Leon devoted his life to education. He began his career as a middle and high school teacher in Durham, NC, later becoming Assistant Principal at Southern High School, Principal at Southern Pines Middle School, and Principal of Sedgefield Junior High School in Charlotte, NC. In 1992, Leon become Assistant Superintendent of Dare County Public Schools and in 1994, he became Superintendent. After his retirement in 2000, Leon continued to serve as a Education Consultant for NERESA and often taught administration courses at East Carolina University.
An avid UNC – Chapel Hill fan, Leon enjoyed golf, travel, fishing, word puzzles, and listening to talk radio. He was an at home Jeopardy expert and stayed active in his community as a Mason and Shriner.
Leon is survived by his wife, Stephanie Fellos Holleman; two daughters, Jennifer Holleman-Smith (Danny) and Heather Holleman-Althaus (TJ); grandchildren, Zachary Smith, Allyssa Althaus, and Kayleigh Althaus; sister, Brenda Holleman (Tina); sisters-in-law, Pam Cook, Denise Fellos, Zoe F. Bell; brother-in-law, Pete Fellos; and nieces, Caroline and Austyn Holleman. Also, surviving Leon are his special dogs, Lexie and Darcy.
In addition to his parents, he joins his dog Sweet Pea in heaven.
A memorial service will be held at 1:00 pm on Thursday, May 19, 2022, at Twiford Colony Chapel.
To plant a tree in memory of Leon or send flowers to the family, please visit www.TwifordFH.com/send-flowers.
Twiford Funeral Homes, Outer Banks is assisting the family with arrangements. Condolences and memories may be shared at www.TwifordFH.com.
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Twiford Funeral Home (Outer Banks)
500 Budleigh Street, PO Box 595,
Fax: (252) 473-3392
Email: David.Jr@TwifordFH.com
Offer Condolence for the family of Herbert Leon Holleman

Benjamin Reynolds and family
There aren’t enough words for me to say how much I will miss and love this fellow. Thanks for everything Leon. I will miss you in the barbershop. Love you brother.
Lois Little Dills
Leon was one of the kindest and thoughtful classmates I have ever know. Leon we will all miss you greatly. Class of Southern High School 1967 Durham NC
George & Linda Pearce, Manteo, NC
Sending our sympathy to Leon’s family and many friends.
Wanda Gardner Rhoden
Leon definitely leaves a void in the lives of all who knew him. He certainly has left avoid in the lives of his fellow SHS Class of ‘67. My condolences to, and prayers for his family.
Faye Lewark Daniels
My thoughts are with you and your family at this time; may your memories bring you comfort.
“Perhaps they are not stars, but rather openings in heaven where the love of our lost ones pours through and shines down upon us to let us know they are happy.” ~~ Eskimo Proverb
Ruth & David Collins
Our heartfelt thoughts and prayers for family and friends! Leon was a treasure to all who knew him. We were classmates at SHS Class of 1967. Cherish your memories!
Jean Taylor
Stephanie and family,
I am so sorry for your loss. God bless you and keep you during this time.
Jean Taylor
Pam and John Buscemi
We were so saddened to hear of Leon’s passing and offer our deepest sympathies to Stephanie and all the family. May God surround each of you with his love and comfort you with his peace.
Glenda D Holleman
Leon was a very kind and loving man. He will be missed by his 1967 classmates and all those who had the pleasure of knowing Leon. RIP
Tom Bowen
Mr. Holleman was a gifted teacher and touched the lives of many kids in Durham NC . His memory will live on forever. Thoughts and prayer for his family.
Mitchell Bateman
I worked for Leon the entire time he was here in Dare County Schools. He was a blessing to work for and one of few leaders I’ve ever known who had the unique gift of making you want to follow instead of demanding that you follow. Leon was my boss but most of all my friend. He understood people and made decisions in his job here that were in the best interest of people, not just the machinery of education. Leon will always have my upmost praise and respect. I loved him and will miss him. My prayers for his family as we all mourn his loss.
God speed my friend !!
Patty Callum
I am so so sorry to hear the news. Thanks for all the laughs through the years. I never got a chance to buy you that round. Sending many condolences to Stephanie and Girls. You will be missed.
Claudia C Twiford
Words cannot express the loss that will be felt by Northeastern NC with the passing of Dr. Leon Holleman. “Doc”, as known by His family and friends, was an advocate for excellence in education for the students and teachers. Loving thoughts and prayers for his family!
Claudia Twiford
Lisa Stickley
My thoughts and prayers are with the entire family at this sad time. Leon was a very special person to all of us in the educational setting in CMS and will be missed by so many people. All my love to Stephanie and his family and RIP my dear friend❤️
Dr. Michael Dunsmore
Leon was a wonderful colleague, mentor and friend. He was always there for me. He will be missed. Our prayers are with Stephanie and the family.
Mike and Diane Dunsmore
Charlie Holleman & Betty Sanders
A fine gentleman has gone to be with his Lord and Savior Jesus Christ . We who are left here will surely miss Leon, his funny stories, his great sense of humor, and his words of wisdom. May we all remember his family and friends as he would certainly want us to do. Rest In peace cuz.
Ron Rowe SHS 1967
Brilliant, kind, compassionate, thoughtful, a genuine leader and loved by all. Leon made a positive difference in so many people . He will be greatly missed .
Derek Hampson
When I first started teaching in Durham, Leon was a teaching coach, and quickly became a kindred spirit. The humor, the intelligence, and the love of students was paramount. Having the pleasure of teaching with his Daughter and now his Granddaughter, I feel ever so blessed to have met him. Your spirit is with us, your body’s atoms will recycle into the biosphere and contribute to the lives of those to come, and your memory will live on. Thanks for being a friend.
Carol Coujcil
Leon introduced me to my husband on a blind date. I will forever be in his debt!
For nearly 50 years Leon has been a friend, a good memories cohort, and part of our
Lives in thought if not in daily contact. “Remember when Leon…..” will be a part of us forever.
Carol council
Arty and Pam Tillett
Stephanie and family,
So sorry to hear of Leon’s passing. He will be greatly missed. Please know that you are in our thoughts and prayers.
Arty and Pam
Holly Meekins Williams
Sincere sympathies to the Holleman family.
Kathy Repko and Andy Smith
Leon- Doc- was ever a dear friend and colleague. Your family is in our hearts. And the fondest of memories are in ours. May love sustain you.
Gene Gallelli
We have lost a brilliant educational visionary and a compassionate, loving, husband, father, grandfather and friend. Leon could talk to anyone and leave them laughing, smiling, and better informed. He has earned his place among the brightest stars in the evening sky and will be missed by the endless parade of those who loved him. Rest In Peace dear friend and partner.
Laura dough
So grateful I had him for a boss. Always kind to me and understanding of my job. Good man who had an open door policy and always approachable. Deepest sympathy to his family .
Pat Taylor
Stephanie and family,
I am so sorry to hear of Leon’s passing. He was a good and fair man. Keeping you in my prayers for peace and strength.