In Loving Memory of Pennie Jeanine Chesser
August 11 1956 – November 3, 2026
Pennie Jeanine Chesser, 70, passed away on November 3, 2026, leaving behind a family who loved her deeply and memories that will last a lifetime.
Pennie was a kind and loving woman with a strong personality, a heart of gold, and a spirit that was impossible to forget. She was strong-willed, outspoken, and never afraid to speak her mind. She could be a hard ass when she needed to be, but beneath that tough exterior was a mother whose love for her family knew absolutely no limits.
Her children were her world. She dedicated her life to taking care of them, standing beside them, and making sure they always had someone in their corner. No matter what life threw their way, Pennie was there. Whether it meant bailing them out of a difficult situation, picking up the pieces, offering advice, or simply being the person they could always count on, she never stopped showing up. She gave endlessly, often putting the needs of her children before her own.
Her love extended beyond motherhood. She stepped in and raised her granddaughter when her daughter was unable to do so, giving her the love, care, and presence that only Pennie could give. That was simply who she was. When someone she loved needed her, she showed up.
Pennie had a love for the simple things that made life beautiful. She loved being outdoors, tending to her garden, and surrounding herself with the things that brought her happiness. Music was another one of her great loves, especially the blues. She enjoyed going to concerts with her best friend, Valerie Gray, making memories and sharing moments that will be cherished forever.
And then there was her laugh. Pennie had the most contagious laugh, a real, hearty, from-the-belly laugh that could fill a room and make everyone around her smile. It was unmistakably hers, just like her personality. She affectionately called her daughter her "Pinky’a special little name that will forever hold a place in her heart It's the kind of memory that will bring smiles through the tears and remind everyone just how much of her lives on in the little things.
Pennie leaves behind a legacy of unconditional love, strength, sacrifice, laughter, and devotion to family. She wasn't perfect, and she never pretended to be. She was simply Pennie: tough, loving, protective, funny, and one of a kind.
She is survived by her two children, Angela Chesser and Paul Chesser; her mother, Ivanelle Chesser Ridgway; her sister, Laura Shepherd niece, Kazmira, McCarthy, and her beloved granddaughter, Liam Whitteker.
Though her passing leaves an unimaginable emptiness in the hearts of those who loved her, her laughter, her love of music, her gardens, her strength, and the countless ways she showed up for her family will never be forgotten.
A mother's love doesn't end when her life does. It lives on in the children she raised, the grandchildren she loved, the laughter she shared, and the memories that will forever bloom in the hearts of those she leaves behind.
Rest peacefully, Pennie. Keep the music playing. You will forever be loved, missed, and remembered.
Forever our Pennie
Pennie also dedicated a part of her life to caring for others through her work at Hillmont Psychiatric Center, where she served as a Placement Coordinator and worked on the floor as a nurse, caring for individuals experiencing mental health challenges. Her work reflected another side of the woman she was: someone who understood the importance of showing up for people, looking after those in need, and making a difference in the lives of others. Caring for people wasn't just something she did for her family; it was also part of the work she devoted herself to.
Family and friends are invited to Graveside Funeral Services Friday November 13, 2026 at 2:00pm at Ivy Lawn Cemetery, Ventura. Arrangements are under the direction of the BOYKO & REARDON TELEGRAPH ROAD MORTUARY & CREMATION, Ventura.