Jackie Craghead at the 2023 Classique Gala, where her signature flair shone through a whimsical tablescape adorned with her beloved hat collection—a joyful nod to her style, creativity, and enduring sparkle.
Jackie Craghead was more than a volunteer, more than a leader—she was a force of joy.
September 9, 1941 – September 2, 2025
With her radiant smile, quick wit, and impeccable sense of style, Jackie made every room brighter, every event more magical, and every cause more unforgettable. Her passing leaves an ache, but her spirit will forever be celebrated in the community she so passionately served.
Jackie’s journey began in Homewood, Alabama, where her natural compassion revealed itself early as she helped homebound neighbors with groceries and chores. That heart for service became her compass as life took her across the globe as an Army officer’s wife, raising three children in Germany and traveling through Paris, Rome, Venice, and beyond. When she settled on the Monterey Peninsula, she found the community she would call home for the rest of her life—and the stage for her extraordinary legacy
Jackie didn’t just live in Monterey County—she transformed it.
It was here that Jackie met Don, the love of her life for more than 40 years. Their story began with a spark in a jewelry shop, where Don spotted Jackie admiring a ring and declared to his co-worker, “I’ll take this one.” From that moment, their partnership flourished in laughter, adventure, and five years of ballroom dance lessons that kept them gliding across dance floors for decades. Together, they embodied love in motion.
Jackie’s voice and presence were as powerful as her vision. At the First Baptist Church of Pacific Grove, she lifted her voice in the choir and delighted in sharing the church’s proud history as the oldest African-American congregation on the Central Coast. She was equally at home in civic halls and gala ballrooms, serving as president of the NAACP, guiding The Links, Inc., or welcoming international officers through the Naval Postgraduate School’s host program. Whether leading meetings or hosting guests, Jackie brought elegance, warmth, and her signature sparkle.
Service with sparkle—that was Jackie’s gift.
Her creative flair was unmatched. For 26 years, she dazzled guests at MOWMP’s Classique Gala with table designs that were works of art—extravagant, whimsical, and always conversation-stopping.
She transformed fundraisers for The Salvation Army, La Merienda, Pacific Repertory Theatre, and countless others, proving that fundraising could be both impactful and unforgettable. Jackie didn’t just decorate tables; she created experiences that made people feel joy, generosity, and belonging.
She didn’t just decorate tables—she created moments that became memories.
The accolades poured in, and rightfully so: Outstanding Woman of Monterey County, MOWMP Women Who Care, NAACP President’s Award, Quota Club Woman of the Year. Yet Jackie wore her honors lightly. Recognition never drove her—it was her love for people, her commitment to community, and her joy in bringing others together that fueled her tireless service
Jackie was not simply a volunteer or board member—she was the heart behind the cause, the sparkle at the gala, the steady hand behind decades of community progress. She showed us all that service could be joyful, that leadership could be graceful, and that beauty could live in both artful tablescapes and heartfelt acts of kindness.
Jackie was the sparkle at every gala, the warmth in every gathering, and the voice of joy in every choir.
Jackie Craghead lived her life as a celebration, and her legacy will continue to inspire. Monterey will remember her not just for what she did, but for how she made us feel: uplifted, joyful, and deeply connected.
She was preceded in death by her son, Courtney Mathis, and one of her daughters, Felicia (Lisa) Trosky. She is survived by her husband, Donald; daughter, Sonia Ramirez (Tony); granddaughters, Tiffany Riley, Jennifer Louis and Jazmine Ramirez; five greatgrandchildren and son-in-law, Lynn Trosky.
Additional affiliations (approx. dates)
- Meals on Wheels of the Monterey Peninsula, board of directors, 1982 to 1985, 2007-2022
- Pacific Repertory Theatre, board of directors, 1994 to 2000
- Community Foundation’s Neighborhood Grants Program Committee
- Monterey County Red Cross, board of directors, 1992 to 1998. Various committee chairs, including Red Cross Ball chair
- Carmel Music Society, board of directors, 1988 to 1996
- Lifesavers (youth suicide prevention), committee member, 1992 to 1995
- YWCA, board of directors
- Various committee work for many organizations as needed
- Visiting Nurse Association, foundation board and nomination committee chair
- American Heart Association, Go Red For Women Luncheon Committee, Power To End Stroke Committee
- Naval Postgraduate School, DRMI community host for foreign officers
- Monterey Civic Club, three term president, past vice president
- Dance Kids, Inc.; board of directors, 2000 to 2006
- Community of Caring, board member and special events co-chair
- Ventana Wildlife Society, Condor Release Fundraiser, committee member
- Edith Alt Friendship Circle, coordinator
- Planning Commission, City of Seaside 1984 to 2010, chairperson, 1999 to 2003
- National Association for the Advancement of Colored People, Monterey Peninsula Branch (NAACP); Golden Heritage member, past executive committee member, offices held: 3rd V.P., 2nd V.P., 1st V.P., and two terms as president, 1990-1994.
- Monterey Bay Symphony, board of directors, 1998 to 2010
