Cheever, Benny Leonard's Obituary
The Cheever family is heartbroken to announce the passing of Ben Cheever on Memorial Day, May 25, 2026. Ben suffered a catastrophic aneurysm on Saturday, May 23, and despite the efforts of his medical team at Peninsula Hospital, passed away surrounded by the love of his family.
Ben was the heart and soul of his family, while his wife Elyse was always the glue that held it together. His life can best be described by three enduring principles: service, perseverance, and an unwavering devotion to the people he loved. He was a compassionate, generous, and deeply loyal man whose greatest gift was simply being there for others.
Ben's commitment to service began at the age of 17 when he enlisted in the United States Army and was sent to Vietnam. Though trained in logistics, he was assigned to combat operations with a Special Forces unit, where he rose to the rank of Sergeant and earned the Bronze Star. His military service profoundly shaped his character, strengthening the sense of duty, resilience, and service that would guide the rest of his life.
After leaving the Army, Ben became a San Mateo County Sheriff's Deputy. It was during this chapter of his life that he met the love of his life, Elyse. After the birth of his sons, Ethan and Ephraim, he chose a path that allowed him to focus more fully on family and began a long career in the airline industry.
No matter where life took him, Ben made it a priority to show up for the people he cared about. He attended countless meetings, sporting events, school functions, classes, performances, and celebrations. He regularly attended religious services alongside Elyse, a Cantor in the local Jewish community, and embraced opportunities to support the people and organizations that mattered to his family.
When his sons became involved in Cub Scouts, Ben founded Cub Scout Pack 355 so he could spend more time with them and help create meaningful experiences for other families as well. As the boys grew older, he became deeply involved with Boy Scout Troop 355, eventually serving as one of its longest-tenured Scoutmasters. He mentored generations of young men, helping many—including his own sons—earn the rank of Eagle Scout. Scouting became a central part of family life, and Ben took his responsibility to the youth of the troop and the City of Millbrae seriously. He believed that leadership was not about recognition, but about service, guidance, and showing up when people needed you.
After retiring from the airline industry following a serious injury, Ben embraced a new challenge by returning to school. He earned both his bachelor's and master's degrees while continuing his lifelong commitment to learning and service. He volunteered at schools where Elyse taught and remained actively involved in his community. Later, he became a Freemason alongside his sons at the Burlingame Masonic Lodge and continued his service through the Masonic fraternity and Scottish Rite organizations.
Ben enthusiastically supported both of his sons in their careers and entrepreneurial ventures. He took genuine interest in their work and found joy in helping them succeed. Many of their professional pursuits reflected interests he had nurtured throughout his own life, including history, aviation, entrepreneurship, real estate, and personal protection.
Ten years ago, Ben overcame cancer. Even as his health challenges increased over the years, his spirit never diminished. He remained engaged, optimistic, and devoted to helping his family and supporting the organizations and communities he loved.
Becoming a grandfather brought Ben immense joy. He eagerly awaited the birth of each grandchild, supported his growing family whenever needed, and rarely missed a field trip, performance, game, presentation, or milestone. His grandchildren knew him as a constant presence in their lives, just as his sons had. Whether someone needed advice, encouragement, childcare, an extra set of hands, or simply someone to share an experience with, Ben was there.
To his sons, he was a hero to aspire to, a trusted advisor, a wise elder, a travel companion, a model parent, and a pillar of strength. To his wife, he was a devoted partner. To his grandchildren, he was a constant source of love and support. To countless scouts, friends, colleagues, and community members, he was a mentor whose example left a lasting impression.
Ben never fully realized the profound impact he had on the lives of those around him. Through his service, mentorship, kindness, and unwavering devotion to family, he leaves behind a legacy that will endure for generations. The measure of his life is not only found in his accomplishments, but in the countless people whose lives were better because he chose to be present, to help, and to care.
Ben is survived by his beloved wife, Elyse; his sons, Ethan and Ephraim; their spouses; his cherished grandchildren; and a large extended family and community of friends whose lives he touched deeply.
His funeral and internment will be held at Skylawn Memorial Park on Sunday, May 31, 2026, at 11:30 a.m., followed by a reception and time of memory sharing at the Burlingame Masonic Lodge at 2:30 p.m.
Men like Ben are rare. He will be deeply missed and lovingly remembered.
May his memory forever be a blessing.
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