News Summary
James Madison Bailey II, a cherished coach and mentor in South Texas sports, passed away after battling cancer. Known for his dedication to education and athletics, he shaped countless young athletes’ lives. His passion for coaching, particularly in football, left a lasting impact, and he is remembered for his infectious optimism and commitment to family and community. A memorial service will celebrate his life and legacy.
San Antonio, Texas – James Madison Bailey II, a beloved figure in the South Texas sports community, passed away peacefully at home on July 21, 2025, at the age of 82 following a courageous battle with cancer. Known affectionately by friends and family as Jimmy, Dad, Papa, Coach, Tubby, and Uncle Jimmy, he spent his life nurturing a deep devotion to his faith, family, and the world of athletics, particularly his passion for Aggie football and high school sports.
Bailey’s legacy is marked by his infectious optimism and a guiding principle: “If it is to be, it’s up to me.” His commitment to coaching and mentoring extended over three decades, during which he shaped the lives of countless young athletes across multiple schools in South Texas. He began his coaching career at Nimitz Middle School in San Antonio in 1966 and went on to serve as head coach and athletic director at several institutions, including Freer, Antonian, South San, and Jefferson high schools.
Throughout his coaching tenure, Bailey focused primarily on developing offensive lines and quarterbacks, and his influence helped many players advance to collegiate levels, coaching positions, and even the NFL. Despite retiring from coaching in 2004, he maintained lasting relationships with former players and fellow coaches, signifying the profound impact he had on their lives.
Personal Life and Family
Born in San Antonio to James Madison Bailey and Marguerite Louise Calmbach, Jim grew up steeped in rich family traditions. He attended St. Gerard Catholic School and spent significant time at his grandfather’s ranch near Blanco, Texas. In 1952, he moved to Corpus Christi, progressing through St. Patrick Catholic School and Sundeen Junior High before graduating from Mary Carroll High School in 1960.
Bailey obtained a Bachelor of Science in physical education from Texas A&M University in 1966, followed by a Master’s in Education from Our Lady of the Lake University in 1978. He married his lifelong partner, Mary Diane, and together they nurtured a family of four daughters and one son, along with eight grandchildren. His role as a father and grandfather brought him immense joy, and he remained actively engaged in their lives, celebrating their milestones and successes.
A Multifaceted Career
In addition to coaching, Bailey had a successful career as a realtor and broker, operating one of the largest Century 21 offices in San Antonio during the late 1980s. This multifaceted career showcased his adaptability and the extent of his involvement in the community.
Bailey was known not just for his coaching talent, but also for his vivid personality. He brought humor and joy to those around him through storytelling and light-hearted jokes. His vibrant spirit resonated well beyond the football field, as he values relationships and community engagement deeply, which made him a cherished mentor and friend.
Community Tribute
The profound loss of James Madison Bailey II has been felt across the South Texas community. His contributions to education and athletics will be remembered and celebrated by the many lives he touched. A visitation and Rosary are planned for August 5, 2025, with a Funeral Mass scheduled for August 6, 2025, at St. Helena Catholic Church in San Antonio, allowing friends, family, and former players to pay their respects and honor his memory.
Jim Bailey is survived by his wife, Mary Diane, his four children, and eight grandchildren, alongside a large extended family that includes his sister, Christina “Chrissy” Smith, and several nephews. His legacy continues through the values he instilled in those he mentored, which will resonate for generations to come.
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Additional Resources
- Dignity Memorial: James “Jimmy” Bailey
- Wikipedia: James Bailey
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- San Antonio Magazine: Top Doctors 2021
- Google News: San Antonio Top Doctors
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