Mr. James "Jimmy" Madison Bailey II

James Madison Bailey II – beloved husband, father, grandfather, brother, cousin, mentor and friend to all who knew him – passed away peacefully in his home, surrounded by family, on Monday, July 21, following a brave battle with cancer. He was 82.

Known to those who loved him as Jimmy, Dad, Papa, Coach, Tubby, “Unc” or Uncle Jimmy, and Baby Boy, he lived his life with contagious optimism and a strong devotion to faith, family, Aggie football, high school sports and a lifelong motto: “If it is to be, it’s up to me.”

A dedicated Catholic servant and mentor, Jim was truly at his happiest around people. Family, friendships and an honest day’s work fueled a larger-than-life personality that inspired all, whether cheering on those he loved, celebrating milestones or coaching generations of high school football teams across South Texas.

A storyteller and jokester, Jim always appreciated a good laugh and dished out one-liners with ease. His sense of adventure and passion for games, golf, cruising, movies and sweets was surpassed only by an enduring love for his wife of 55 years, Diane, four children and eight grandchildren. He found great joy in watching them all succeed, and the daily texts from Papa will never be forgotten.

As an older brother, Jim provided a never-ending source of unconditional love and support. As a friend, Jim remained loyal and generous, with many of his closest companions considering him a brother. It was often said that he never met a stranger and left everyone he met standing a little taller, breathing easier and feeling like they mattered. He tackled challenges with the courage, humility and strength of a leader.

The eldest son of a homemaker and a salesman/Army veteran, Jim was born and raised primarily in San Antonio, where he attended St. Gerard Catholic School and spent many days with his grandfather exploring the family’s ranch near Blanco, Tx. His family moved to Corpus Christi in 1952, where he attended St. Patrick Catholic School and Sundeen Junior High before graduating from Mary Carroll High School in 1960. Six years later, he proudly graduated from Texas A&M University (Whoop!) with a Bachelor of Science in physical education, and earned a Master’s in Education from Our Lady of the Lake University in 1978.

Jim’s coaching career spanned 32 years and nine schools across South Texas, leaving an indelible mark on those he taught in football, track and basketball. Starting his career in 1966 at Nimitz Middle School in San Antonio, Jim later joined the coaching staffs of San Antonio Lee, Kerrville Tivy, Brownsville Hanna, Laredo Martin and San Antonio Edison high schools before rising to be head coach and/or athletic director at Freer (TX), Antonian, South San and Jefferson high schools. He developed an expertise in offensive line and quarterback coaching, touching the lives of generations of players who went on to college, coaching or professional life, and even the NFL. For the rest of his life, he mentored and stayed connected to many of the coaches and players he knew – truly special connections that meant the world to him. He retired from coaching in 2004.

As a second career, Jim also touched the lives of many as a realtor and broker, delivering peach trees to proud new homeowners and leading one of the largest Century 21 offices in San Antonio in the late 1980s. His legacy as a loving, selfless family man and friend will live on in all who knew him.

Jim is preceded in death by his parents, James Madison Bailey and Marguerite Louise Calmbach. He is survived by his loving wife, Mary Diane; daughters Brenda Lutz, Teri (Abe) Levy and Wendy (Chris) Kirchoff; son James M. “Trey” (Sherri) Bailey III; eight grandchildren, Lyndsey and Sydney Lutz; Corinne, Joshua and Landon Levy; Max Bailey; and William and Chase Kirchoff; sister Christina “Chrissy” (Mike) Smith, and nephews Lance (Karen) FitzSimon, Drew FitzSimon, and dozens of beloved first, second and third cousins.

A visitation will be held from 5:00 p.m. to 7:00 p.m., with a Rosary to follow at 7:00 p.m., on Tuesday, August 5, 2025, at Porter Loring Mortuary North, 2102 N. Loop 1604, San Antonio, TX 78212.

A Funeral Mass will be held at 10:00 a.m. on Wednesday, August 6, 2025, at St. Helena Catholic Church, 14714 Edgemont St, San Antonio, TX 78247.