Rupert "Cabby" Caballero

Rupert "Cabby" Caballero, 94, of Waukon, IA, died Monday, December 16, 2024, at Thornton Manor in Lansing, IA. Memorial services will be held Saturday, December 21st, at 10:00 AM at St. Patrick Catholic Church in Waukon, with Fr. Joseph Sevcik officiating and military honors to follow. Friends may greet the family from 4:00 PM - 6:00 PM Friday at Martin - Grau Funeral Home in Waukon, where there will be a 3:30 PM scripture service. The service will also be live streamed on the church's facebook page: www.facebook.com/stpatswaukon

Rupert "Cabby" Caballero was born on March 27, 1930 in Oelwein, IA, to Braulio "Mike" and Anita (Ramirez) Caballero. He was baptized and confirmed at Sacred Heart Catholic Church in Oelwein. Rupert graduated from Oelwein High School in 1948.

After graduation, Rupert entered the United States Marine Corps, where he proudly served from 1948-1952, earning a purple heart during the Korean Conflict. During part of his time in the Marines, Rupert was a drill instructor, where he learned he loved educating others. Rupert earned his BA from Upper Iowa University and his Masters from the University of Iowa. He spent a lifetime as a coach, teacher, or principal influencing the lives of countless youth across Iowa.

While in college Rupert met the love of his life, Martha Ruth Miller, and they married in 1956. Together they raised two daughters. Family was always a priority and most weekends included a trip to Oelwein to spend time with the Caballero crew. Rupert liked golfing, fishing, hunting, and gardening. He was a member of the VFW Post 4117, Honor Guard, and Waukon Golf and Country Club. He also served on the Allamakee County Fair Board. After retirement, Rupert and Martha wintered in Apache Junction, AZ, for many years. Rupert embodied the spirit of living life to the fullest and the philosophy that it is better to look forward than to look back.

Survivors include his wife Martha; his daughters: Karen (Dave) Mathis and Carol (Chris) Lilly; grandchildren: Mara (Casey Bode) Mathis, Brooke (Wild) Mathis, Jake (Morgan) Lilly, and Josh Lilly; great-grandchildren: Wava and Weller Mathis, Rhealee Dickens, and Charli Bode. Rupert is also survived by his sister Angie Alveraz, brother Mike (Coke) Caballero, and many nieces and nephews.

He was preceded in death by his parents Anita and Mike Caballero; his siblings: Annie Caballero, Esther (Herbert) Maynard, Anita (Clayton) Wilcox, twin brother Braulic (Patrica) Caballero, and Earl Krone; and grandson Mackay Mathis, of whom he was so proud of.

Urnbearers are Mara Mathis and Jake and Josh Lilly.