James Michael Caldwell

Brigadier General (Ret.) James Michael “Mike” Caldwell, Oregon Army National Guard, was born in LaGrande, Oregon on July 27, 1951 to Donald and Barbara Caldwell. At St Joseph’s Hospital, an Irish nun took one look at him and said, “this baby is Mike, not James.” From then on, he was Mike. He is survived by his wife of nearly 50 years, Krissa, his daughters Erin Caldwell of Newberg, Oregon, and Kacie Caldwell of Boise, Idaho, his four grandchildren whom he adored and loved deeply, Siena, Nora, Theo, and Henry, and three brothers, Pete (Kathy) Caldwell of La Grande, Kevin (Connie) Caldwell of Salem, and Pat Caldwell of New Plymouth, Idaho. He was preceded in death by his infant son Kristopher in 1977, his father Donald Caldwell in 1986, his brother Robert (Bob) Caldwell in 2012, and his mother Barbara Caldwell in 2015. Mike filled his family’s world with stories, laughter, and the kind of scrappy, wholehearted creativity that made life feel bigger and brighter just by having him in the room. He was the dad who showed up for everything - every game, every performance, every moment that mattered - often still in uniform, coming straight from work. He did nothing halfway. Halloween meant full-sized candy bars and haunted houses in the basement. School projects became engineering feats. A simple toy became a treasure: the year he discovered Tetris, he bought out Radio Shack so he could surprise his nieces and nephews. He adored Christmas with childlike joy - piles of gifts beneath the biggest tree he could find on the lot, antique ornaments that reminded him of growing up, and the truly legendary Christmas parties at our Dorchester home. He expressed his love in unmistakable ways. He was a refuge for the kids and grandkids - the grandpa who filled his pockets with snacks “just in case,” who said yes to anything they wanted, including buying the stuffed animals their moms had already said no to or the bows that would later end up in his hair during a game of beauty salon. To his grandkids, he was safety, softness, and an unconditional yes. He spun wild Chester the White Mouse stories that soothed them through bedtime fears, heartbreaks, and the ordinary hard things of growing up. Chester wasn’t just a character; he was Mike’s way of saying, “You’re not alone. I’ll walk through this with you.” And he always did. Mike believed the world was meant to be met boldly, and his advice reflected that - from practical guidance to hilariously unfiltered one-liners. For all his big presence, he shifted the spotlight easily to the people he loved, endlessly proud of his wife, his daughters, and his grandchildren. He lifted them up, bragged about them and celebrated every accomplishment. He was a mentor to countless people: his 21 nieces and nephews, young soldiers seeking direction, colleagues who relied on his steadiness, friends who needed perspective, and even the checker at the grocery store who walked away a little wiser after a chat with him. Through every season of his life, Mike was unapologetically himself: funny, fierce, stubborn in all the best ways, generous in ways that changed people, and unforgettable in the stories he leaves behind. He was deeply rooted in his Irish heritage, reflected in his love of music and in the way he gathered people and told stories. He will be remembered especially by his grandchildren for his karaoke skills and his passion for football. Go Beavs!! His imprint is everywhere - in the laughter, the courage, the traditions, and the love he poured into his family. The same bold spirit that shaped his family life also defined his decades of service. Service was not a role he played - it was ingrained in who he was. Just as he showed up fully for his friends and family, he showed up fully for his state and country leaving a lasting legacy. In 1971, Brigadier General (Ret.) Caldwell enlisted in the Oregon Army National Guard (ORARNG) and quickly rose through the ranks. Brig. Gen. Caldwell attended Officer Candidate School (OCS) in 1975 and was commissioned as an Armor Officer in 1976. From 1976-2011, Brig. Gen. Caldwell served as an officer in the ORARNG, which is a fully equipped military reserve force with a dual state and federally mandated mission to protect our communities against natural or man-made disasters and answer the call to defend the nation during wartime as well. During his 40 years in the ORARNG, Brig. Gen. Caldwell was assigned to thirteen vital posts, including Squadron Intel Officer, Squadron Operations Officer, Battalion Commander, Policy & Liaison Officer, and Engineer Plans Officer, to name but a few. While serving in the military, Brig. Gen. Caldwell also held civic public office positions and state board seats for over 20 years. He was elected to a 4-year term on the La Grande City Council at age 27, elected to the Union County Court as County Commissioner, and was also a member of the Marion County Budget Committee. Brig Gen Caldwell was tapped by the Governor and Adjutant General of the ORARNG to help lead eight integral State Boards including the Facilities Environment Management Board, the Central Labor Management Council, the Governor’s Public Safety Taskforce, the Oregon Workforce Investment Board Youth Committee, and others. In retirement, he served on the Prevent Child Abuse Oregon Board. In 2006, Brig Gen Caldwell was appointed by the Governor as Commander of the Oregon State Defense Force (ORSDF). The ORSDF is the official state defense force of Oregon and serves as a state-level military and emergency services reserve force. In addition, the ORSDF assists, augments or replaces the National Guard as ordered by the Governor. During emergency or disaster incidents, the ORSDF assists with rapidly deployable emergency communications, coordination, and incident command system expertise and support compliant with Federal Emergency Management Agency (FEMA) rules. Throughout his illustrious military and public service career, Brig. Gen. Caldwell earned numerous Military Awards, including the Legion of Merit, the Meritorious Service Medal, and the Oregon Distinguished Service Medal. Brig. Gen. Caldwell earned a Bachelor of Science degree from Eastern Oregon University in Community Service, so fitting for his life’s work. On the civilian side, Brig. Gen. Caldwell began working for the Oregon Military Department as Public Affairs Officer in 1988. He was promoted steadily and retired as Deputy Director of the Oregon Military Department in 2013. Brig. Gen. Caldwell was in charge of all armory and training camp construction and maintenance for over a decade. During that period, he moved the Oregon Military Department facilities aggressively toward energy independence, including the acquisition of Christmas Valley Radar Site, with the long-term intention of creating a significant solar energy generating facility. The Department was recognized nationally for its innovative and energy-efficient designs. In the late 1990s, Brig. Gen. Caldwell worked tirelessly and with great hope with his friend Denny Maloney developing a nationally-renowned juvenile justice model, the Oregon Youth Challenge Program (OYCP), the first of its kind in the nation and a model he used to mentor leaders in other states so that they could replicate Oregon's successful program. OYCP is Oregon’s only accredited statewide alternative high school, an intervention program for teens who have dropped out of high school. Nearly 6,500 Oregon teens have earned their high school diploma, an equivalency, or credit recovery toward graduation at OYCP. In lieu of flowers, the family requests donations to the Oregon Youth Challenge Program at Central Oregon Youth Investment Foundation c/o Sarah Elmer, 601 NW Harmon Blvd Ste 2, Bend, Oregon 97703; Yamhill County Action Partnership (YCAP) online at: https://yamhillcap.org/donate-money; or The Oregon Service Member Relief Fund (OSMRF), PO Box 14350, Salem Oregon 97309. A Celebration of Life for BG (Ret) Mike Caldwell will be Saturday, December 13th at 1300 hours (1:00 p.m.) at the Amphitheater at Camp Withycombe, 15300 SE Minuteman Way, Clackamas, Oregon 97015

James Michael Caldwell

July 27, 1951 - November 27, 2025