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CSM Scott Bailey

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The Man Behind Our Mission

    Scott Bailey’s story is one of resilience, service, and the kind of leadership that truly puts others first. He was a high school dropout who did not join the Army until the age of 25, searching for something he could be proud of. He found exactly that. He enlisted in February 1989 and went on to serve nearly 30 years on active duty. He tragically passed away in 2017, just three months shy of his set retirement.

     His journey from high school dropout to achieving the Army’s highest enlisted rank, Command Sergeant Major, is a true testament to the man he was. Along the way, he earned a bachelor’s degree in business, never allowing his past to define his future. He achieved many great things, but the thing he was most proud of was being a dad to his three beautiful daughters. He was a fearless leader who loved his soldiers deeply and cared for them like they were his own.

     During a deployment to Iraq, that care became very personal. After returning stateside, our founder, Skyler, was diagnosed with pulmonary tuberculosis. Scott made sure she received the medical care she needed and even adjusted her work so she could continue serving. When she was eventually medically discharged due to complications, he did not walk away. He stood by her through one of the darkest seasons of her life, when she was battling depression and suicidal thoughts, and helped her find purpose again.

     Scott’s impact reached far beyond one person. He never judged his soldiers by rank, race, or religion, only by their heart. He showed up for them time and time again, often in quiet acts of kindness that meant everything. Even after his passing, his soldiers have traveled from across the country to visit him at Arlington, which speaks volumes about the kind of leader and man he was.

     He loved dogs, especially Great Pyrenees, and would often bring his dog Scotch Brite to work to lift morale for his troops. He often talked about starting a dog rescue on his land after retirement. You could truly see his heart and his love for animals in the way he cared for them.​

     In 2014, while serving as a brigade Command Sergeant Major at Fort Hood, he shared what mattered most to him:

 

“What we do not do is compromise when it comes to taking care of our soldiers. We make sure their medical, behavioral health, financial, and administrative needs are handled before they deploy. There is nothing more important than making sure they are ready to return home and reintegrate with their families. That is our number one priority.”

©2026 by Bailey Military Support

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