Long-term care for our nation's severely wounded, ill, and injured Service Members and Veterans and their families presents formidable challenges. In addition to physical injuries, conditions such as Traumatic Brain Injury (TBI) and Post-Traumatic Stress Disorder (PTSD) require sustained, lifelong support. While federal systems provide acute and rehabilitative care, gaps often emerge in managing the chronic and social complexities of recovery. Semper Fi & America’s Fund (SFAF), a non-profit organization, has developed a unique model of life-long case management, disability related financial assistance and supportive services that provides a continuous, personal relationship to severely injured Service Members and Veterans. This study utilizes a large dataset of case manager notes to explore the effectiveness of this approach and propose its core principles as a potential model for federal health professionals in preparation for the inevitable need to support future conflicts. The primary aim of this study was to analyze 289,160 anonymized case manager notes from the SFAF case manager database to assess four key indicators of well-being, including anxiety, suicidal ideation, substance use, and legal issues. Utilizing a word finding search within the case management notes, a longitudinal analysis was performed on a retrospective cohort of 18,245 Service Members and Veterans injured in Operation Iraqi Freedom (OIF) and Operation Enduring Freedom (OEF) from 2003-2014. Our analysis revealed interesting trends in Service Member and Veteran well-being associated with date of injury and when they joined the fund. Additionally, we found a correlation between sustained engagement with the case management model and the frequency of well-being indicators. This is the first study that suggests that a proactive, relationship-centric, and lifelong case management model can improve long-term outcomes for severely wounded Service Members and Veterans. Future research opportunities could include cost-effectiveness of the SFAF approach, highlighting specific, actionable best practices and integration for the Department of Veterans Affairs, Department of War, and Public Health Service to enhance longitudinal care and reduce the societal burden of veteran injury.