WASHINGTON — On a summer morning in 2022, Kaileen Santos met with her supervisors in a Pentagon office. The staff sergeant considered leaving the Army to pursue a career in law enforcement or work for the government.
Maj. Josefina Martinez and Lt. Col. Izabella Lundy saw her as a Soldier who could innovate and thrive in challenging environments, and they didn’t want to let her go, so they encouraged her to apply for the Army’s Green to Gold Program, an initiative that provides enlisted Soldiers a means to earn a college degree and an officer’s commission while remaining in the Army.
“I [saw] the strength and motivation to do more for herself and her daughter,” Martinez said.
Santos applied for the scholarship with Martinez and Lundy’s encouragement and was accepted into the Green to Gold Program in December 2022.
Santos, the first member of her family to join the armed forces, will study health systems management at the University of North Carolina at Charlotte this fall. She will continue to receive her current pay, a stipend, basic allowance for housing and basic allowance for subsistence, which will help pay for tuition, textbooks and rent. Her Post-9/11 G.I. Bill benefits she is saving for her daughter’s education.
Santos will attend ROTC during the school year and a cadet summer camp between her junior and senior year.
“I never thought I'd get this chance or opportunity,” she said. “The changes that it’s going to make in my life — in my daughter’s life — it’s such a great feeling.”
Hometown hard knocks
Santos’ soft-spoken demeanor masks a tough interior from growing up in a rough neighborhood in southern Massachusetts.
New Bedford, a small coastal city settled on the Acushnet River along Massachusetts’ south coast, attracts tourists for its architecture and colonial history. But its gothic and federal-style buildings and the charming ambiance of its downtown hide a dark turmoil in its lower-income neighborhoods.
The town grew into a hotbed for gang activity, with 11 known street gangs, including the Latin Kings. In 2021 the city reported that 20% of its residents lived below the poverty line, with more than 80% classified as economically disadvantaged.
Youth in New Bedford often become addicted to narcotics, and some turn to prostitution.
“You walk down the street, and you see girls getting sold,” she said.
Santos’ mother Maria, a Honduran immigrant from San Pedro Sula, settled in New Bedford in the early 2000s. Santos lived with six siblings in the family’s modest house on the city’s west side. Her mother ran a Spanish grocery store which she has owned for 20 years.
Some of her classmates fell into a life of crime or joined a gang. One of her peers became pregnant at 12 years old. Santos saw several of her friends fall into the web of substance abuse, and many were absent from school. A male friend who fell into depression later committed suicide.
Santos admitted she didn’t focus on academics as a teen.
“I didn't really see a purpose in school when I was 18,” she said. “I was … naive and immature.”
Fortunately, Santos met retired Lt. Col. Kevin McGovern, an advisor at her school’s JROTC program. McGovern acted as a mentor not only to Santos but to her siblings. He saw potential in Santos and encouraged her to enlist in the Army and leave New Bedford.
“He tried to keep me on the straight and narrow,” Santos said. “He always kept an eye on me [and] encouraged me to do better.”
After graduating from New Bedford High School in 2012, Santos saw the Army as a path out of her hometown.
Santos enlisted and received a job as a human resources specialist, and the Army assigned her to Conn Barracks in Schweinfurt, Germany. She found Schweinfurt to be a beautiful, vibrant city and a stark change from her life in New Bedford.
“It really opened my mind and showed me that there’s more to life out there,” she said.
An assignment at Fort Knox, Kentucky, followed her tour in Germany, where Santos met and married her daughter’s father. At Fort Knox, she weathered the most tumultuous period of her life from 2015 to 2016, when she went through a divorce and became a single mother.
Santos eventually adapted to raising her daughter alone while thriving as a Soldier. She had successful stints at Fort Meade, Maryland, as a drill instructor, and then in her current position at Army headquarters.
Santos took college courses sporadically in her first years in the Army, but at Fort Meade, 1st Sgt. James McKay encouraged her to dedicate herself fully to her studies. She later began exploring leadership opportunities, including warrant officer options and commissioning opportunities.
Becoming a mother also changed her, and she became fiercely protective of her daughter, a seven-year-old who loves swimming, karate and gymnastics. Santos even became PTA president at her daughter’s school.
She also excelled in her duties as a Soldier. At Fort Meade, her commander selected her to compete in the 53rd Signal Battalion’s Best Warrior Competition in October 2018.
For the competition Santos ran kettle bell runs, performed simulated first aid and competed against five male counterparts in wooded areas north of Baltimore.
Santos was selected by the Department of the Army for special duty as a drill sergeant at Fort Jackson, South Carolina, before her assignment at the Pentagon.
“The Army’s definitely helped me find direction in life,” Santos said. “It’s always given me a goal to work towards.”
Under her wing
In her first 11 years in the Army, Martinez made a name for herself as an energetic NCO, climbing through the enlisted ranks quickly.
Martinez and Santos’ careers converged in Washington in 2021, when Martinez was the assistant executive officer for Director of Army Staff Lt. Gen. Walter Piatt, and Santos served as the executive assistant and human resources NCO.
Martinez saw a bit of herself in Santos during their time at the Pentagon. Like Santos, Martinez left home at 18 and eventually landed a position as a senator’s office manager on Capitol Hill. But later, Martinez divorced her husband and had to adopt to life as a single mother.
Martinez enlisted in the Army in 1995, eventually finding her niche as a career counselor. Then she reached a crossroads in her career. Martinez found she adapted well to the Army structure and lifestyle, but decided she could better serve the Army, and care for her family, as an officer. She commissioned in 2006.
Now in her 50s, Martinez took the younger Santos under her wing, teaching her the importance of working collectively in the Office of the Director of Army Staff.
Santos learned quickly. Working in the same building as the Army’s top general officers didn’t faze her, and she became a trusted assistant of Piatt. Santos never let her career aspirations interfere with her role at Army headquarters, often redoubling her efforts after taking time off.
“She just instinctively knew what she was doing,” Martinez said. “She was always polite; she was just ahead of the game.”
Santos saw how the bonds she formed with her mentors — officers and senior NCOs — influenced her career and her life. She remembered how Capt. Jason Selby, company commander, Headquarters and Headquarters Company, 19th Engineer Battalion, shielded her from unnecessary hardships at Fort Knox.
And she recalled the efforts of Martinez and Lundy to encourage her to apply for the Green to Gold Program. She wants to do the same for another Soldier and hopes to one day become a company commander.
“Staff. Sgt. Santos is a dedicated Soldier who is talented and committed to service in the Army,” Piatt said. “She is example of selfless service, and it has been a pleasure having her serve on my team.”
“[Santos’] accomplishments and potential to lead our Soldiers has risen to the level that is characteristic of a commissioned officer,” said Deputy Undersecretary of the Army Mario Diaz, a former Army officer and West Point graduate. “I am confident she will continue to be successful.”