In an episode of ‘The Bounce Back podcast with host B Luke, Cilo, a resident of Lynn, Massachusetts, shared his transformative journey from a decade behind bars to a new life shaped by education and personal growth. Released in June after serving nine years of a 10-14 year sentence, Cilo’s story reveals the challenges and redemption he has faced.
Cilo’s early years were shaped by adversity. Born to a 17-year-old mother, he spent his childhood in the Dominican Republic before moving to the United States at age six or seven. With no English skills upon his return, he had to relearn everything from scratch. Though described as a bright student, he often found himself torn between academia and street life. His boxing years from 14 to 18 briefly instilled discipline and focus but ultimately couldn’t shield him from legal troubles.
Cilo’s encounters with the law began in his youth. He committed juvenile offenses, such as breaking into cars and trespassing, with his first institutional experience being in the Department of Youth Services after a school altercation. His path escalated when, at 16, he was arrested in Alaska with a kilogram of cocaine. Frequent stints in county jail, including Middleton, punctuated his young adult years. However, a turning point came in 2015 when Cilo was charged with manslaughter for selling fentanyl that led to an overdose—the first such case in Massachusetts.
During his time at facilities like Walpole, Shirley Medium, Maximum Security, and Concord, Cilo underwent a profound transformation. Solitary confinement served as a wake-up call when he read a book detailing success stories from other inmates. This inspired him to replace “hood books” with self-help and entrepreneurial reads. Engaging in prison education programs, he found purpose in pursuing a college degree, noting that education gave him hope, structure, and a supportive community.
Today, Cilo is working toward a bachelor’s degree, viewing education as a “blessing in disguise” that may have saved his life.
Earning an associate’s degree while incarcerated, Cilo graduated alongside 14 of his 17 cohort members. He now participates in the “My Turn” program, offering formerly incarcerated individuals a 14-credit pathway over 10 months to further their education. But reintegration has not been without hurdles—finding employment remains challenging due to his record. Despite setbacks, Cilo stresses resilience, stating, “There’s going to be 400 NOs, you just need one YES.”
Cilo speaks openly about the challenges of prison life, including the constant need for vigilance and inadequate mental health care. Yet, he found a sense of purpose by tutoring Spanish-speaking inmates and hopes to guide youth away from the path he once walked. Post-release, he seeks positive outlets like kayaking and family time, while documenting his journey through his “Back Outside” presence on TikTok.
His future ambitions include building a stable family, inspiring youth through speaking engagements, and exploring music production. Cilo’s main message is clear: success may look different for everyone, but achieving it demands commitment, resilience, and a willingness to change.
