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Rooney Real Estate
Commonwealth Cooperative Bank
August 22, 2013
Anthony O'Leary's Journey
By Kevin Devlin

As a young boy, Anthony had a tough life. Admittedly, he was lost and felt abandoned.    

“Growing up, my family was fractured,” he said. “My mom and dad separated before I was born. I lived with my grandmother, great-grandmother and uncle. My grandmother was raising me because of my mom’s struggles with addiction and mental health issues. My father started a new family and had very little time for me. The occasional Burger King drive-through and video game drop-off was the extent of his involvement. I was without my mom and dad and felt I was left to face life on my own. My great-grandmother was in her late 80’s and my grandmother was older as well and worked full time and was too exhausted to play or spend time with me. In the fourth grade I was diagnosed with ADD and have been taking medication ever since then. My lack of family support and friendships left me feeling so alone. My only outlets were the TV and video games. It was the only time I expressed emotion. But then a glimmer of hope, my mom had completed a lengthy recovery program and I began visiting regularly.” 

There’s a saying that tough times don’t last but tough people do, and Anthony is a tough kid who’s on the right path in life. His reunion with his beloved mom and transitioning into a new family was instrumental in steering him back on course.

“Learning to trust and love my mother was a gradual process,” he said. “I had to deal with all types of feelings. As my mom got healthy, the visits increased. Not only was I re-united with my mom, I was now seeing my step-dad and their children. But sometimes I felt as though I was still alone. I was afraid to be abandoned again. Gradually, they began to express how they wanted me to stay full-time, and that was around the time I asked my step-dad if I could call him Dad. We decided we’d get an apartment and move in together. 

“Now…I had even more pressure to be a good student because I knew the good grades would bring my mom happiness,” Anthony added. “I believe this is where my drive came from, and with the encouragement from my family through daily reminders; I was able to see my strengths and my weaknesses. I was reminded if I needed help to ask and I would receive it; and that I was accountable to my family. I needed to be responsible for my actions. This discipline, love, and support gave me a positive approach to daily life. For the first time I started putting an honest effort into everything I did and openly admitted when I was wrong. Through positive affirmation and a lot of trial and error, I was reminded more times than not that my parents had my best interest at heart. In the seventh grade, I had sixty-two detentions and was thrown off my sport’s teams; in the eighth grade, I only had twelve detentions and was asked to speak at my eighth-grade celebration. During that speech, I expressed my desire to become a better student, teammate, and person.” 

Along with reuniting with his family, two other factors played a crucial role in his awakening. He found God again and goes to church every Sunday. And, he started working out at Peter Welch’s gym (owned by his uncle) which changed him both physically and mentally in a positive fashion. 

With his newfound confidence he embraced the high school experience at the Boston Collegiate Charter School. Focusing on life he started liking the person he was becoming and enjoying the positive attention he was receiving. He was elected into Student Government. In his freshman and sophomore years he was a grade representative. As a junior he was the treasurer in charge of fundraising and senior year was elected president. Anthony was inducted into the National Honor Society. He was accepted into the coveted Minds Matter and Summer Search program. He was a Leave No Trace program trainer. He won the school’s math award as a freshman and sophomore. 

In sports, Anthony’s experience in the local sports’ programs-Pop Warner, Gatey CYO hoop, and youth baseball-prepared him for success on the high school level. He was caption on the varsity hoop team for four years. He was on the varsity baseball team and team captain as a junior and senior. The baseball team won three consecutive state charter school championships. 

Embracing his metamorphosis, Anthony became adventurous. He wasn’t going to waste his summers. In July, 2011, he attended the Taft Summer School in Connecticut and studied enhanced skills in mathematics and biology and acted in a play. In August, 2011, he attended the National Outdoor Leadership School in Wyoming. In late June, 2012, at Stonehill College, he participated in the Boys State program which focused on government, economics, and leadership. 

In early July, 2012, he attended the Summer Leadership Institute held at Brown University and studied social entrepreneurship, positive impacts of non-profit organizations, and enhanced leadership skills. In late July through mid-August, 2012, he participated in the Deer Hill Expeditions in Costa Rica. He volunteered for community service, painted school facilities for the indigenous people, and planted trees in a previously-flooded area hoping to prevent further erosion. This summer, he’s city council candidate Marty Keogh’s South Boston campaign manager. 

Anthony feels these programs made him a better person rescuing him from negative peer pressure in Southie. He felt happy to be “above the influence” but most importantly, “a son to my Mom and Dad, and a big brother to my brother and sister.” His motto is “The Journey is the Reward.” 

He graduated last June with a 3.60 GPA. He was a recipient of the Christian A. Herter Memorial Scholarship, a full academic-scholarship, and will attend Holy Cross in the fall.

I officiated some of Anthony’s games when he played for Gatey. He had an edge about him, seemingly unhappy and a bit troubled. I guess rambunctious might best describe him back then. 

Listening to his story I was emotionally-enriched. It was wonderful. Craving eye-opening experiences he feels good about giving back and being open-minded. He’s happy striving to be true to himself and desirous of realizing his full potential. 

I’m proud of him. He’s become a polite, mature young man. 

I told him, “Tough times don’t last, but tough people do.”

He smiled. He liked that phrase and I think he’ll store it near his heart as he journeys through life.   



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