In June 1993, a nervous Tito Jackson addressed his senior class upon the graduation stage about all of their bright futures ahead of them. 21 years later, with more confidence, a more experienced Tito Jackson took the stage once again, addressing the 2014 graduating senior class, stressing that they must “decide whether you’re going to make a difference.” He learned this piece of advice in his four years at the high school and had applied it to his own life.

Boston City Councillor Tito Jackson’s experiences at the high school, including involvement in racial equality clubs and the encouragement of his teachers, have shaped him and his political career.

Tito Jackson grew up in Roxbury and went to school in Brookline. He is dedicated to solving local issues such as the achievement gap, housing inequality and crime.

According to Jackson, he most vividly remembers general feelings about the high school rather than specific memories.

“I remember an environment that was willing to have difficult conversations about race, about gender, about class, about religion,” Jackson said. “I remember having a lot of fun. I warmly remember being stretched in many ways around my thoughts, opinions and preconceptions. It was a really rich experience for me.”

Jackson said that memories from an African-American history class he took in his sophomore year stay with him the most.

“It was a real turning point in my life because prior to that, I didn’t have an understanding of who I was in the context of history,” Jackson said. “In fact, it actually synced with what I studied in college. I concentrated in African-American and women’s history.”

According to Jackson, his teachers at the high school pushed him to his fullest, ignoring all his doubts of himself.

“I had a lot of people who spoke encouragement into me, even when I was not performing anywhere near my potential. I count that as a very pivotal component in who I am today,” Jackson said. “I don’t believe that I’m extraordinary, I believe that I’ve been given extraordinary opportunities.”

English teacher Laura Sheffield taught Jackson in his sophomore year in a class called Multicultural Literature. She remembers his exceptional abilities to connect with others in and outside of class.

“He was really friendly and really calm,” Sheffield said. “I just remember him as being an outstandingly easy-to-get-along-with-kind-of-guy, and he seemed to get along with other people in the class. I felt at the time that his social skills were above and beyond, even as a sophomore.”

According to English Curriculum Coordinator Mary Burchenal, who taught Jackson in his senior year in a class called Senior Seminar in Public Policy: the AIDS Crisis, Jackson was a very lively people-person.

“Everybody knew Tito,” Burchenal said. “He just was a friendly, outgoing, magnetic personality who always brought his sense of humor to the class. He was always a really active participant, always at the center of discussions.”

Beginning with his time at the high school, Jackson wanted to make changes in the way students viewed racial equality.

“I was in the Student Alliance Against Racism,” Jackson said. “We had a really forward thinking headmaster, a young guy at the time. We had Black kids, we had White kids, we had Jewish kids, we had Christian kids, we had Muslim kids. It was all of us together. We had some really important seminal conversations at that time for our school.”

According to Sheffield, though the atmosphere at the high school during Jackson’s time was accepting, there were many issues that needed to be solved.

“I think that {BHS} is never an easy school for people who are outside the upper-middle class region. Whatever their ethnic backgrounds are, it’s always been tough,” Sheffield said. “Tito was an engine for change when he was here. He was determined to make it work for him, and he did.”

Jackson said he values his experiences at the high school because he learned to appreciate all types of people and backgrounds. He also considers the time spent at school to be transformative because of how his perspectives were challenged and reimagined.

“It really shaped a very practical ability to connect cross-culturally, to stretch my own understanding of culture and history and religion and sexuality and just structural and institutional rightism,” Jackson said.

Looking back and appreciating his education at the high school, Jackson said he has made it a priority to close the achievement gap in the Boston and greater Boston school systems.

“There’s still huge inequality in what is being offered in Boston at some schools versus what is being offered at other schools, just in Boston,” Jackson said. “I know it what it feels like to be in a great school system, and I believe that every student in Boston and Massachusetts should have the same caliber of education that I received at Brookline High School.”

Burchenal said that Jackson clearly shows in his policies how much he is appreciative of the education he received from the high school.

“He cares so passionately about education. He conveys in everything he does now how important this education is,” Burchenal said. “I think that he is very grateful for the education that he got at this high school. He has a big future in Boston politics.”

Despite losing the recent mayoral election to Boston Mayor Marty Walsh, Sheffield said that many people still support Jackson in his municipal endeavors.

“I think he has a career ahead of him, and I think this past mayoral race was incredibly exhausting,” Sheffield said. “So many people were behind him. I have to say, I really hope he gets into more and more leadership positions, because I think he has got a lot to offer.”

Jackson encouraged BHS students to take advantage of their time at the high school and its opportunities. 

“If I were speaking to the skinny Tito from high school, I just would say absolutely make the most of it, get it all,” Jackson said. “Understand that you have a really amazing opportunity, and it’s up to each of us to seize the day and to ensure that we get all of the potential and experience that we can out of that great school.”