top of page

Through the Eyes of a Legend: Steve O'Brien

by Daniel Rossi

Source: LinkedIn post

Christopher Columbus High School is an exemplary example for Catholic institutions around the nation. With an enrollment of 1,700 students and more than 14,750 alumni, the school is famous for bringing out brilliance in all of its students. Columbus has been known to influence several young men's future involvement with the school for the rest of their lives.

Mr. O'Brien, a lifelong history teacher known around campus as OB, is a prime example of a Columbus alum who stays true to his origins. In his 42nd year of teaching, O'Brien reflects on how Christopher Columbus High School affected his life from his early years to his 40-plus years as a teacher.

In 1972, O'Brien graduated from Columbus to begin his career as an Explorer. Looking back on some of his best memories from his time at Columbus, O'Brien emphasized how much his first-year history teacher, Mr. Burrus, influenced his love for history. Looking back, O'Brien says that his love of history inspired him to pursue a career in education.

"History allows us to simply hop into a time machine and roam,” O'Brien said.

Following his graduation from Columbus in 1972, O'Brien attended several universities, including Florida State University and Florida International University. Initially not intending to pursue a teaching career, O'Brien worked for the U.S. Department of Agriculture at the notorious Mutiny Hotel on South Bayshore Drive. Soon after pursuing careers unrelated to teaching, O'Brien discovered his passion as a teacher once more and, in 1981, O'Brien finally received his opportunity from Brother Edmund after several attempts to get employed.

An image recently shared by another CCHS legend, John Lynskey, on his Instagram page.

When he started teaching, O'Brien found new interests and became a coach. O'Brien, who he says had a limited athletic career growing up, discovered his passion for coaching cross country and track and field.

"Those who can't play, coach," he said.

O'Brien, who had spent his whole life running, had a strong social connection to the sport. Coach O'Brien earned Columbus its first cross-country state win over two decades later. By this time, O'Brien had firmly improved his reputation at Columbus. His relationships with his athletes stand out as the finest coaching memories.

O'Brien reflects on a particular relationship he had with a student, recent cross country coach, and current history teacher, Eric Pino, whom he had advised. With so much success, O'Brien was comfortable in his position and couldn't have asked for anything more.

"When I was coaching cross country, we felt more like a gang than an actual team," O'Brien said about the team's camaraderie.

After 20 years of coaching success, O'Brien chose to focus on teaching. O'Brien knows how life and teaching have evolved in the past 40 years and its state with the current generation.

Many things in Columbus have changed since his start. One aspect he points out is air-conditioned classrooms. He still hasn't mastered the technology aspect of education and has had a hard time adapting. But O'Brien being O'Brien, the legend that he is, he overcomes the challenge of technology by, "continuing to apply outdated methods to make instruction enjoyable and unique," he says.

In addition to his other well-known efforts, O'Brien founded the long-distance kayak team Castaways Against Cancer. Since 2000, the squad has helped the American Cancer Society fund more than $1.9 million for cancer research with over 3,680 miles paddled and 340 miles cycled. The Castaways continue to break Florida Keys Chapter fundraising records. O'Brien has shown his commitment to this well-known organization by paddling his way toward a cure for cancer during the organization's 20-plus-year history. O'Brien claims that spending seven days on the sea between Key Biscayne and Key West is the best thing that has ever happened to him.

Source: Castaways Against Cancer

The motivation to start the Castaways came from the death of O'Brien's mother from lung cancer in 1999. It inspired him to start a remarkable organization to work toward finding a cure. O'Brien's physical condition became a problem, despite his healthy mental state. He suffered a serious cardiac episode in 2005. From there, O'Brien changed several aspects of his lifestyle, such as his food and level of stress management, and he dedicated himself to becoming a yoga instructor and an enthusiastic student of Tibetan Ayurveda.

"I tell everyone I meet about our mission and my personal ministry, trying to become more educated in the direction of new cures, and actively volunteer my services to anyone who could use a little love," he said about the Castaways mission on their website.

O'Brien continues to succeed in life by focusing on his priorities, which include teaching and paddling. O'Brien may not view himself as a hero, but he offers this advice to others seeking success regardless of their position, saying, "If you set your mind to something and give it your all, you won't give up and if you don't come back, you'll give up, and you know where it gets you."

Returning to the present, while educators have learned many techniques throughout their careers, O'Brien's initial method was straightforward.

"I believe the lesson I've taken away from this experience as an older man is to never undervalue the gift of trust. It would be wonderful if you had the gift of faith. Keep it together. I know that now," he said.

O'Brien says he'll never retire but, if he could go back he would change one thing.

"If I could go back to being a young man again - just try to be one percent better than you were yesterday," he said. "You get up in the morning, say one more prayer, or do one more act of kindness. Just try to be one percent better than yesterday. Be a better version of yourself every day. Just a little bit. And I think you'll be what Columbus wants you to be."

O'Brien took a lot from this school after spending so much time in Columbus. There is just one Christopher Columbus High School in his opinion. And no matter how hard you try, you can't explain it to anyone.

"There is something wonderful going on here that is simply impossible to express. Yes, there are problems. Everyone has problems. But there is something about Christopher Columbus High School that makes it such a nice place to be, no matter what happens at the end of the day."

After 40 years in Columbus, O'Brien can only see the positive aspects of our community. He remained devoted to Columbus because the school became a part of him with the Columbus Brotherhood, and he would never regret his origins. O'Brien will continue to be one of Christopher Columbus' greatest figures for years to come, serving as an example for others to follow in his footsteps in terms of success and gratitude to Christopher Columbus High School.

Mr. O'Brien. OB. A Columbus ORIGINAL. A Columbus LEGEND.

153 views0 comments

Recent Posts

See All

Seniors Last Will & Testament - Class of 2024

In alphabetical order below: I, Richard Aguilar, being of sound mind and body do hereby bequeath: Mr. Ciocca take you for Mr. Darp I, Lucas Alonso, being of sound mind and body do hereby bequeath: to


bottom of page