The Spire

James Condon ’30

Staff Writer

MINEOLA, N.Y. – Late last month, a high school athletic center was transformed into a gala space as three Holy Cross alumni were celebrated for their personal and professional leadership.

The Legacy of Leadership event, organized and hosted by Chaminade High School, honored three of its graduates who went on to become distinguished Holy Cross alumni: former NBC CEO and founder of Autism Speaks Robert Wright ‘65, Fidelity Brokerage President Thomas Jessop ‘88, and Associate Head Coach of the Chaminade High School Crew Team John Callinan ‘88. Mr. Wright and Mr. Callinan were awarded the school’s Founders Award, while Mr. Jessop received its Distinguished Alumnus Award.

Throughout the program, the theme of a united set of principles guiding individuals pursuing unique professional fields was harped on again and again. This was echoed both in the keynote speech given by Chaminade’s President, Brother Thomas Cleary, and in a letter written by President Rougeau.

For Mr. Jessop, it meant helping to create the infrastructure that allows institutional investors to safely buy, hold, and sell crypto assets through launching Fidelity Digital Assets in 2019. In his role as President of Fidelity Digital Assets, Jessop utilized both new and traditional safeguards, such as cold storage and institutional custody, to create the infrastructure demanded by firms to take Digital Assets seriously in the financial market. After the success of Fidelity Digital Assets, Mr. Jessop assumed the role of President of Fidelity Brokerage.

Beyond his institutional success, Mr. Jessop was praised for his role as a father, as well as his humility and character.

When asked by The Spire how Holy Cross shaped his personal and professional life, Mr. Jessop stressed the timeless value of a liberal arts education.

“We need to create young people who know how to learn, to think on their feet, to be critical thinkers and do the things that machines can’t do. I think there is a Renaissance in liberal arts, and I believe very strongly in Holy Cross’ mission, which is very similar to Chaminade’s, which is developing people for others.”

As for advice to Holy Cross seniors heading off the hill, Mr. Jessop kept it simple: “The early parts of your career should be focused on learning and observing.”

“Your entire career is not going to be defined by what you do in the first couple of years, and the key thing is to learn some skills, apply them to the next job, learn some more skills, and become a well-rounded corporate athlete or whatever you decide to do … become someone who can think differently, who can add value”

The key to doing that, Jessop says, is “Trying different things as a young person. So don’t be afraid to take some risks if you’re passionate about learning a new subject.”

Jessop’s classmate John Callinan was next to be honored. Mr. Callianan played a significant role in the creation and development of Chaminade High School’s crew program, which ballooned from a group of forty kids to a dominant hundred-man-strong national powerhouse, recently placing 4th in the 1500m at the 2026 SRAA Nationals.

Callinan reflected on how Holy Cross introduced him to rowing. “(I) went up there to play baseball. I didn’t want to sit on the bench. So my RA at the time said, ‘Listen, why don’t you try rowing?’ Fell in love with it.” When Callinan returned to Chaminade to teach, “I knew I wanted to start it here at Chaminade, and within a number of years I got it started.” The influence of Holy Cross has bled into his personal life, as teammates became “friends for the rest of our lives.” In addition to receiving the Founders Award, Callian became the namesake for the school’s crew fund and endowment.

The program was concluded by recognizing Mr. Wright, a man who transformed NBC from a national broadcast network to the most powerful cable television company in America. Following the presentation of the awards, Mr. Wright briefly spoke about his time as president of Cox Communications Cable, traveling town to town securing foundational cable franchising rights.

Yet, Mr. Wright’s leadership has extended far beyond the boardroom. Following the news of their grandson’s autism diagnosis, Bob and his late wife Suzanne founded the nonprofit Autism Speaks. The organization has made monumental gains in education, advocacy, and funding for autism research, notably spearheading the group behind the 2014 Autism CARES Act, which funded research in the amount of 1.3 billion over 5 years. Mr. Wright’s impact at Chaminade had previously been honored by the school through his role as the namesake of their speech and debate team, which he competed on the national level as a student.

William Clemens, an English teacher and the head coach of the high school’s debate team, described Mr. Wright’s legacy as “excellent.”

“There are so many guys here that were touched by his movement, with autism speaks, with his work, and also current speech and debate team members on our team, who literally have Robert Wright’s witness, legacy, example, as inspiration for their work currently in speech and debate.”

Ultimately, Mr. Jessop’s, Mr. Callinan’s, and Mr. Wright’s achievements were celebrated through the lens of how institutions had shaped them and how, in turn, they shaped institutions themselves.

This belief was echoed in a letter by President Rougeau, who wrote how the missions of Chaminade and Holy Cross “Though different in their founding, … share the same purpose. Each believes that education of the heart is inseparable from education of the mind, and that a life well lived is measured by what we give.”

This sentiment was seconded in an excerpt of an exclusive statement given by Chaminade’s President, Brother Thomas Cleary, to the Spire.

“Chaminade and Holy Cross share a commitment that education is about forming people of faith who put their gifts at the service of others. The Marianist call to be a family in mission and the Jesuit call to be men and women for others speak the same language.

For nearly 100 years, Chaminade graduates have found a home on Mount St. James. Tom, John, and Bob honor both of their alma maters with lives of leadership defined not by titles, but by the people they have lifted along the way.”

Overall, the event highlighted how the distinct paths of three accomplished Holy Cross alumni all converged on the starting principles of the high school and college that shaped them as they came of age. Through corporate innovation, athletic development, and advocacy for those vulnerable in our communities, the night showed how these three alumni practically applied the mission and principles of Holy Cross to life, wherever life had taken them.