Distinguished Alumnus

St. John's Prep is proud to announce David Hennessey '83 P'16 as the School's 2024-2025 Distinguished Alumnus

Each year, St. John's Prep proudly recognizes an alumnus whose life personifies the spirit and values of the Xaverian Brothers and the extraordinary commitment of our faculty and staff. In all endeavors, this individual models for fellow alumni what it means to be a Prep graduate and inspires current students to be change makers and forces for good in the world.

Dave Hennessey is someone anyone would want to meet. It’s not just how he sees the world that draws you in, it’s how he navigates it. His worldview, seen through steadfast eyes, is one where the ordinary can always become the extraordinary. A belief system where dreams are still out there and still come true.

For those reasons and many others that Hennessey, a longtime finance professional and a social studies teacher at the Prep since 2008, is the School’s 2025 Distinguished Alumnus. The award honors a St. John’s graduate whose life exemplifies the spirit and values of the Xaverian Brothers and inspires current students to be change-makers and forces for good in the world. 

Hennessey family connections at St. John’s run deep. His late father, Paul ’52 P’83 GP’16, was renowned for his lifelong devotion to the School community and was named the Prep’s Distinguished Alumnus in 1994. Two uncles and three cousins are also Eagles and so is his son, Dan ’16. At his own graduation, Hennessey won the Mr. St. John’s Award (now known as the Xaverian Award). 

He earned his degree in economics at Dartmouth, then worked in institutional equity trading for 20 years across three firms. Wall Street can be an unforgiving construct. One person’s fortune can be another’s misfortune. A study in contrast, it’s the world’s financial center, packed into 0.453 square miles that feature a significant homeless population. 

Hennessey had no illusions while toiling in New York and, later, Boston. He understood market economies, he understood clients, and he was good at it. But in the final analysis, it was leaving Hennessey unfulfilled.

"There were circumstances about Wall Street that challenged me,” he says. “That can happen in any business, but after 20-plus years, I felt a call to serve in a way that more directly impacted folks, especially young people.”

Hennessey’s vision was bigger than bulls and bears and bundled real estate. And yet, the truth about who he is has less to do with the realities that nudged him back to the Prep than it does this: Dave Hennessey has always been a perfect fit here.

"From my perspective, he’s a living role model for what we want our kids to be,” says religious studies teacher Steve Ruemenapp. “He’s so ethical. He’s thoughtful, he’s kind. He gives a lot of his time, but he doesn’t take himself too seriously. He shows up for people. I think he’s deserving of this award because he’s really living out what it is to what we aspire to here.”

“From my perspective, David is a living role model for what we want our kids to be. He’s so ethical. He’s thoughtful, he’s kind. He gives a lot of his time, but he doesn’t take himself too seriously. He shows up for people. I think he’s deserving of this award because he’s really living out what it is to what we aspire to here.”Steve ruemenapp, religious studies teacher

GOOD INCARNATE

Part of how Hennessey carries himself—with a humility, credibility, and respect that makes people stand taller when they’re around him—originates from a person he never met. The man was Brother Linus, C.F.X., a St. John’s religious studies teacher, counselor, and coach until his death in 1977, two years before Hennessey came to campus. It wasn’t just how often the Brother was mentioned, as Hennessey remembers it, but more so the context. Favorite coach. Favorite teacher. An easy familiarity. A guy kids sought out just to hang out. 

"The theme of the stories never wavered and he was always the one guy I wished I’d met,” Hennessey continues. “I don’t think I ever consciously thought, ‘That’s how I’d like to be remembered.’ But I do think I realized, ‘If I’m doing this life thing right, that’s what it should look like.’”

The 20th Century cracker barrel sage Will Rogers once said, “Live your life in such a way that you wouldn’t be ashamed to sell the family parrot to the town gossip.” That’s Dave Hennessey.

"He exemplifies the Xaverian values to the highest degree,” says Jake Vana ’24, now a Princeton freshman. “If you were struggling and needed someone to talk to, everyone would go to him. He’s the perfect combination of serious business, fun times filled with laughter, and times of compassion for all those he encounters. He’s truly one of the best people you could ever meet and St. John’s is a better place because of him.”

DEEP IMPACT

Being accepted, embraced, and even well-liked doesn’t mean you can teach. Though Hennessey joined former faculty member Anne Gamer P'08 in teaching economics, and their collaboration led to increasing student interest and expanding enrollment in the economics classes, he admits there was a learning curve, and early on, he leaned heavily on his wife Jackie, for encouragement and reassurance that his career switch was not ill-advised. 

"This is just an easy place to bump into a lot of different people. We continue to work toward a more diverse campus, but we have a strong diversity of skills and interests at St. John’s. You don’t have to go far to find somebody you can learn from.”

According to Curt Dalton ’92 P’26 ’27 ’29, Hennessey’s people skills, boundless humility, and pure heart ultimately made him a natural. 

"If there were a Hall of Fame of inspirational people you’ll be talking about for the rest of your life, he’s in it,” says Dalton, who has co-taught the Prep’s Ryan Shaw ’15 Entrepreneurial Education Program with Hennessey for the last 11 years. “There are thousands of men out there who’d say he’s a major part of how they succeeded.” 

Hennessey, meanwhile, isn’t sure being known as Mr. Nice Guy qualifies him to join the Prep’s four-decade legacy of distinguished alumni. But in his own, gentle way, he’s grateful."I teach class a few times a day and do my best to be there for folks, but it’s not like I’m out solving the world’s problems anywhere, so yes, this caught me by surprise. I hope that the common thread between me and those other honorees is loyalty to the mission. For me, at the end of the day, it’s still about the Brothers’ vision.”

Established in 1995, the Distinguished Alumnus Award allows the St. John's Prep community to present a living example of faith, brotherhood, and wisdom to our students. We continually strive for excellence in all we do, and our Distinguished Alumnus is someone who has achieved professional success, has shown a commitment to lifelong learning, pursues enduring personal relationships, and serves as a model for servant leadership in the Catholic and Xaverian tradition.