Errol Saunders and the Legacy of Imagination

“Thank you for letting me speak to you from the heart. Notice there are, in fact, no notes,” said Errol Saunders II, after delivering a rousing and deeply personal speech that left few in the packed Academic and Performing Arts Center (APAC) with dry eyes. Saunders was on stage to receive the Hopkins Medal—the highest recognition the School can bestow—for the transformative two-decade impact he has left on Hopkins and its surrounding community. On that May afternoon, Saunders took the opportunity to give something back in return: a message of hope, possibility, and imagination.

Saunders’ own story—from a challenging Los Angeles upbringing shaped by persistence and community support, to a Yale education, to his 20-year tenure at Hopkins—is an illustration of the potential of education to change lives. Because his life and career have exemplified the message he delivered that day, no script was needed; he was simply sharing his truth.

Imagination Unlocked

Saunders’ speech began with a personal story of perseverance. Raised in Los Angeles, he recalled his family living on financial and housing assistance. Despite these economic constraints, Saunders said there were adults in his life who provided constant encouragement. 

His mother, for example, was a rock at all times.

“There was no shame associated with our poverty,” Saunders reflected. “This is just the way it was and we were going to do our best with it.” As a child, Saunders observed the power of community firsthand, as his mother, Roxanne Saunders, often welcomed his friends into their home after school, where everyone was expected to do their homework together. 

“Many of the kids I went to elementary school with did not go to college. Many of the folks I went to high school with did not go to college. Many of the people I spent a lot of my childhood with had a limited imagination of what they could be,” he shared.

A pivotal moment in high school helped unlock his imagination, changing the trajectory of Saunders’ life. As college applications loomed, his guidance counselor, Lynn Brody, insisted he apply to Yale—a school he hadn’t even considered attending. 

“She made me imagine it,” Saunders said. Later, as a semi-finalist for the Ron Brown Scholarship—a national program that awards four-year college scholarships to high-achieving, community-minded African American students—he was again encouraged by a mentor (this time Vanessa M. Evans-Grevious, now Vice President of the Ron Brown Scholar Program) to submit one more essay for the application, despite his own doubts. When both opportunities came to fruition, Saunders fell in love with the possibilities of education. He said the encouragement he received from the adults in his life left a permanent mark.

“Once you’ve taught someone to imagine an expansive life for themselves, you cannot take that away,” Saunders reflected.

Paying it Forward

After arriving in 2004, Saunders became an integral part of the Hopkins community, serving as a history teacher, Junior School adviser, and instructional coach. He also contributed through roles on the admissions committee, community service field trips, and educational efforts in New Haven.

It was through the Pathfinder program, however, that Saunders found the perfect opportunity to pay forward the encouragement he received as a child. Originally called Summerbridge and then Breakthrough, Pathfinder is a four-year, tuition-free academic enrichment initiative for high-achieving middle school students from New Haven public and parochial schools. It offers rigorous academic preparation, mentorship, and summer programming to help students succeed in competitive high school programs and beyond. It is not surprising why Saunders took to the program and its promise.

“There are so many kids who are smart enough, who work hard enough, and no one bothers to tell them how to imagine success,” Saunders said. “Our job as educators is to help them see what’s possible.”

Originally serving as a teaching fellow for Pathfinder while still an undergraduate at Yale, Saunders went on to hold every position at the program, often after advocating for the position to be added. He also conceptualized each position along the way. For example, while still an undergraduate, Saunders advocated for the Pathfinder Summer Program to have a dean of students, and once the role was approved, he designed the position along with the first code of conduct for the program. He also advocated for the Summer Program to have more robust mentorship available for teaching fellows and then designed the instructional coaching model—including writing the program’s first curriculum guide—which was used as a model for years.

Saunders eventually took over as Executive Director of the program in 2020 just as the pandemic was in full swing. 

During his time with Pathfinder, the program went from a single-grade program with 30 students to a comprehensive, year-round initiative serving 120 students from over 20 New Haven schools. His innovative curriculum design and mentorship enriched the program’s impact and provided professional development for local teachers, among other improvements.

To this day, Saunders lights up when he sees a Pathfinder alum making an impact in the world. He is always ready with a fresh story of seeing a Pathfinder graduate in action.

A Commitment to Community

At Hopkins, Saunders has been known for his thoughtful and inclusive approach to teaching and advising. Colleagues like Jocelyn Garrity, Director of the Junior School, have described his ability to make others feel seen and appreciated. 

“He’s genuine, incredibly thoughtful, and consciously works to make others feel included and appreciated,” she said. Saunders brought creativity and humor to School life, often dressing up in elaborate costumes for Junior School events and Pumpkin Bowl assemblies, staging snowball fights every winter on the quad, and always offering anyone interested with tips on restaurant recommendations and fun events in New Haven. Some colleagues have gone as far as dubbing Saunders the unofficial Mayor of New Haven.

“New Haven accepted me back,” he said. “It accepted this hopeful youth as someone who could make a life here.”

This full immersion in New Haven and the Hopkins community felt natural to Saunders, who smiled brightly when asked what made the people on the Hill special to him.

“You’re constantly surprised at how brilliant your colleagues are,” he said. “It’s very easy to respect your colleagues at Hopkins because they’re brilliant, deep-thinking, hardworking, goofy, and talented.” 

Beyond Hopkins, Saunders has served on boards of directors for numerous organizations dedicated to education, environmental justice, and building community, including the Ulysses S. Grant Program at Yale, Gather New Haven, Long Wharf Theatre, the Urban Resources Initiative, and Common Ground High School. His prolonged involvement in these organizations (and many others) reflects his belief that education and community engagement are interconnected. 

A Special Ceremony

In honor of Saunders’ contributions, the Hopkins Medal ceremony brought together family, mentors, colleagues, friends, and former Pathfinder students. 

“When we thought about restarting this important tradition, Errol’s name immediately surfaced,” said Gwen Evans ’84, Chair of the Board of Trustees. “His devotion to Hopkins and to the broader New Haven community exemplifies what this honor is all about.”

Head of School Matt Glendinning echoed this sentiment: “I cannot think of somebody more deserving than Errol. His impact on Hopkins and New Haven is immeasurable.”

In speeches, colleagues praised Saunders’ ability to cultivate imagination and possibility in students facing barriers to educational opportunity. Josh Young, a science teacher, Co-Director of the Pathfinder Summer Program, and a Head Adviser to the Hopkins Class of 2026, reflected on Saunders' impact as a mentor and leader. “Errol’s presence made our team stronger,” Young said. “He’s the type of adviser who is gleeful with pride when his students succeed. His joy is contagious, and his commitment to his students is unwavering.”

The evening’s program featured musical performances by Hopkins students, including Daniil D. ’30 performing Beethoven’s Piano Sonata No. 8 Pathétique (II. Adagio cantabile), and a Mozart Flute Quartet (K. 285) performed by faculty member Naomi Senzer (flute), Eleanor L. ’25 (violin), Ailene L. ’28 (viola), and Jaden L. ’25 (cello).

The ceremony concluded with the presentation of the Hopkins Medal, marking Saunders’ departure as he prepares to join the Cambridge School of Weston this fall. 

A Lasting Legacy

As Saunders transitions to his new role, he leaves behind a message woven into the fabric of Hopkins. “The Hopkins you leave behind is a better place for having benefited from your presence,” Evans said. “And we will miss you.”

Saunders expressed confidence in Pathfinder’s future under Anabelle Marty Jose, a Pathfinder alumna and incoming Executive Director. “It’s her ship next year,” he said. “I’m excited for her to imagine the next steps.”

Standing on that stage, proudly wearing the Hopkins Medal, Saunders was able to finally pick his head up from his work, and appreciate what he has helped create.

“I rarely think about my work at Hopkins being reflected at Hopkins. My first instinct is all about the kids and where they are and what they do,” he said. 

His belief that education can empower students to envision new futures, just like it has done for him, remains central to his legacy. Wrapping up his remarks, Saunders left the APAC audience with a motivational directive.

“Every single time you think, ‘That’s too much work, I will not do it,’ but it would help a kid imagine themselves better—DO IT!” 

The Hopkins Medal is awarded periodically to a member of the Hopkins community in recognition of unparalleled commitment, devotion, and loyalty to the School. It is the School’s highest honor and has only been awarded 23 times since its inception in 1994.

1994 F. Allen Sherk

1995 John M. Heath

1996 Elizabeth Bradley Benedict 1940 DAY

1997 Anna Bowditch

1998 Paul M. Weissman 1948 HGS

1999 Thomas Rodd, Jr.

2000 Kenneth A. Paul, Jr. 1968 HGS

2001 Vincent A. Calarco

2002 Susan Wintringham Crosby 1955 PHS & Sumner McK. Crosby, Jr.

2003 Mark G. Sklarz 1963 HGS

2004 John C. Malone 1959 HGS

2005 William J. Kneisel 1965 HGS

2006 Peter H. Wells

2007 David F. Swensen

2008 Noreen McCartney Haffner

2009 The Reverend John Davenport

2010 Jane Aries Levin and Richard C. Levin

2011 Linda Calarco

2012 David I. Newton 1967 HGS

2013 Barbara Hanscom

2014 Thomas A. Parr Jr.

2019 Richard A. Ferguson 1963 HGS