The Board of Trustees of the Barbara Henry Courage in Teaching Award are honored to announce this year's Award Recipient.

2026: ​Olivia Castagno

Dean of Academics | Senior Math Teacher
Nativity Preparatory School - Boston, MA
Olivia Castagno is the Senior Math Teacher and Dean of Academics at Nativity Preparatory School in Jamaica Plain, MA. In 2020, Olivia graduated from Northeastern University with a degree in Health Sciences. After initially pursuing the medical field in college, Olivia realized her true passion was in teaching. That same year, she joined Nativity Prep as a teaching fellow while earning her Masters in Education at Boston College. After completing her fellowship in 2022, Olivia continued on as a lead teacher and has now been part of the Nativity community for six years. In the fall of 2025, she stepped into an additional role as Dean of Academics. Olivia is deeply committed to building meaningful connections with students and their families both in and out of the classroom. 
Previous Winners

2025: ​Laura Londoño

​Laura Londoño is a proud Colombian-American educator and advocate who immigrated to Boston at the age of five. A graduate of Boston Public Schools and Boston Arts Academy, Laura's own experiences navigating identity, mental health, and immigration deeply inform her teaching. After earning a full college scholarship at Emerson College, she began her career at Sociedad Latina, where she discovered a passion for empowering first-generation Latino students. Laura joined Teach For America and began teaching at Browne Middle School, where she is now finishing her fifth year. She pursued graduate studies at Boston University while teaching in the school’s dual-language program, where she courageously chose to teach in Spanish—reconnecting with her roots and modeling vulnerability for her students. Through classroom projects like student-published books and community celebrations, she creates spaces where students feel seen, valued, and empowered to lead.

2024: Oscar Gonzalez

​We continue our celebration of Oscar Gonzalez, the 2024 Barbara Henry Courage in Teaching Award Recipient. David Joseph, the former Executive Director of LA Scores wrote:
"Honestly, I couldn’t believe it. Here was this teacher from Palms Elementary School, who gave his own time for free, every single day after school. It was remarkable. In more than twenty years as an educator, I’ve never seen another teacher give this type of time so selflessly, so consistently, after the school day ended. But what made it even more impressive was that Oscar didn’t want a shred of praise or adulation or credit. This was the ultimate example of being great and showing courage in the shadows. He just wanted to help, to teach, and to do whatever he could to make the lives of these students better and assist them on their journeys moving forwards."
- David Joseph, the former Executive Director of LA Scores.

2023: ​Connell Cloyd

Connell Cloyd, originally from Memphis, TN, is a seasoned educator with almost two decades of experience. He holds degrees in Child Development (LA '03) and Education (BA '05) from Tufts University. Currently teaching middle school mathematics at the Henderson Inclusion School for 13 years, Connell believes in showcasing the real-life applications of math ensuring his students grasp its significance in daily living. Recognized with the nationally acclaimed Barbara Henry "Courage in Teaching Award," Connell goes beyond being an educator.  He has become a familiar face in the Greater Boston community by building strong bonds with his students and their families.

2022: Deborah Carlino

Meet the 2022 Barbara Henry Courage in Teaching Award Recipient: Deborah Carlino
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The inaugural Barbara Henry Courage in Teaching Award was awarded in 2022 to Elementary School teacher Deborah Carlino of the Martin Elementary School in South San Francisco. Deborah was nominated for the award because of her dedication to her students and her determination to uphold a legacy of justice. ​

Nominate a Teacher

Do you know a teacher who has gone above and beyond for their students? Nominate them for the Barbara Henry Courage in Teaching Award. If you know a teacher who has shown outstanding courage or compassion in the workplace or classroom, we want to hear their story, sing their praises, and consider them for the award.