Class of 1997, Jason Caldwell

Oliver Steinman, Staff Writer

When Director of Admissions Jason Caldwell ‘97 P’28 was in high school, he recognized the disparities in the education system comparing his educational experience with that of his peers in his old neighborhood in the Soundview section of the Bronx.

“At its best education is the great equalizer; it can raise someone’s station in life,” he said. This realization is what drove Caldwell to pursue a career in education, and ultimately led him back to work at his alma mater.

Caldwell entered the school as an eighth grader in 1992. Caldwell struggled to adjust to the school’s demanding academics. “At my old school I was valedictorian, and school had been pretty easy,” he said.

Caldwell discovered he was good at sports and joined the football, basketball, and track and field teams. He was particularly successful at football and became a captain in his senior year, he said.

In addition to playing  three sports, Caldwell participated in a variety of different clubs. He was  head of the orientation committee, President of the Union, co-chair of the Cross Cultural committee, and participated in theater in 8th, 9th, and 10th grades. The Union, which provides a safe space to discuss issues faced by students of color, was particularly important to Caldwell, he said.

During his time at the school, it was hard to pick and choose his activities. Caldwell’s busy schedule meant he had to give up certain activities he enjoyed so that he could prioritize others. “I had to give up theater for track,” he said.

Caldwell’s favorite subject was physics, but also enjoyed discussing literature in his English classes, he said.

The most valuable experiences Caldwell had at the school,  however, were not in classes, but through the friendships he made, he said.

“Something that I talk about at every open house is that 29 people who graduated HM were at my wedding,” Caldwell said.

Caldwell implemented the most important lessons he learned at the school in college, including teamwork, writing skills, time management, work ethic, community, but most of all how to be a good friend, he said.

Compared to his years as a student, the school is bigger, more diverse, and feels more like a community, Caldwell said.

“This is the main reason I chose to send my daughter here,” he said. “This type of community is one that looks out for one another and genuinely feels like a family.”