Windward Alumni Profiles


Tom Hyland '05: Windward Was a Good Place

The Compass Fall 2012

“If you hear anything in the background,” Tom Hyland ’05 said, “it’s just Times Square!”

Reached by telephone on his lunch hour at Morgan Stanley, where he works in the prime brokerage division, the Windward alumnus and former cross country athlete took time to speak about his Windward experiences at what is termed the crossroads of the world.

“Windward helped me in all aspects of my life,” he said. “It was a good place where I was comfortable learning, and that was most important.”

Tom arrived at Windward in the fifth grade, but his early elementary years were spent at Murray Avenue School, a public school in his hometown of Larchmont, NY. He was a happy student, with many friends and good teachers, but even this did not take away the fact that something was wrong. “Things weren’t clicking by the end of fourth grade,” Tom explained. “My struggles were basically related to reading and writing, and my parents knew about Windward. It was a tough choice to leave [Murray Avenue], but once I got to Windward, I was very comfortable.”

First impressions mean a great deal, and Tom’s first impression of Windward has stayed with him. “I remember when I took the tour!” he said enthusiastically. “I remember how nice the building was, and how nice the teachers were, and it felt like a good place where I would do well. That’s what I really remember about Windward, how welcoming it was, and I really enjoyed my time there.”

Under the tutelage of faculty including Ms. Carol Leahy and Ms. Betsy Weiner, whom he describes as “very instrumental in my reading and writing development,” Tom’s academic skills flourished. He also honed his athletic skills during his time at Windward, taking part in both cross country and basketball. Mr. Chris Eberhard, currently the Assistant Head of the Middle School, served as both his math teacher and basketball coach.

“I played basketball growing up, both for my church and recreationally,” he explained. “In an organized sense, I’d been doing it for awhile. Cross country was my main sport at Windward; I ran in the fall and spring, and played basketball in the winter.”

The skills and confidence he gained in Windward’s classrooms translated onto the athletic field. He competed in track meets and basketball games against students from the Fairchester League, a consortium of independent schools located in Westchester County, NY and Fairfield County, CT. Although he loved running cross country, he sought to become equally proficient on the basketball court, citing the differences between the two sports and the challenges they presented.

“The biggest challenge for me, in terms of basketball, was improving. It’s important to remember how much teamwork is involved when it comes to basketball, as opposed to cross country,” Tom said. “You’re practicing as a group, but when it comes to the race, you’re on your own. I really learned to run at Windward; we had a really small, close-knit team, and it was a great place to run.”

The camaraderie of Windward’s classrooms and athletic teams, however, came to a close for Tom at the conclusion of his eighth grade year, when he graduated from Windward. Suddenly, he was faced with the prospect of returning to public school, and he was more than a little anxious over the idea of enrolling at Mamaroneck High School.

“Oh, I was absolutely nervous to go to public school,” he said. ‘It was going to be much bigger, and I didn’t know what to expect. I was definitely nervous because of that, and the homework. And the writing!”

While he moved seamlessly into academic life, the road to athletic achievement at Mamaroneck High School proved rocky. “After I graduated from Windward, I broke my leg pretty badly and couldn’t do any sports my freshman year. It probably set me back a year or so in regards to my athletic development,” Tom said. “Sports weren’t there as a safety net.” Nevertheless, Tom persevered, and by his sophomore year, he was a full-fledged member of Mamaroneck’s indoor and outdoor track teams, and remained an active participant through his high school graduation in 2005. He went to the New York State qualifying races on behalf of Mamaroneck High School, and clocked in at 4 minutes for an average milerun.

While he did not know it at the time, his running skills would eventually come in handy in a professional capacity. “Right after college, I did a two-year volunteer program via AmeriCorps,” Tom said of the national service program that matches prospective volunteers with opportunities to serve national and local nonprofit groups. He discovered the program while a student at Georgetown University in Washington, D.C., where he earned a B.A. degree in sociology in 2009. “Many times [AmeriCorps] will put you some place randomly, but I fell in love with the high school, applied, and volunteered there for two years.”

The high school in question was Cristo Rey New York High School, located on Manhattan’s Upper East Side. Part of the Cristo Rey Network, which operates 24 schools in urban centers nationwide, Cristo Rey New York is a co-ed college prep school serving students who have demonstrated the ability to achieve academic success, but who do not have the financial means to enroll in another private school. Although Tom had written his undergraduate thesis on education, he drew on his experiences in Windward’s classrooms when he arrived at Cristo Rey, where he taught courses in English literature and writing.

“In my first year, I was a teaching assistant, and in my second year, I had my own class,” he explained. “You’re on your own, and it’s definitely an eye-opening experience. I can’t think of a job right out of college that would give you stronger characteristics as a professional. It was a rich experience, and I’m very happy I spent two years doing it.

“Not every student is the same,” he added, reflecting back on the classes he taught. “It’s important not to treat every student like they’re the same. I know how important it is to have a good teacher and to give students the resources they need. Windward definitely helped me in the classroom and as a teacher.”

In addition to his teaching duties, Tom helped run Cristo Rey’s work-study office. As a complement to their academic duties, students at Cristo Rey report to work one day a week at various entrylevel jobs scattered throughout Manhattan’s most prestigious corporate companies. The jobs are designed to give students valuable employment experience while breaking the cycle of poverty. Tom was responsible for managing the jobs of every student in the school, at companies that ranged from McKinsey & Company to AllianceBernstein to HarperCollins Publishers. When the school day ended, he coached Cristo Rey’s handball and cross country teams.

“I’ve coached running and helped kids out,” he said. “Running’s great! I love it.” In his spare time, he has run the New York City Half Marathon, and recently participated in a race through Riverside Park to benefit Big Brothers, Big Sisters NYC.

Reflecting back on his Windward experiences from his office at Morgan Stanley, Tom had this to say of the School that changed his life for the better, enabling him to go on to do the same for others. “Windward is a great part of my life,” he said. “It doesn’t compare to any other school.”