Alumni Connections: Greg O'Brien '99 and Roy Dow '99

Alumni Connections: Greg O'Brien '99 and Roy Dow '99
Mary McNulty

In honor of Valentine's Day we thought it fitting to celebrate the unique relationships that are created or made because of Carroll. Over the years we’ve heard so many stories from parents, grandparents, students and alumni about enduring bonds of friendship and meaningful connections to the Carroll community. Following is our first installment of Carroll Connection stories!

Greg O’Brien ’99 and Roy Dow ’99: Lifelong Friends

Greg and Roy became friends their first year at Carroll when they were in the Gatehouse (5th grade). It just so happened that, with the exception of one tutoring block, their schedules were identical. That first year they sat next to each other in every class and became good friends rather quickly. Luckly, their hometowns were near each other which made it easy for them to get together outside of school, on weekends, and in summers during their Carroll years.

After Carroll, their parents played a big role in Greg and Roy being able to stay so close. Roy went back to public high school and Greg went off to boarding school in New Hampshire. They would talk often while Greg was away at school, calling or emailing when they could, but they always got together during school vacations. Their parents, committed to making sure they could see each other as often as they could, would drive them back and forth from each other's houses at all times of the day and night.

Now, in adulthood, they are as close as ever. They followed different career paths and have so many varied interests but their friendship has endured. When asked about how they've stayed connected, Greg states " Anyone that has met Roy knows why I keep so close to him." They talk a great deal and often ask each other for advice and opinions on issues in their lives (Roy refers to Greg as his in-house counsel and pays him in gear from the soccer teams he coaches). Roy says, “I think having gone through a difficult experience like we had with school connected us and is the anchor to our friendship. Over the years, that connection has continued to evolve and grow as we have lived and worked in different states and different careers. Out of the plethora of things I owe to Carroll, my friendship with Greg, and his family, is at the top of that list.”

Many of you may remember Greg and Roy from the New Parent Seminar, where they have both participated in the alumni panel for an impressive number of years. Their enduring friendship certainly makes them a compelling duo on this panel!

Greg is an attorney at DraftKings supporting the commercial operations of the company. Prior to DraftKings, Greg was an attorney in the financial services industry focusing on procurement, technology, and general corporate law. After his four years at Carroll, Greg went on to graduate from Proctor, University of Colorado Boulder, and BC Law School. He is a trustee at Dean College in Franklin, MA. Greg joined Carroll's Board in 2020.

Roy is a Special Education teacher at Newton North HS. An accomplished soccer coach, he is co-founder of Prep Soccer Academy. After his four years at Carroll, Roy went on to graduate from Belmont HS and Wheaton College where he studied Education. He earned his master’s degree in Special Education from UMass Boston.

Tell Us Your Story!

We want to hear about your Carroll Connections. Are you still in touch with your Carroll friends? Do you have an interesting story that connects you to Carroll? Have you crossed paths with other Carroll folks in your life (work, community, school, etc) Quirky, heartfelt, awe-inspiring, interesting, or nostalgic - we can't wait to hear from you! Please email your stories to Mary McNulty at

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