Andrew Rotondi, Class 1997

A move to New York City ultimately turned out to be a life changing experience for Andrew Rotondi. Living with his brother and friend in NYC, Andrew started to pursue his passion of writing, acting, and producing films. Two years ago, Andrew moved back into the area to Medford, where he continues to write and sell real estate. His experiences at Winchester High School and in the community have helped shape him as a person but also professionally in his writing.

What are you doing now? Where are you currently living?

I am currently living in Medford and am getting my real estate licensed here. I was in living in New York City for years doing real estate, which is how I ultimately paid for my first feature film. I came back to Massachusetts two years ago.

What connection, if any, do you still have to WHS or the community?

I think I’ll always have a connection to Winchester. Our family has been here for a long time. My brother Matt and and my sister-in-law Heather live in town. My niece Madison, who is a sophomore, just attended the senior prom. Winchester will always be home. I’ll get a place here at some point just to keep up the tradition.

Was there a favorite moment, person or experience at WHS that you remember that has helped you find your passions or reach your goals?

As a writer, simply the experiences that I had in this town that I now write about. For instance, the feature I am trying to get done now “Journey To The Green Monster” is about two friends who have a fake fight in the middle of the hallway to get suspended from school. During our senior year my friend and I had nine absences near the end of school year and couldn’t attend senior skip day. We were informed earlier in the day that suspension does not count as an absence. The rest as they say is history. We went at it in the middle of the hallway and got a three day vacation. I think it’s important to point out that my friend was the #1 heavyweight wrestler in New England!

But so many teachers Winchester produced and continues to produce have such a strong impact on lives. You don’t necessarily realize it at the time. Mrs. Innes, Md. Hannawalt, Dr. Benton and so many others molded us and helped us grow. Winchester is really a great town. Even though we all complain about our towns growing up, you certainly appreciate it later in life.

What was the path you took to get where you are today?

I think when I left for NYC to live with my brother Todd. We were in a East Village studio no bigger than a couple bathrooms. He was on a soap opera at the time. I was thrown into that world. Our friend Billy Branley, another Winchester alum, living in New York at the time, had finished his first screenplay. I remember reading it and thinking I could do this too. That was the start of my writing which ultimately lead to acting, producing, and directing.

Please share a success since leaving WHS.

My biggest success was getting the feature film done, “The Blood Painting.” Here is a link to the trailer: https://vimeo.com/181539027. I closed a pretty big deal in NYC and left for home to film. I spent my life savings on it. All my writing is primarily based around here. Write what you know, they say. Now my sights are on getting my next feature done. It is a monster but I’m starting to meet the right people.

Is there insight or advice you can share with current students?

Appreciate the town you come from. It’s a great launching pad and creates a lot of great people.

Keep God first in your life. Always stay humble. Learn from your failures. You’re going to get beat up but just put your head down and plow through. Life is a journey. Enjoy it!