Getting to know Mr. Cummings
Assistant Dean of Students Mr. Cummings stands alongside Mr. Musanti, Principal of Monsignor Farrell High School.
Mr. Cummings, Assistant Dean of Students, has seen it all in over 30 years of Farrell experience
Throughout a career that spans over 30 years , Mr. Cummings has taught and led countless students, seeing firsthand the changing dynamics in both the classroom and the general school environment.
Mr. Cummings has seen a lot in his 32 years at Farrell, serving as both a dean and a social studies teacher during that time, being both a teacher and an authoritative figure.
After originally retiring following the 2021-22 school year, Mr. Cummings returned to Farrell in 2024.
"Farrell has always been a part of my life," Mr. Cummings said.
In his first year at Farrell, Mr. Cummings was a history teacher; however, it wasn't long before he was offered the role of a dean. As a dean, he saw first-hand both student and parent behavior change over the course of time.
From left to right: Mr. Kennedy, '12, Director of Alumni Affairs, Mr. Tobacco, '90, President of Monsignor Farrell High School, Mr. Cummings, Assistant Dean of Students, and Mr. Cusick, '88, Director of Institutional Advancement and Development.
One of the primary aspects of Mr. Cummings's career, outside of his responsibilities as an assistant dean, is his dedication to the Easter trips.
What began as a simple question to the principal during his own junior year — asking about the possibility of a school trip to Spain — has now grown into a Farrell tradition. With encouragement from Farrell leadership, Mr. Cummings was able to successfully plan the trip.
In 1993, the first Easter trip to London took place. Over the years, this tradition has evolved into annual trips that have taken students across Europe, with the help of the ACIS organization, which handles most of the logistics.
However, the journey wasn’t always consistent and there were some challenges. There were significant pauses, such as after 9/11. Even when flights were resumed, such an event made it difficult for parents to let their children fly without them. The other break was due to COVID and lasted between 2020 and 2022.
"Farrell has always been a part of my life"
- Mr. Cummings, Assistant Dean of Students
Despite these years where there were struggles, the Easter trips have continued to happen and grow, now nearly 1,500 students participating over the years.
Planning these trips, especially moving large groups of students, has proved not particularly easy, specifically in the past decade. But with the help of dedicated chaperones, the logistics and overall control of the trip became significantly easier.
Mr. Cummings acknowledges that the success of these trips wouldn’t have been possible without support from other members of the Farrell leadership team and faculty who help serve as chaperones.
Mr. Cummings originally retired following the 2021-22 school year but returned in 2024.
The influence of such an event stems directly from Mr. Cummings's own love for traveling.
"I've taken a Viking River Cruise from Sweden to Barcelona," Mr. Cummings said. "I also planned a cruise around Ireland.
Though his professional focus has been on education, Mr. Cummins is also an avid sports fan, with basketball being his favorite sport to watch.
Even with his retirement being short-lived, Mr. Cummings chose to stay and continue working at Farrell for his passion and dedication to the school. And we thank Mr. Cummings for his time and efforts.
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