Gregg Reilly: A Passionate Musician, Coach, and Teacher

By Amy Khaing ’27

Outside of math class, Mr. Gregg Reilly is known for his involvement and passions in a myriad of places: the ice rink, outdoors, the kitchen, and the stage. Whether it be skiing, mountain biking, golf, live music, playing guitar, cooking, mathematics, reading, 3D printing, or DIY projects, Mr. Reilly “always enjoys testing the boundaries of what [he] already knows or can do.” As he notes, “a common thread in all the above [interests] is the fact that each is an inexhaustible font of opportunity for growth, connection, and exploration,” while also providing him “tangible problems to solve.”

Mr. Reilly developed his passion for music, specifically the guitar, in his forties. He notes how he “has always loved music” and has been able to bond over this passion with his students. Particularly, as a tutor, Mr. Reilly remembers how when he started working with a student, Brooks, he was able to find a “nice common ground for building trust” because they both “loved music and [were] avid guitarists.” Because of their shared interests, Brooks thrived in the months that followed. Unfortunately, Brooks passed away suddenly after returning from a family trip to Peru. Mr. Reilly recounted how it “was such a devastating loss,” but after his wife “surprised him with a guitar on his next birthday,” he has been playing guitar every day since. Mr. Reilly added that he still “thinks of Brooks often,” and because of the bond that he formed with him through music, he felt “constantly challenged to learn new techniques, songs, licks, styles [...] to play with other musicians effectively and supportively.”

Indeed, what inspired Mr. Reilly to pursue teaching in the first place was the connection he could build with students. Around halfway through earning his Applied Mathematics degree, Mr. Reilly began to deliberate on “the aspects of life that gave [him] joy and purpose.” Through those reflections, he realized that one of the biggest motivators for him in learning math was “the desire to understand so [he] could in turn explain it to others.” “Looking back over the last 41 years,” Mr. Reilly notes,” he still “smiles at the wonderful insight that 20-year-old me had.” He still gets “great joy over watching a student puzzle over a ‘tricky’ concept and then having that ‘aha!’ moment.”

In addition to teaching math, he coaches sports such as JV hockey at Milton. Some of Mr. Reilly’s favorite memories at Milton happened in the rink. He remembers “the excitement and joy that so many young women experienced through Girls’ JV Puck.” What he loves most about Milton, though, is “the way that students and faculty are celebrated for their whole selves,” whether they are athletes, musicians, thespians, or academics. The diversity of the students and faculty helped Mr. Reilly “broaden his perspective,” in which he was “able to understand the world in a much deeper way.”

Mr. Reilly added that, within his five years at Milton, he has found “Milton to be a uniquely quirky place.” There are no constructs or stereotypes for what a “typical Milton student or teacher” should look like, and he hopes it “remains so in the years to come.” Having spent over the last forty years teaching and “planning the experiences of my students both over the short and long term,” Mr. Reilly is “looking to embrace the unknown and enjoy the freedom of a less regimented schedule” in the next chapter of his life. Meanwhile, he will “always remember the kindness, intelligence, and curiosities of the countless colleagues and students [he has] worked with over the years.”