After years of working his way through the Westport youth sports system, Jacowleff ’15 has been named the new head coach of Staples football. His promotion is the culmination of a nearly two-decade long journey marked by resilience, passion and unwavering dedication to the game and community that raised him.
Known to his players as Coach Matty, Jacowleff began his Westport football journey in 4th grade, picking up the sport on the advice of his father. On the field, Jacowleff quickly made an impact, contributing to successful Westport Wrecker youth football teams. After years of idolizing Staples football from the sidelines, Jacowleff would finally have the opportunity to represent the program he held so dearly.
“Going into my freshman year of football at Staples, putting on the Staples S for the first time, I really felt such a sense of pride and responsibility to the program to really leave it in a better spot,” Jacowleff said. “I felt so fortunate and blessed to have the opportunity to wear a jersey that meant so much.”
Jacowleff’s time at Staples did not come without its challenges; delayed diagnosis of a bicep tear would sideline him through the entirety of his sophomore season.
“There were many times during that year where I wanted to quit because it was really difficult and it was a challenge for me and I am so glad that I wound up sticking with it,” Jacowleff said
After recovering from his injury, Jacowleff would continue to develop both his football and leadership skills as he tried to make up for his lost time on the field. Recognizing his work ethic and resilience, Jacowleff’s teammates would elect him captain for the 2014 football season.
“Coming back from injury, I was given some opportunities and was able to play a decent amount\. I was still getting caught up to speed, but again, I saw the value of leadership and I really put myself out there to try to better my teammates whether I was on the field or not […] which ultimately led to being elected as captain in 2014,” Jacowleff said.
In the end, Jacowleff helped lead the Wreckers to a 7-4 season, punctuated by a 38-21 Thanksgiving Day victory over Greenwich. Following his senior season, Jacowleff graduated from Staples and enrolled at Northeastern University.
In his second year of college Jacowleff fell severely ill, becoming hospitalized due to a heart issue. During this time, he felt isolated, afraid that opening up about his illness would either worry his parents or make him appear too vulnerable to his friends. Ultimately, it was this experience that drove Jacowleff to become a coach.
“I remember […] wishing that I had a coach that I could reach out to, that cared about me and would offer me advice, guidance and support in that moment and unfortunately I did not have that,” Jacowleff said, “It was in my apartment during those days I recalibrated my life because I wanted so badly to one day be that coach for somebody who was going through something similar.”
Jacowleff would begin coaching for Staples during his senior year of college in 2019. Since his hiring, he has worked in a number of positions for the football team, including associate head coach, head junior varsity coach, offensive coordinator, wide receiver coach and defensive backs coach. In 2022, he was named FCIAC Assistant Coach of the Year after helping the offense to record-breaking totals in both yards and touchdowns for a single season in Staples’ football history. Jacowleff works to build close relationships with his players off the field, making sure that he is more than just a coach for his players. Jacowleff can often be found in the halls during passing time checking in with his players.
“He makes it very obvious that he cares about us almost more as human beings [than] as football players,” Wide receiver Charlie Clark ’26 said.
Given his success, it was natural that Jacowleff would be a strong candidate for Head Coach following the departure of Adam Behrends to coach collegiate football as an offensive analyst at the University of New Mexico. Accordingly, on April 2, the Staples athletic department announced that Jacowleff had been hired as the new head football coach. “ [Coach Matty] loves the town, he loves the school, he loves the program, that came out loud and clear [in his interview],” Athletic director VJ Sarullo said.
In his new position, Jacowleff is tasked with continuing the success Staples football found under transformative former head coach Behrends. Jacowleff says that he is not trying to fill his shoes, but wants to continue to build the Staples Football legacy.
“I really can only try to live up to the standard of what this program is, and to put my best foot forward every single day and pour my passion, my love and support into every single player within our program, and focus on continuing such a strong legacy and tradition of Staples Football,” Jacowleff said.
Nearly two decades after beginning his football journey as a fourth grader, Jacowleff stands at the helm of the same program that shaped him. As he begins this next chapter, his mission is evident: lead with purpose, serve as a mentor for his players and leave the program in a better place than he found it.
“Staples Football, to me, is and always has been the best program in the state of Connecticut,” Jacowleff said. “My goal is for everyone in our area to know that.”
