Matty Jacowleff
Coach Matty Jacowleff serves as the 15th Head Coach in Staples Football’s 100+ year history. A highly accomplished coach, Coach Matty was named the FCIAC Assistant Coach of the Year in 2022 and has earned four State Championships throughout his coaching career.
During his first season as Head Coach, Coach Matty was named the New York Giants Tri-State Head Coach of the Week after the Wreckers defeated Darien for the first time in 13 years. Coach Matty is also a finalist for the 2026 Westport Public Schools Teacher of the Year Award.
Before being named the Head Football Coach in 2025, Coach Jacowleff was the Offensive Coordinator, Wide Receiver and Defensive Back Coach at Staples. Under his guidance, the Wrecker Wide Receivers have rewritten the record books. In 2021 and 2022, the team set new records for the most receiving yards and touchdowns in a single season. In both 2022 and 2023, Staples led the FCIAC in receiving yards, with the Wreckers also finishing #1 in the state for receiving yards in 2022.
Coach Matty's defensive backfield had a historic 2023 season, with the Wrecker Defensive Backs allowing just a 49% completion percentage. Opposing offenses averaged only 131 passing yards per game and scored only 10 touchdowns against a state-leading 21 interceptions. Over the past four seasons, the Wreckers have scored 100 touchdowns through the air while allowing just 33 passing touchdowns and recording 61 interceptions—the most in the state over the four-year span.
Coach Matty has mentored multiple Staples Football Wide Receiver and Defensive Back alumni, who are currently playing for Division I FBS programs at Syracuse University, Wake Forest University, University of Michigan, Fordham University, the University of Delaware and Duquesne University.
A number of individual receiving records have been set under Coach Matty’s tutelage:
Top four receiving yards in a season: Tyler Clark (2022), Shane Sandrew (2024), James Hillhouse (2022), Nick Armentano (2021)
Top three receptions in a season: Tyler Clark (2022), Shane Sandrew (2024), James Hillhouse (2022)
Single-season receptions leader: Tyler Clark (80, most in New England in 2022); Shane Sandrew (80, third most in New England in 2024)
Career receiving yards: Nick Armentano (2021), Tyler Clark (2022)
Career receptions: Nick Armentano (2021), Tyler Clark (2022), Shane Sandrew (2024)
Most catches in a single game: Tyler Clark (2022) and Shane Sandrew (2024)
In the past four seasons, 28 WR/DB players have earned All-FCIAC honors under Coach Matty's leadership. In 2024, Shane Sandrew was named to the All-State First Team as a Wide Receiver, and in 2023, Safeties Sam Petrosino and Max Maurillo were selected to the Connecticut All-State Team. Additionally, in 2022, Staples Football made history with two WRs, Tyler Clark and James Hillhouse, named to the Walter Camp Connecticut Team—the first time in the award's history that two players from the same team earned this honor.
Coach Matty is also committed to developing well-rounded student-athletes and leaders. Over the past five years, five Staples Football graduates have gone on to attend the United States Military Academy at West Point. Outside of football, Coach Matty is a Varsity coach with the back-to-back State Champion Staples Lacrosse Program.
A proud alumnus of Staples High School, Coach Matty was the Captain of the 2014 football team and played linebacker for the Wreckers. After high school, he earned a Business degree from Northeastern University and a Master’s in Education from Fairfield University. He currently resides in Westport, teaches at Staples High School, and is the proud owner of his English Bulldog, Blitz.
Paul Philpott
Coach Paul Philpott has served as the Defensive Coordinator for Wrecker Football since 2020. Under his leadership, the Wrecker Defense set an all-time school record in 2024, allowing just 6.42 points per game. The defense also held opponents to an average of 2.9 yards per carry and forced 26 turnovers. In the 2023 season, which saw the Wreckers claim the State and FCIAC Championships, Coach Philpott's defense allowed only 11.3 points per game. In the State Semifinal, the Wreckers shut out the state’s #1 scoring offense, Southington, to advance to the Championship game. In the final, the Wreckers defense stood firm and stopped West Haven’s 2 PT attempt to win the Connecticut State Football Championship and finished the season ranked as the #1 team in the State of Connecticut.
In 2024, Coach Philpott was selected as the FCIAC Assistant Coach of the Year. He was also recognized by the Big New England Football Clinic as the 2025 Assistant Coach of the Year for
Coach Philpott’s association with Wrecker Football spans decades. He was a member of the coaching staff from 1993 to 2000, including the 1997 FCIAC Championship team. His son, Rob Philpott, a 1996 graduate of Staples, is a proud member of the Staples Football Hall of Fame.
After graduating from college, Coach Philpott was commissioned as an officer in the U.S. Marine Corps, where he served as a Naval Aviator for 20 years, including combat service, and retired with the rank of Lieutenant Colonel. Following his military career, Coach Philpott transitioned to the private sector, where he worked as an executive in the health insurance industry.
Before returning to Westport, Coach Philpott gained valuable coaching experience in Southern California at Mission Viejo High School, where he served as a Defensive Assistant, coaching linebackers. He also served as Defensive Coordinator at Daniel Hand High School. Between 2017 and 2019, the Hand Tigers compiled a 37-game winning streak (the third-longest in state history) and won two State Championships. During that stretch, Coach Philpott's defense allowed an average of fewer than 7 points per game. Over his 11 years at Hand, the program won a total of four State Championships.
In addition to his three sons and two step-sons, Coach Philpott is the proud father of Winnie, his Old English Bulldog.
Robbie Milne
Coach Milne returns for his second season as the Offensive Coordinator for the Staples Football Wreckers.
Coach Milne began his high school coaching career in 2014 as the Assistant Freshmen Coach at Shelton High School. In 2016 he took on the role of Head Freshmen Coach, while also contributing as an assistant coach for both the varsity and junior varsity teams.
In 2019, Coach Milne expanded his coaching repertoire by serving as the JV Head Football Coach & Varsity Wide Receiver Coach at Staples High School, followed by a two-year stint as the Linebacker Coach in 2020 and 2021. This diverse experience allowed him to gain a deeper understanding of the game and hone his skills in various positions.
From 2022 to 2024, Coach Milne held the position of Associate Head Coach and Offensive Coordinator for Shelton High School, where he played a leadership role in developing game strategies and mentoring players. In addition to his high school responsibilities, he served as the Director of Football for the AYF youth league, fostering a love for the game among younger athletes.
Beyond football, Coach Milne is also deeply involved in coaching youth and high school lacrosse, emphasizing the importance of teamwork, discipline, and sportsmanship in all his coaching endeavors.
Residing in Monroe with his wife, Shannan, and their dog, Lucy. Coach Milne is committed to making a positive impact on the lives of young athletes both on and off the field. He believes in the power of sports to teach valuable life skills and is dedicated to helping each player reach their full potential. We are excited to welcome Coach Milne back to Staples Football as we continue to build on our tradition of excellence.
Ryan Connors
Coach Ryan Connors is in his 8th season coaching Staples Football. Coach Connors serves as the Co-Defensive Coordinator and leads the Linebackers. Coach Connors has coached multiple Linebackers to the All-FCIAC and All-State teams. He is a 2015 Staples graduate and played three years at the Varsity level as a Defensive Back and Linebacker. Coach Connors is currently taking class to receive a Master’s Degree in Education. He currently works at Staples High School and resides in Westport.
Corbett Smith
Coach Smith enters his fourth season on the staff and third as the Special Teams Coordinator. In 2023, Smith’s Special Teams excelled in several categories. Most notably, Josh Marcus led the state with a net average of 42.4 yards per punt.
Smith also assisted Coach Horton with the team's kickers and punters. In 2023, Staples Kicker Max Maurillo connected on 54-of-56 of his PATs (96.4 percent), and 2-of-3 field goal attempts. In the punting game, Staples’ Punter Josh Marcus punted 28 times for a net average of 34.7 yards and notched 10 punts inside the 20-yard line, both ranked among leaders in the state.
Smith is a native of Lyman, ME, south of Portland where he was an All-Conference Wide Receiver and Returner for Head Coach Kevin Kezal at Thornton Academy. Smith attended the University of Maine and currently works in Corporate Development for Northwinds Services Group while residing in Weston with his wife.
Nick Chacho
Coach Chacho is entering his second season with Staples Football as Quarterback Coach after serving as Offensive Coordinator at Masuk High School, where he helped lead the team to a State Championship. During his time at Masuk, he played a key role in developing award-winning quarterbacks and one of the top offenses in the state.
Ron Clarke
Coach Ron Clarke is entering his ninth season on staff with Staples Football. Coach Clarke is in his fourth season coaching the Defensive Line. Under his guidance, the 2023 Staples Defensive Line saw massive improvement while Charley Leahy earned a spot on the All-State team. Coach Clarke has had four sons go through the Staples Football Program. Sean Clarke (2020 Captain) now plays Tight End at Richmond while Owen Clarke (2020 Captain) now plays Defensive End at Brown University. The former Fairfield University Baseball player has coached Baseball as well and has served on the Board for Westport Youth Baseball as well as serving in a variety of roles for the Gridiron Club, Staples Rugby and the Staples Matmen.
Isaiah Deloatch
Isaiah DeLoatch enters his first season as the Offensive Line Coach at Staples High School following the completion of his collegiate playing career at Central Connecticut State University in 2025.
During his career at CCSU, DeLoatch served as a Team Captain and earned numerous accolades, including two-time 1st All-NEC honors, All-New England recognition, and All-American Honorable Mention honors. Known for his toughness, consistency, and leadership, he helped anchor the Blue Devils’ offensive line throughout his collegiate career.
In his first season on the Staples coaching staff, DeLoatch is excited to work with the offensive line and help players continue to develop both on and off the field. After recently finishing his collegiate career, he brings current playing experience and a firsthand understanding of what it takes to compete at a high level.
Skip Lane
Coach Lane joins the Wreckers Coaching Staff for his first season in 2026. Born and raised in Westport, Coach Lane is a Staples Football Hall of Famer. Skip is the son of Coach Paul Lane, Staples Head Coach for 30 years. Skip played Quarterback at Staples and Quarterback and Defensive Back at Ole Miss. Coach Lane went on to play professionally for the New York Jets, Kansas City Chiefs, and Washington Redskins in the NFL.
Coach Lane has been working in the commercial real estate business for 30 years and currently works at Cushman & Wakefield in Stamford.
With Coach Lane’s deep ties to the history of Staples Football, we are excited to see the impact he will have.
Anthony Montiero
Coach Monteiro joins the Staples Football staff for his first season in 2026. Coach Monteiro brings a tremendous passion for football and a relentless desire to learn and grow as a coach. Coach joins the staff after coaching at Brien McMahon last season.
Football has been a lifelong part of Anthony's life. He was mentored by his grandfather, longtime coach Pete Tucci, who introduced him to the game and instilled in him the values of hard work, discipline, and servant leadership. Those experiences sparked Anthony's love for coaching and shaped the approach he brings to developing young athletes.
Anthony is committed to building meaningful relationships with players, creating a positive team culture, and helping student-athletes grow both on and off the field. He is excited to continue learning from experienced coaches while making a positive impact on the Staples Football program.
Dan Petrsoric
This is Coach Petrsoric’s first season coaching the Running Backs at the Varsity level after two years on the Freshman staff.
Coach Petrosoric is also a Special Education teacher at Coleytown Middle School. He joined the Staples Community in the Spring of 2024 and has been the freshman lacrosse coach for the past 3 years.
In addition, he also coaches Westport Youth Lacrosse, helping develop the next generation of Wreckers. Coach Danny grew up on Long Island where he attended Plainview-Old Bethpage JFK High School. Graduating in 2018, He was a multisport athlete, playing both soccer and lacrosse. During his time there, he was an all-conference midfielder and a two season captain of their varsity lacrosse team. Coach Petrsoric also received All-conference honors as a center back and was a one year captain of the school’s soccer team. After high school, he made the move to Connecticut to attend UConn where he received his bachelors and masters degrees in Special Education from the Neag School of Education.
Andrew Prophet
Coach Andrew Prophet enters his fourth season as a Staples Football coach, leading the Defensive Line.
Coach Prophet grew up in Norwalk, CT and then played football at St. John’s Univeristy. After receiving his master’s degree from St. John’s, Coach Prophet coached in the Norwalk Youth Football program before becoming the President of the Norwalk Football Junior program in 2021.
Coach Prophet also has a long career working in the insurance and financial planning industry.
Steve Anderson
Coach Steve Anderson has been the Head Coach of Staples Freshman Football since 2018. Coach Anderson began his coaching career in the spring of 2005 when he went back to Trumbull High and helped bring Trumbull to a Division II State Championship. He later went on to be an assistant Varsity Lacrosse Coach at ND-West Haven for 7 years. Coach Anderson has also coached girls soccer and boys basketball through the Connecticut Interscholastic Athletic Conference for the past seventeen years totaling over 40 seasons. In addition to coaching the Freshman Football team, he is currently the Assistant Varsity Lacrosse Coach of the State Champion Staples High School and is coaching Youth Lacrosse with Westport PAL. Coach Anderson is also the grade director of the 2030 Eclipse Lacrosse Club. Coach was a two sport athlete at Trumbull High School where he participated on the Football and Lacrosse team and was named All-FCIAC for both sports. Anderson continued his playing career at the University of New Haven where he competed on the Men's Lacrosse team. He also continued his football career playing semi-professionally out of New Haven until 2015.
Pat Ciquera
This is Coach Ciquera’s second year with the Staples Football Program, joining the staff as an assistant coach. A 2020 graduate of Staples High School, Coach Pat was a standout two-sport athlete during his time as a Wrecker, competing in both football and lacrosse. After graduation, he went on to play Division I lacrosse at Bucknell University, where he continued to grow as both an athlete and a leader. Coach Pat has returned to Westport and is currently an assistant coach with the Staples Varsity Lacrosse team, who recently captured the State and FCIAC Championship. His experience at the collegiate level and his deep connection to the Staples community bring a valuable perspective to the program, and he is excited to help mentor the next generation of Wreckers.
Mike Connors
Coach Connors enters his second year with the Staples Football Program as a Freshman Defensive Coach. A 1978 graduate of Staples High School, Coach Mike is a proud Wrecker alum who played for the Staples Football team during his time as a student. He has been a staple in the Westport football community for nearly two decades, coaching with Westport PAL Football since 2005. Through his years of involvement, Coach Mike has helped mentor and develop countless young athletes as they began their football journeys. His passion for the game and dedication to the Westport community make him an invaluable addition to the freshman coaching staff.
Chip Meyer
Coach Meyer enters his second year with the Staples Football Program as an assistant with the Freshman team. Prior to joining the Wreckers, Coach Chip spent numerous years coaching and leading the Norwalk Youth Football program, where he played a key role in developing talent at all levels. During his time in Norwalk, he coached several standout athletes, including current UConn running back Cam Edwards. Coach Chip brings a wealth of experience, passion, and energy to the field, and his proven track record of mentoring young athletes makes him a strong addition to the Staples coaching staff.