Rarely does a season unfold exactly as expected, and for the Staples High School football team, this fall proved no exception. After years of sustained success and deep postseason runs, the Wreckers faced an unfamiliar challenge in 2025, finishing with a losing record for the first time since 2019.
Coming off two successful seasons capped off by deep playoff runs, expectations for this year’s group were high; they retained several key starters, including quarterback Nick Weil ’26, running back Chaz Darby ’26 and wide receiver Charlie Clark ’26.
However, the most notable storyline of the Wreckers’ offseason would be promoting Matthew Jacowleff ’15 to become the youngest head coach in Wrecker history. Before his promotion, Jacowleff had served as Associate Head Coach under Adam Behrends. Early on in his tenure, Jacowleff expressed a desire to continue the Wreckers’ legacy of success.
“Staples Football, to me, is and always has been the best program in the state of Connecticut; my goal is for everyone in our area to know that,” Jacowleff said after his promotion in May.
(Will Enquist ’26)
The Wreckers would get out to a hot start to their season taking decisive victories against Glastonbury and Stamford, but the Wreckers’ third contest, against West Haven, proved to be among their most thrilling games this fall.
The Wreckers trailed the Blue Devils 32-34 late in the fourth quarter after a physical back-and-forth matchup. Running back Darby would make multiple bruising runs setting up a game winning Mickey Ross ’26 field goal as time expired that would see Staples fans storm the field.
“That moment is why you make all the sacrifices you make,” Jacowleff said.
The Wreckers would follow up their hard-fought win against West Haven with a dominant 31-6 win over Darien. It was at this point in the season with the Wreckers sitting at 4-0 that the team would see its fate begin to change. Staples would lose its next 5 of 6 games being outscored 116-46 over their last four games of the regular season, according to Maxpreps.
At 5-5 the Wreckers would narrowly qualify for the playoff with a first round matchup against the Greenwich Cardinals. The game was relatively uncompetitive, with Greenwich winning 41-7 in a contest that would see them consistently convert on third down while also maintaining significant pressure on the Staples quarterback.
“I wish it ended differently; I wish [there was] a couple of wins at the end of the year,” Jacowleff said. “I know what our program is destined for, it’s not if but when our program is going to win our next state championship.”
The loss to Greenwich in the playoffs would also mark the last football game for the class of 2026. Over their four years with the program the class would preside over a winning record and a state championship in their sophomore year.
“[The class of 2026] is a really solid, great group of kids,” Assistant Defensive Coach Ron Clarke said. “When you look at the personality of this class, what you are going to see is just a high character, high integrity group of kids that played very hard.”
Despite a challenging final season, many seniors on the football team retain a positive outlook on their experience with the program.
“I think [our] legacy will be the fact that we never lost the energy and enthusiasm to practice everyday even through the many losses,” Clark said.
Although the 2025 season may not have met the program’s high expectations, the Wreckers’ coaching staff looks forward to what the future holds for Staples football.
“The trajectory is going to be going up,” Ron Clarke said. “We’ve got a good solid course of kids coming up with some size. Matty is obviously going to get better at his job, he’s got a good young staff who are going to get better at their job […] so that aspect is going to be good.”
